Secret life Of James
Chapter 1
It was worth the wait halter top sun dress, her hair flowed around her face, framing it perfectly. My god, she was extremely beautiful. She floated down the stairs and all I could do was stare. Lily waltzed right up to me, wrapping her arms around my neck. She kissed me, "I have wanted to do that for so long, you have no idea," she smiled as our lips parted.
"Wow you look amazing." I took a couple of deep breaths. She gave me a twirl.
We went to a bar that overlooked a river, danced under the moonlight, had long conversations and drinks. I got to watch Lily's smile and gaze into her eyes. When We finished, I spun her out and then back in, pulling her close and finding her lips with my own.
It was almost four when we got to Lily’s home.
Without a word, she unlocked her door, and biting her lip, turned to face me. "Stay?"
I just nodded. Following Lily inside and up to her bedroom, I could feel the anxiety radiating from her, the eagerness, the fear, and the lust that went with it shone from her eyes. There was no hesitation. Lily pushed me onto the bed, pulling my shoes off and scrambling at my pants while I unbuttoned my shirt. Her top and bra were next, she took a deep breath, she had perfect breasts, she took a deep breath as I worked at the button and zipper on her jeans.
My underwear flew across the room, and I froze, watching mesmerized as Lily turned her back to me and slowly slid her panties down her legs, stepping out of the small pool of soft fabric and turning slowly. I couldn't move, the look in her eyes, that amazing body, the way she slowly crawled up from the foot of the bed, like a big cat on the hunt, slowly up my body, stopping to kiss my chest and then my chin, and then my lips, I wrapped my arms around her, my lips meeting hers, our tongues continuing our dance, there were no two-steps, no waltzes, this was a dance born of the gods, primal, raw, a dance begun before time, a dance of eternity.
My lips left hers as I pushed her onto her back, sliding my kisses along her cheek to her ear and then down the side of her neck, taking my time, teasing, and playing with each spot, trying to convince her it was the most perfect, the most erotic spot on her body.
Lily moaned, her hands roaming over my body as hers moved beneath me, her soft moans drifting to the heavens. Slowly down her collar bone to the valley between her perfect breasts, my hand finding one globe as my lips found the other, massaging and drawing tender circles around her nipple with my fingers as my tongue flicked the other and I sucked it into my mouth, biting it gently as I released it only to repeat the process as I shifted my kisses to her other breast.
Chapter 2
I woke up alone in Lily's bed. I could smell the coffee from downstairs, so I got up, grabbed a satin robe from the bedpost, and went downstairs to find her. There was a note, but no Lily,
James,
Thank you for last night. Sorry to run off, but I have patients early today.
Make yourself at home.
Lily
XOXO
My phone buzzed. It was Lily. "Dinner tonight, my house 7?"
"See you then," I texted Lily back.
I knocked on her door at 7, clean jeans, a light blue shirt, and sneakers. The smell of something wonderful filled my head when she opened the door, her smile filled my heart, and the kiss she gave me.
We were naked on the couch before we started dinner. She undressed my pant and swallowed me whole and then did things to my cock with her lips and tongue that was incredibly magical, refusing to let me finish, she tortured me forever. I loved every minute. When I finally pushed her onto her side and started licking her divine opening, her juices covering my face. We found ourselves covered in sweat.
She bit my lip, letting out what I can only describe as a soft growl, her hand found my head and whispered, “Fuck me, James”.
I make my way kissing her soft body, breast and back kissing her lips, my body on top of her lining my erection to her opening, she buried her lips in mine. Guiding me inside her, pinning her hands over her head, I thrust in and out of her yearning hole. With her moaning into my ears. I felt the muscles insider her convulse as her hand clutch the sheets. Warning me to not stop. I felt her orgasm, which pushed me over the edge I exploded inside her, collapsing on her.
Lily and I stepped into the tub. She joined me and leaned back against me. We sat quietly in the hot water, her body against mine, sipping wine, exploring each other with our hands. She nestled her butt against my crotch.
I kissed the back of her head, inhaling deeply, filling my head with the smell of her shampoo. What started in the tub, quickly moved to her bed, lasting late into the night as we explored each other with our hands, lips and tongues, invisible trails of kisses and caresses all over her body and mine accented by moans and gasps and exclamations of pleasure, carnal delights filled our souls as one orgasm after another threw screams of passion and lust into the night.
The flavour of Lily's sweet juice mixed with my own lingered in my mouth. I had found it in our passionate kisses and in the very centre of her sex, as we shared ourselves with each other completely. Finally, exhausted, content, and a little sore, I collapsed behind her, pulling her close and falling into a sleep filled with dreams of her and me and what might be to come. Waking with Lily in my arms was the best feeling of all.
Lily and I just sat "This is nice, isn't it?" her hand found mine.
"It is just like I imagined" I smiled at her and nodded.
Lily and I were cuddling together in the bedroom room. Lily's arms wrapped around my waist. Kissed me and she asked to move in with her. I didn't rent a larger apartment cause i was hardly home. It was merely to keep my stuff. She did have a bigger house. So, i said why not. we were talking about the logistics of living together.
It seems great. But there was a secret I couldn’t keep much longer.
Sunday was a flurry of activity with getting packed and the movers moved my things into her place. Lily and I running back and forth to my house to get the remaining things back. I finished moving stuff into our house. She gave me space in the garage. As I was Storing the extra, I looked at the box and realised my secrets timeline just changed, I would just have to tell her soon before the secret gets out. I would not have a place to store a secret in her house
Ever since I graduated from college, Maria, my neighbour, was a close friend of mine. We've been neighbours since i moved after college. As movers loaded boxes into a truck parked in front of my house, Maria approached to offer her well wishes and extend an invitation to her upcoming wedding. Engaged in casual conversation, Maria suddenly shifted gears, her expression turning serious as she directed a pointed question at Lily: "Does he still wear women's clothing at home?" Caught off guard, I arched my eyebrows in disbelief, taken aback by the unexpected inquiry.
Lily suddenly looked over at me and back to Maria. I could see how uncomfortable she was as she finally spoke up, "Well no, this is the first I've heard about that side of James. He's never even brought it up and I'm sure it was just a phase."
Maria laughed “I used to ask him to water my plants when I travelled. For some reason he used to always come home dressed to the nines in girl clothes. The first time I saw I was shocked. I saw him on the home security camera. I thought he sent someone else” she stopped before she saw my face and said “oh no. I'm sorry I didn’t mean to stir problems. I thought she knew”.
Nothing else was mentioned and we spoke about other things. Lily seemed quieter than normal, and I tried just to let things play out. It was after we finished moving the boxes, back to her house that Lily started talking on their drive home.
Chapter 3
"Well, that was the last of the boxes.” I said as we got into the car and drove. I kept my eyes on the road, but I could feel she had something on her mind and waited for her to say what she was thinking. We continued to chat about the movers and the timeline. Then when I thought we were done talking, she asked the question that I knew was on her mind.
Your neighbor Maria is a character, isn't she?"
"Yes, Maria has a big mouth. I'm sorry if she made you uncomfortable."
"That was an interesting revelation I learned about you from Maria. Why didn't you ever tell me about that part of you, James?"
“I was too embarrassed to bring it up”.
I felt my stomach turn and a sharp pain in my heart. I was painfully waiting for this topic to come up, and I knew the moment Maria opened her big mouth that I would have a lot of explaining to do. I swallowed hard and tried to relax wondering how to explain this to her without her running away and how trying to hide this from her was a gigantic mistake.
She sat quietly as I drove home, contemplating what I had said. Lily was trying to be an understanding and good girlfriend. Hoping, this was something her boyfriend did years ago, and not part of him today. She tried to let it go.
Lily smiled and patted his leg and said, "I guess it's no big deal. It's not like you still dress in girls' clothes anymore."
I might have remained quiet for too long a time, as she took my hand and said, "You don't still dress in female clothes, do you?"
I've never been able to lie and when I do, I always get caught so I just didn't say anything as I continued to drive.
"James, do you still do that? Tell me!"
"Once in a while I'll put on a pair of pantyhose and panties under my work clothes for the day, just for the sensation." I blurted
She sat there thunderstruck with her mouth wide open, in complete shock. I knew I had to say something but not sure what would help but tried anyway.
"I just like how it feels and sometimes when I'm stressed, it helps to wear something feminine, that's all."
She was obviously distraught. I love her so much and would do anything to keep what we had up until now.
"Having to find out about this publicly available secret of yours was very surprising. I have questions and i expect complete honesty."
"I guess I tell you everything and hope you still want to be with me." I looked at her, my heart about to break.
"You said that you sometimes wear pantyhose and lingerie under your work clothes. Do you have your own lingerie?"
Gulping and realizing I had to answer honestly, I said, "I have my own things."
"Where did you buy these items?" she asked as she poured glass of wine.
"I ordered things from several places online, over a long period of time."
"Exactly what did you buy? What items?" She asked.
This was going to be difficult to answer because I only admitted to wearing pantyhose and panties, but I was about to come clean on much more.
"Some outfits. Some toys".
Lily’s attitude had changed her annoyance showing through her question as i answer without elaborating.. "James, my love, if you could be less cryptic, I mean how much more embarrassing can it get. You're holding back. Start talking. What's in the boxes?"
"OK, several dresses, blouses, high heels, wigs, makeup, nightgowns, dildos, butt plugs, and a couple chastity device."
She looked at me puzzled and shocked, "I thought you said you only wore panties and pantyhose under your regular clothes. Apparently, you weren't being honest before, were you?".
"Well, that part about the pantyhose under my pants is true, but sometimes I will put on an outfit when I'm alone at home. Sometimes I pack a special outfit to sleep in or just wear around the hotel room."
"How did this start? How old were you?"
"My fascination with all thing's women started with porn. I was 9 or 10 when i had discovered the wonders of my mother's lingerie drawer, especially her slips and bras. As I grew older, I secretly purchased panties and bras from stores that didn't have too many visitors and wore them under my regular clothes to school. Eventually, I got caught, and my interest in these pretty things waned for a while. I purged my entire collection."
"I went off to college and put all of my focus on school and didn't look back. I believed that I would have no desire to cross-dress anymore and wanted to live a new life as myself. Then I finished school moved cities and started living alone. The whole feeling came back. It did not help that it became more accessible cause of online shopping. I started ordering a few things from Amazon, to just have an item to wear when I go on business trips. As I wore them under my clothes, I wanted more, and of course, over the next few months, I had ordered many items that now are downstairs in couple of the boxes."
"Then it became an every weekend ritual. I'm sorry, I should've told you earlier and what I have told you is the entire truth.
"How did Maria find out? "
“I moved cities and lived next to Maria's. Every time she travelled, she asked me to water her plants or put her amazon boxes inside her house. Since I was home in the evenings, I didn't think anyone would notice so I went there dressed and poured water for the plants and put her parcels inside. It excited me to go out dressed even if it was a short walk She saw me on the security camera and rang me up to ask if it was me? She said she didn't mind she just wanted to make sure I wasn't letting strangers into her house.
"Have you been with a guy?"
“No, I'm not gay.”
“Bisexual?”
“Guys just didn't do it for me, even when I got dressed”
Are you sure? Do you want a sex change?
"No, I didn't want to be a woman, I enjoy being a man too much. I love being your man". That made her smile, and I knew I had a chance, "I just like playing dress up sometimes. And yes, there is always going to be a chance that I will want to dress up and I won't lie to you, I never see this going away permanently and I don't really understand why I do it, but yes, I wish with all my heart I did not cross-dress or that it did not excite me the way it does."
“I tried stopping. My compulsion, my need to dress came and went and no matter what I did, it always seemed to come back.”
“I hate it and yet at the same time I love dressing up as a woman. I don’t know what triggers it, sometimes I don’t think about it for months. Sometimes I think about it for days together. When I was younger, I felt extreme guilt, growing up I realized as unnatural as it seems I didn't want to be at war with myself”
"That's why I keep the box," I confessed. "After getting rid of everything eventually I'm back at it buying it all over again. I've always enjoyed dressing, it's just that there are times I find the urge to do it won’t go away."
"Being with you is amazing, and I love every moment. I wouldn't give it up for the world "
Lily gave me an empathetic smile and rubbed my arm. "This must all be so hard for you James. Thank you for telling me everything.
Does anyone else know about your recent dressing habits?"
"No, but I occasionally post censored photos on reddit and delete them after a couple of hours," I answered.
"Oh my.... you like teasing people online. You are a naughty girl, aren't you? Does it excite you?"
“Yes, it does"
"What else did you do?"
"Well, I kind of write fantasy stories."
"What kind?"
During my college years, I found solace in writing stories about my fantasies instead of indulging in crossdressing. It wasn't about acting on those desires; rather, it was a way to live out my desire and contain them, allowing me to navigate through that part of myself without physically expressing it.
"I want to read it sometime. Why are your hands shaking?
"Because some of these stories are very explicit, and things I would never dream of doing. Those are just fantasies, and not something I really want to happen.”
"Well, I also realize that there is some truth in every thought and fantasy. I'm going to read exactly what was on your mind and discover your deepest desires. I would rather that you told me about your fantasies before all this happened or in bed, while we were being intimate with each other."
“What other secrets have you been keeping from me?”
“I like being humiliated.”
She raises here eyebrow. “What do you mean?”
” I like being ordered around. I like being told to get on my knees and be spanked. I have a little anal fetish. I like having my back door stimulated. I want to put on a butt plug and chastity teased mercilessly.”
She raises here eyebrow.
“You see why I am concerned now?”
“Look I promise you I’m not gay. I’m not attracted to men. The whole feeling goes away once i orgasm. I hate myself after. I don't even want to live like a lesbian”
“I fell in love with you and was excited when you agreed to become my girlfriend. I promised I would love you forever and I intend to keep that promise."
"I know love. That is why I'm still here trying to understand this."
"Ok let’s take this one at a time. Will dress up and you show me?"
"Are you sure you want to see me like that?"
"No, but I think I need to, don't you want to show me?" she slipped her hand into mine as we made our way to the boxes that had my female clothes. Lily laughed at how slutty and unpractical the outfits and shoes were.
“I don’t even want to ask why you have a 5-inch stilettoes or a satin thong.”
“Normal clothes don’t interest me; I love the ones that are slutty. I love showing my waxed legs in a tight dress or a mini skirt parked with heels”
She laughs, “Inspiration clearly picked up from porn. Pour me a drink and get ready and come back”. She said as Lily picked the phone to order some Chinese takeout.
I dressed in a maroon halter dress, garter and stockings, five-inch stilettoes and a pink bra and matching panties that were a little lacier than anything any of my girlfriends owned. My silicone inserts to make it seem like I have a little cleavage. I then put on a shoulder length jet black wig; I started applying my makeup, my skills in this area were average. Nevertheless, I exerted my utmost effort to achieve a presentable look. I carefully applied my foundation, eyeliner, blush, and a bold red lipstick. After one final glance in the mirror, with my heart still racing, I summoned the courage to step into the living room.
She gasps
"You actually look nice. I expected a street walker" She smiles. “But this is not bad. Get yourself a drink and sit with me”
I took a sip; I could see my lipstick stain on the whiskey glass. This was exciting me.
“Does this beautiful face have a name?”
“I don’t really…”
”If you like to dress like a girl, you ought to have a girl’s name” she said before I could reply.
“I haven’t thought about it”
“It sounds like fun. What do you think about Sarah, how about I call you Sarah when you are dressed like a girl” she grins
“But...” I explain
The food delivery man rang the bell.
“Answer the door, Sarah” she tells me with an evil look on her face.
“That sounds dangerous” I exclaimed.
“Look in this mirror. What do you see? Can YOU even recognize yourself? All he'll see is a very attractive woman getting food.”
I couldn’t argue, I couldn’t think. I open the door. I got a strange look from him, and I paid him.
"Admit it, It turned you on didn't it"
I shrugged. Lily couldn't stop laughing when she saw my face flushed after he left.
Lily and I dined together.
"I still need time to process this, but as long as it didn’t escalate, I could get used to it". She said as she remained uncertain about my cross-dressing.
"I can live with that" I said and chose not to say anything else.
"No more secrets." Lily reached across the table and took my hand. "Promise me, no more secrets. Can you do that?"
I nodded, taking her hand in mine. "I promise."
Chapter 4
After dinner, I packed everything back in the box and put them back in the garage. I had a bath took off all the makeup. Lily and I crawled into bed and had possibly the best sex we had ever had. It started slowly, with a little cuddling and nuzzling,
" I love you Lily, I don't think I ever knew what it meant to love a woman before, until you."
“I know, you love me” She kissed me again. I move forward to kiss her, each kiss getting more and more passionate, my hand sliding down her side to find the hem of her sleep shirt, making my way gently underneath, softly caressing his hip and side with my fingers, almost a tickle, but not quite.
Lily let out a soft moan as my hand made its way to her breast, she bit her lip and smiled at me as I gave her supple breast a soft squeeze.
“That is very brave of you to expect sex after that”
"Well, there are lots of ways to apologize for things," I smiled back, kissing her on the tip of her nose, and making my way across her cheek around her mouth to her ear, giving the lobe a soft nip with my teeth, before I covered her neck with kisses, sucking lightly, just enough to get a response but not enough to leave a hickey.
I looked down on her beautiful body, "I don't think I've ever seen anyone as beautiful as you," I smiled at her, taking my time to explore as if it were the very first time, one hand massaging and fondling one breast while my mouth kissed and licked the other, biting her nipple gently eliciting the soft moans I knew it would bring, trading off, one for the other until her hands gently pressed on my shoulders, encouraging me to move lower and continue my exploration.
Across her stomach, driving my tongue deep into her navel before I traced a thin wet line down her abdomen to the band of her panties, my god. Her scent was strong. Lily lifted her hips, and I pulled her panties down her legs, bringing them to my face and inhaling deeply as I gazed hungrily at her now naked form.
The longing in her eyes was begging me to keep going, so I started moving up her calf, rubbing my hands over her soft skin as I left kisses up her leg to her knee, when I kissed the back of her knee, a soft tremor ran through her body. My lips went back to her knee, slowly working to the inside of her thigh and sliding up to the prize. I could see her juices dripping.
My hand moved underneath her, drawing a single finger up across her slit. I brought the now dripping opening to my mouth, relishing the full flavour of her juices. I couldn't stand it any longer, I buried my face in her crotch, sucking and nibbling on her clit like a fiend possessed, her hands found the back of my head, holding me in place as the soft tremors that had started when I kissed her knee turned into spasms, her body arching and shaking as pleasure tore through her.
Making my way up across her stomach back to her beautiful breasts, kissing and licking her nipples with the tip of my tongue, nibbling on them, squeezing, and pinching them with my fingers as her fingers massaged my head, urging me up to her waiting mouth while letting me continue to explore and bring small aftershocks of pleasure to her.
Slowly up along her collar bone to her neck, leaving a trail of delicate kisses along her chin to her ear where I nibbled on her lobe and slipped my tongue into her ear, "Oh, James, what are you doing to me?" she moaned.
"Just letting you know I choose you over everything else." I made my way to her lips and buried my tongue deep in her mouth.
She pushed me over on my back and climbed on top of me, taking me deep inside her, riding me hard, chasing her own orgasm "Oh god fuck me" she said, breaking our kiss. "Your cock feels so good, cum now, fill my pussy!" she screamed, losing control as she slammed down harder on my cock. That was all I needed to hear and as her body quivered and her pussy convulsed on my member, it erupted, pumping my seed deep into her pussy. Lily rode me for another few seconds before collapsing on top of me, panting hard as she started to come down from her orgasm. "I love you, too," she whispered in my ear as my softening manhood slowly slipped from her wetness and we fell into a deep sleep nestled in each other's arms.
Chapter 5
We were both late for work the next day. My position at work involves a lot of travelling. Hotel in another town was always my favourite place to dress up. No interruptions. For this upcoming trip, I still wasn't one-hundred percent sure what Lily thought of me dressing, so I was going to have to make this trip with my regular clothes; no panties, no bras, nothing.
This work trip was stressful as it is. Unpredictable weather causing delayed shipment leading to a delay in the overall competition of the project. I was tasked to find alternative transport options and manufactures to source building materials to solve this growing problem.
Lily dropped me off at the airport with a huge kiss and a promise of another when she picked me up in five days, it was going to be a long week, "Behave, and call me every night, I want to know how you are, ok?"
"Of course." I pulled her in for one more kiss, I squeezed her butt and was on my way.
The flight was nothing special. I spent most of it getting up to speed on the meeting I had to conduct. I was going to be talking to and reviewing. Dinner was in the hotel dining room, a quick shower and I unzipped my suitcase to get dressed for bed only to find something I never expected, a card from Lily and the realization that there were no boxer briefs and no socks, in their place, a collection of the prettiest panties, several pairs of stockings, jet black to go with my suits and; there were even matching bras for several of the panties. Three lacy nightgowns and a pair of sexy stilettoes, and a white cocktail short dress. There was a note in the heels, "Just in case you get adventurous," with a huge smiley face and the imprint of Lily's lips in bright red lipstick.
My hands were shaking as I opened the card.
James,
My love, I know you're stressed about this trip. I hope my surprise helps take the edge off just a little.
I love you and your happiness is more important to me than anything. Enjoy yourself, but not too much.
I'll see you when you get home.
Love,
Lily
Before slipping on the red satin night gown, I slipped into bed and dialed Lily's number. "You know I love you to infinity and beyond" I didn't even wait for her to say hello.
"So, you like my surprise?"
"Well, yes, but that has nothing to do with what I just said, and since you brought it up; I have a couple of questions. How? and why?"
"The why is easy, I love you and knew your trip was stressing you out. I thought it would help. The ‘how’ was a little more problematic. I've been planning this ever since you told me about the trip. I may not be completely on board with it, but I thought you deserve a little reward.
“Thank you so much I love this”
‘’I think you should put on the dress and go to the hotel bar” she said amused by my reaction
“I wish, I don’t have that kind of courage” I said laughing
“You may just get free drinks”
“Oh no I don't think I want too just yet”
We talked for a while “Thank you for everything, Lily. I love you more than I can say,".
"I love you too, now get some sleep and I'll talk to you tomorrow." we both waited a few seconds trying to be the last to hang up, "Good night, James," she admonished me, and I finally gave in.
I got up early and took my time getting dressed. Garter and stockings, satin and lace panties with a matching bra and my suit. This excited me with the lace tickling my butt, the nylon massaging my legs, and the garters teasing my thighs, I was ready.
After spending the whole day with the supply chain about alternatives. I went back to the hotel and collapsed into bed exhausted, calling Lily and filling her in on the day, thanking her again for her surprise, and telling her exactly what I had worn under my suit.
"You'll have to show me when you get home," she answered with a soft laugh, "I can hear the difference. It really does help you, doesn't it?"
"It helped in taking the edged off” I paused for a few seconds, letting what she had said sink in. "Would you really like to see me like that? I thought..., well, I think you know what I thought."
I could hear a little reservation in her voice, "But, yes, I think I would love to see how you look in anything you wear. Now get some sleep."
Chapter 6
Lily met me at the airport, when I saw her waiting for me at the luggage claim, wrapping her in my arms, I buried her in passionate kisses while her hands ran up and down my suit to guess what sexy things I was wearing.
“Naughty, naughty Sarah.” she laughs.
When we got home, I let her undress me. Slowly, one piece at a time, my coat hit the floor and then she untied my tie, dropping it on top of the jacket. Slowly, one button at a time, each one separated by a gentle kiss, Lily unbuttoned my shirt, pulling it from my pants, leaving me bare except for the Black lacy Bra, matching satin panties, garter belt, attached stockings I was wearing underneath, and running her hands up over my chest, delicately tracing her fingertips across the lace of my bra, she shuddered as she let out a soft sigh.
"Are you ok with this?" I whispered. She just nodded, running her fingers delicately up the bra straps and slowly down my arms, taking my hands and leading me closer to the bed. My belt was next, Lily breath got faster. I could sense her nervousness, her trepidation, her anxiety as she continued to unwrap my satin and lace clad body. Dropping to her knees, she slowly lowered my trousers to my ankles, helping me step out one foot at a time.
Running her hands up my nylon covered legs, I watched as she licked her lips and tried to catch her breath, her fingers tracing the top of my stockings and then following my garters to my waist, following the satin to the little bow in the center of the garter belt before sliding her hand down between my legs, rubbing my aching cock with her palm as it strained to get free from its chastity prison.
"I wondered what you did with him," she smiled up at me, "Doesn't seem all that comfortable." her smile turned into a grin; I laughed.
"It was until a few minutes ago" I smiled down at her, as I give the keys to her and letting her decide what the next move would be.
"So, he'd like to come out and play?" her hand stroked him again.
"Yes please, or he's going to make a bit of a mess the way you're treating him."
"Well, we can't have that, now, can we?" sliding her hand up and then into my panties, she freed my raging erection from his captivity, kissing him gently as he thrust forward to greet her, receiving a caress from the tip of Lily's tongue along his slit.
Lily started slowly at first, kissing and teasing my cock with her tongue and lips as I stood there in my lingerie doing everything I could to not lose what little control I still had, my body had never been so charged with sexual energy, every breath made the lace of my bra as it moved with my chest more erotic, every flinch, every change amplified the feeling of the delicate fabrics that covered my body. And what Lily was doing to my cock. Her mouth was magic, her hand reinforcing everything it did with just the right squeeze, just the right touch.
"Lily, I can't... I'm going to..." She squeezed the base of my erection and brought me back from the brink.
"Not just yet, I've been fantasizing about this all week," she gave my testicles a little nip with her teeth, sending a shudder through my body which triggered all the wonderful feelings. Lilly undressed me completely and followed that by shoving me on to the bed, and crawling in front of me.
My god I was dying from sensory overload, the pleasure, and then the little touch of pain, the denial of my release, just when I thought I could take no more, she slid a lubed finger down the crack of my ass, teasing. Without warning she shoved it inside me and took my cock all the way down her throat. She moved her head with the same pace as the finger. I gasp and groan, welcoming the new member. She crooks her fingers and hits a sensitive spot inside me, rubbing against it with maddening slowness, intently watching every expression that crosses my face. I can’t look away from her. I want to, but I can’t. She took my full cock inside her mouth matched the pace as her fingers caressing inside me, while her free hand was squeezing my balls.
I bow from the bed, shaking and sweating, loving every hot swipe of her tongue over my cock, though it’s exquisitely, almost painfully sensitive. I'm on the verge, pulling her hair and moaning, until she sinks two fingers inside me.
“You’re the most perfect thing I’ve ever seen in my life,” I moan. She smiles at me
“You want to come like this, baby? She said finger fucking me as I squirm and gasp.
I shudder I felt my orgasm growing. I couldn't hold it any longer.
She felt me near and stopped.
Chapter 7
Lily
He pulls me against his body and places me on his lap and kisses me. I wind my arms up around his shoulders. Cradling me in his arms, he sweeps his tongue against mine. Within seconds, I’m lost to it. My fingers creep into his hair. All that soft, freshly shampooed hair. I tug on it, wanting him even closer. Wanting him to devour me with his mouth. The kiss goes on and on, going from sweet to hungry and back again.
I feel a wild, animalistic urge for him to throw me onto the bed, hold me down, and fuck me. Without thinking I blurted “Will you please fuck me with that amazing cock of yours now? I love having it inside me.”
He presses his thumb against my clit and slowly works his finger in and out, fucking me with it. I shudder, dropping my head against his shoulder and biting my lip so I don’t make a sound. Until he adds another finger. Then I groan. He smiles while dipping his head to latch onto my throat with his hot mouth. He sucks on my neck and finger fucks me while I helplessly grind against his hand.
Rocking his hips into me so his erection is pressed right up against my hip, he kisses a path down my neck to my chest, then licks at my cleavage, dipping his tongue into the cleft between my breasts. When I groan again, he lightly bites down on the swell of one breast. As I watch in dizzy, breathless astonishment, he lazily licks his slick fingers dry, savouring my taste.
Lily swallow and moistens her lips.
“I need to taste every inch of you,” he whispers, his voice dark.
“I want to fuck you and spank you and make you take my cock down your throat. I want you to tell me every filthy thing you want me to do to you.” He pulls his fingers out of me and slides them and down through my soaked folds, spreading the wetness around. When he brushes against my clit, I jerk. He bites my nipple hard. I moan softly
James
I made my way laboriously to her opening, her juices running down. Lapping up her divine offering, I felt another series of shudders run through her as an orgasm followed, her breath heavy with lust, her body slick with the sweat of passion, I tasted it all, my tongue opening her lower lips, my mouth suckling, teasing them as I pulled them deep into my mouth. Eliciting loud moans of eager anticipation as Lily ran her fingers through my hair, urging me to continue pleasuring her, her body shaking with the aftershocks of what I had already done, her soul hungry for what was next.
“I like how you’re flexing your hips to try to get my fingers back inside you.” Lily drops her head back and squeeze her eyes shut.
“Ask me to fuck you. Ask me to make you come. I want to hear it.” Sweeping James fingers back and forth over her throbbing clit, “Tell me you need my cock. Tell me you want me to fuck you. Tell me you’ve been dreaming about it every night and aching for it every day, the way I have.”
Staring into his eyes and breathing hard, Lily whispers, “I want you to fuck me. I want you to kiss me and lick me everywhere. I want your cock, your hands and your mouth and every other part of you. So please make me come now.
You’re fucking perfect, inside and out, you take my breath away.” Lily swallows hard.
Her voice comes out small. “Yes, but you’re strange.”
James drops my forehead to her neck and start softly laughing.
Lying on top of James kisses Lily with a strange sort of desperation he says I don’t have the right words.” “For what?”
“How beautiful you are.”
She smacks me lightly on the back. “Shut up and fuck me.” James kisses her again, deeply but not hard, letting her relax into it. Bending her knee, she slides her leg up against mine and flexes her hips.
Lily
The only thing I know is that the bulge in his underpants is erect and hard, and I want it inside me desperately. But I bite my tongue and keep quiet, letting him go at his own pace. Thumbing over my rigid nipples, he kisses his way down my belly, pausing to bite my hip. Moving lower, he bites my inner thighs, too, one after the other, licking and sucking the flesh where his teeth pressed. It feels so good, I groan. He whispers, “You like that?” “Yes.” “What about this?” He gently bites me between the legs. I hold my breath, stiffening.
He quickly pulls off my panties, then gets right back between my legs, lapping at my folds with his tongue. I groan louder, pulling his hair. The rest of my body goes wild. A violent shiver of pleasure runs all the way through me. My legs open wider.
“God, I need to sink my cock in this.” James groans making a garbled sound of pleasure as he runs his tongue up and down her opening. I pull back the hood on my clit and he flicks his tongue back and forth over it, I moan, long and loud. He slides his thick finger inside me.
“I’m going to fuck your pussy and make you come again.”
“Too much talking!” Lily cries, bucking her hips. “Just do it!”
His lips fasten onto my clit. He sucks, shoving his finger deep inside me. I groan, arching against the mattress, my fingers dug into his hair and my bottom clenched as I grinds helplessly against his mouth. Crying out and pulling his hair, she reaches climax. It rips through her. Her hips thrash and buck through the convulsions, delirious at the feel of his hot lips and tongue licking and sucking her pussy and his finger plunging deep. Her nipples are hard and painful. A bloom of heat flashes over her. Sweat mists her skin.
The moment the convulsions have slowed, and he rises to his knees, and fists his cock in his hand. I stare at it with wide eyes. My hammering heart skips a beat, and again beating even faster. Thick and veined, the shaft juts out proudly from his fist. The crown is fat and red. The slit on top glistens with a drop of wetness. Then he positions himself between my spread thighs and slides the head up and down through my pussy lips, wetting it.
“Fuck me, James. I want it all.” She groans. His grin looks feral. With a single, powerful thrust, he shoves his thick beast deep inside her. Stretching her wide, impaled on his cock, taking every inch of it and clamp her shaking thighs around his waist. He leans down, resting his forearms on either side of her head and fisting his hands into her hair. Then he snaps his hips again, thrusting hard.
Into my ear, he snarls, “I knew you’d feel like heaven.”
He thrusts again. And again. And again. Each time, she feels it go deeper and moans, lost to sensation. Just as Lily was about to come again, he rolls onto his back, taking her with him. Breathing hard and sweating, Lily stares down at him in hazy surprise. He looks up at her with blazing eyes and orders, “Fuck that cock, baby. Ride me and make yourself come.” She almost passes out from excitement. Leaning over, Lily plants her hands on his strong chest and balance herself as she bounces up and down on his thick shaft.
"You feel incredible.” She says seductively as she shuts her eyes and parts her lips.
“You’re perfect. Look at you, these tits.” He reaches up and engulfs her breasts in his big hands, squeezing and fondling them as she rocks back and forth, grinding her clit against his pelvis. He pinches both her nipples at the same time, and her grinding grows more frantic. When he sits up, grabbing me around the waist to steady me as he latches onto her nipple with his wonderful hot mouth, it forces his cock even deeper inside her. She starts to buck and groan, pulling on his hair. Holding her tightly with his arms wrapped around her waist, he thrusts into her with short, hard snaps of his hips as her pussy clenches around his cock. He throbs inside her pulsing and stretching her wide. He bites her nipple, and it pushed her over the edge, and she comes, screaming. Convulsing rhythmically around it, like I’m trying to milk the cum right out of him
“Yes, come inside me, let me feel you come!” Hearing her beg like that unleashes something in him. He was carnal before, but now he’s an absolute animal, snarling like a hungry beast set free from a cage. He flips her onto her back again, throws her legs up so her ankles are hooked over his shoulders, then fucks her hard and fast, leaning over her with locked arms and wild eyes, his teeth bared as he plunges into her.
“Oh God!” He swallows her cries, crushing his mouth to hers and groaning into it as his body shudders and heaves. She felt him throb deep inside her. He jerks, biting her lips. Then he throws his head back and groans at the ceiling as he makes one final hard thrust and empties himself inside Lily.
“He’s beautiful. God, he’s so beautiful like this, sweaty and straining, his entire body clenched. I wish I could take a picture to look at later, so I won’t forget a single detail. “She thinks to herself
Panting, he collapses on top of her. His whole-body trembles. He pauses to catch his breath, then takes Lilys face in his hands and kisses her deeply.
He lifts his chest and pulls her legs down, then settles right back on top of her, keeping his cock seated inside her the entire time. She wraps my arms up around his shoulders.
Completely sated, our marathon run, lingerie spread across the floor of the bedroom, we lay in each other's arms, kissing softly, hands exploring exposed flesh, sharing tender caresses and light tickles, our sweat covered bodies as one, neither of us wanted to move, I wasn't sure I could.
Chapter 8
I woke up before Lilly the next morning. Wore T-shirt and shorts went to the kitchen to make thank you breakfast. I place the hot chocolate and pan cakes on the counter, and I hear lily waltzing in.
"Ohh, that smells soo good" she kissed me
Our fingers interlaced, lost in the simple beauty of the moment until Lily broke the silence, "I thought you said dressing wasn't a sex thing for you," the smile on her face when I came up for air told me she was kidding, but I answered anyway.
"With what you did to me, a clown costume would have been sexual," I grabbed her, pulling her into a huge kiss. She feigned protests not even trying to stop me.
"So, would you like to try it again sometime?" she whispered in my ear, kissing me again. I'm sure the look on my face as she gently pulled her lips from mine was priceless. "That was the hottest thing I have ever done, undressing you, seeing you like that, the garter and stockings, the satin and lace, your hot body underneath, the way you reacted to every little touch and caress, the way your body shook when you exploded
There was no doubt in my mind I was going to do whatever it took to keep Lily in my life, making a note to myself to reduce the time I indulge dressing up. But Lily had other plans.
"You love me, right?"
"You know I do," I smiled at her.
"And that means you trust me, right?"
"One does imply the other?" I raised an eyebrow and gave her a sideways glance.
"Don’t answer my questions with questions.” she laughed and swatted me on the butt.
"Just trust me," she kissed me again, and I didn't get to finish my questions.
Lily and I pulled into the parking lot in front of the Serene Spa and Salon. Go into the salon and ask for Rose, my stylist. I've planned an entire afternoon, as a spa day for you, my darling. You will be here for several hours getting pampered and spoiled. Rose has a list of everything you are to experience today.
"If you want me to know what it feels like to be pampered like a woman, then I'm all in," I turned to kiss her, catching my reflection in the mirror.
Every cross dresser fantasized about two things, seeing what they would look like as a woman, and finding someone that will support them in their dressing. I knew I had the second one in Lily, and now she was giving me the first one.
I went to the receptionist, a young tall girl with perfectly applied makeup, styled hair, and sparkling smile, and said, "I have an appointment with Rose."
"Lovely, I'll let her know you're here. Please have a seat." As I looked around. I never had a spa day and thought it would be fun to be pampered all afternoon. Maybe a massage or a facial, I was wondering what she had planned. I was relaxed and starting to just enjoy the experience.
Rose greeted me and brought me back to a private area.
I sat in her chair observing the room, which was completely designed for women, which made me feel a little out of place. I didn't have a care in the world, and she handed me a glass of wine I sipped on as Rose came back into the room holding a notepad.
Rose smiled and I stared at her as she said hello. "First we have a full body waxing in store for you. Please take off your clothes and lay on the table, I'll be back in a few moments."
After taking all my clothes off I got on the table and covered myself with the disposable thong that was on the table. I had a big smile on my face as Rose came back in and commented, "You seem happy today, and I'm pleased to meet you."
For the next forty minutes, Rose gently applied and removed hot wax over my entire body. I was feeling so relaxed and comfortable that when she got to my private area and applied wax to all my pubic hair, I didn't even resist. I felt the pain as she ripped off the strips of wax, but it didn't bother me enough to complain. She spent some time between my legs making her I was hairless everywhere. When she was done, she rubbed a lavender-scented oil over my entire body.
"Doesn't that lotion smell delicious?" she said as she was going over her work.
"Oh my god, it's amazing. It feels so good."
"I'm sure you'll be back for maintenance to keep you nice and smooth, but right now don't move as I work on your eyebrows, honey."
She took her tweezers and started plucking away. This went on for at least five minutes and I was wondering If there were any eyebrows left. I was there for less than an hour, and when she was done, she handed me a pink robe and matching silky shorts, "Slip into these, honey," and then led me over to the washbasin where I was handed off to another lady who introduced herself as Gloria.
Over the course of the next twenty minutes, Gloria dedicated her skilled hands to lavishing care upon me. Beginning with a thorough cleansing and rejuvenating scalp massage, she then transitioned seamlessly to meticulously grooming my hands and feet, indulging me with both a manicure and a pedicure. As she delicately applied the vibrant red nail lacquer, I couldn't help but admire the dazzling shine it bestowed upon both my hands and feet, revelling in the newfound radiance of my polished nails.
Rose came to get me and asked me to follow her into a changing room
"Well, we are ahead of schedule and that will give me more time to make you perfect. Lily called and She's excited for you and can't wait to see you later this evening. “She said as she handed me a suitcase and left me to it
I eagerly unclasped the suitcase to find a delicate white lace thong and a matching padded bra designed to accentuate my figure, complete with silicone inserts, along with a package of thigh highs and garters. Each piece meticulously chosen to harmonize with the overall aesthetic and elevate the outlook. When I heard Rose’s voice asking me if I needed any help, I realized that several minutes have already passed.
"I'm fine, Rose. I'll be out in a few minutes," I said as I got undressed and inserted the heavy silicone pads into the lace bra. The silicone pads had built-in nipples that would protrude from the fine material of the bra and put me on display. Everything fit perfectly as the bra slipped into place after I adjusted the straps. I stepped into the thong as it tightly covered my chastity cage, which I suppose the keys to is with Lilly. I opened the package of pantyhose and slid them up my freshly waxed legs. They made me shiver with pleasure when I finally had them in place. For some reason, the feeling of wearing stocking reinforced my feminine feelings. I was now excited to see what outfit Lily had selected for me to wear. I was now excited about everything and no longer thinking about what others might think or say.
When I opened the garment bag, I gasped. There inside was an amazing There was a red sexy backless deep V Neck sleeveless dress. Along with sky high pencil stilettoes. It felt magical when I stepped into it and zipped up the side zipper. The skirt fell just above the knee, and flared out, as the material clung to my waist. The thin material of the dress allowed the nipples from the silicone pad to be visible as I moved in different ways. In the suitcase, I found a small purse. I realized that Lilly had picked all the right sizes as I slipped into the heels.
Just at that moment, Rose popped her head through the drapes, "How are we doing in here James? Oh my god! Is that you? This is amazing, you look so good!.”
"This is to complete the look," She said with a gleam of excitement in her eyes. Delicately, she adorned me with some jewellery, each piece adding a touch of elegance to my attire. With precision, she placed the necklace around my neck, ensuring the pink drop-shaped stone rested perfectly against my collarbone, completing the ensemble with finesse and style. She turned fastened a pair of clip-on earring and called out, "Girls, come here, you have to see this."
That made me nervous and embarrassed as the girls stepped into Rose’s area and gasped when they looked at me.
"Holy…., she's amazing. Looking like this, nobody would ever believe that you were ever anything else but this pretty girl. Come with us to the full-length mirror and see for yourself."
Rose took me by the hand and led me out to the main area where there were several mirrors. When I saw myself, I understood why they were making such a fuss. With my new feminine hairstyle, alluring jewellery, glamour makeup, painted nails, high heels, and the amazing sexy dress, I realized that Rose had transformed me into an extremely attractive girl of my dreams.
"Wow, I never knew I could look like this. Thank you Rose, for today and I have to admit, I love it. Thank you, everybody," I said realizing that I just admitted to everyone that I was excited to be transformed into a beautiful girl and thanked them for doing so. I was not in my normal state of mind, but it was too late to take anything back. I just continued to admire the girl in the mirror as I turned and looked at myself in every position.
"James, we're so happy you like how you turned out, and we hope you come back whenever Sarah is feeling adventurous."
Chapter 9
It was now after 6 pm and they were about to close for the day, so it was time for me to leave. Lily messaged me the name of the restaurant I had to meet her at. I then realized that I had to call an Uber and fumbled for my phone. I giggled to myself as I tried to use the Uber App with my red nails. I wasn't used to having nails bright red.
A few minutes later my ride pulled up in front of the salon and I realized I was about to go out as Sarah. Scared but feeling confident I held my purse and walked comfortably in my heels out to the car. I would be presenting Sarah to my Girlfriend for the first time in public. I didn't know what to expect but realized that since she planned everything, I had nothing to be worried about. Inside I was laughing about the special treatment for a pretty girl, but I took advantage of his offer. The uber driver opened the door.
"Thank you again” I said smiling
"My pleasure Miss. Anytime!"
I was now standing at very nicely light romantic Italian restaurant and took a deep breath as I walked inside. The hostess at the restaurant showed me to a table while I waited for lily to arrive.
"My lord, is that really you? I mean, you're beautiful. I mean you're a girl. I mean you look like a pretty girl. I had no idea!" she said with a big grin and sat across me. The look on her face said it all. Even though she arranged for my transformation, it was obvious she didn't expect the results to be so dramatic.
"I expected you to look more like a guy or maybe a not so pretty girl, but nothing like this. I don't believe anyone would mistake you for a guy, the way you look."
"I have to admit that I'm shocked at how I look, and I can't get over what a good job they did back at the salon. I love this but also, I'm so embarrassed. I replied
"No, don't be. I think you're amazing and I'm happy I get to meet her and be with you this way."
"Thanks, Lily, I wasn't sure about all this but if you're OK with how this turned out, then I'm happy. To be honest and something I would never admit, I've always dreamed of meeting you this way, and you've made one of my dreams come true."
"Oh, you're welcome, Princess. You can also count on many more of your dreams coming true, I can assure you of that."
We sat there for a while just talking about my salon and how I felt about everything. I started to relax and feel more comfortable around in public.
When lily said "I went to Maria to ask more details about your dressing. She gave me the idea and it's only fair to her to see you like that, can we take a selfie?"
I nodded. After taking the selfie, we ordered and ate and talked, with her pestering me with questions about how it felt and how was I enjoying myself. It was magic. she reached into her bag and pulled out a box.
"Happy birthday James" she said as she placed a box, sealed with a ribbon, in the middle of the restaurant table.
I smiled. Now I really smiled.
"Can I open the present?", I said.
"Go ahead but be careful."
I slowly undid the ribbon and opened the top of the box, expecting to find something fragile inside, but I quickly realized that by "be careful" she really meant "be discreet." Inside was a lube and a black object whose flared base and interesting curves made it clear that it was a prostate massager.
Suddenly the prostate massager started vibrating inside the box. I briefly panicked as I wondered how to turn it off before somebody noticed but then it stopped, and I saw that Lily was holding a small black device. She pressed the button on it a couple more times and the massager turned on and off again. She smiled in a way that was somehow simultaneously sexy and devilish, waited a beat, and then said "Aren't you going to try on your next birthday present? You've got to see if it fits!"
I thought the idea was hot and said laughing, "I'm pretty sure it's going to fit perfectly."
"You're going to have to use the women's bathroom. Don't worry, just act like you belong there and no one will know the difference. And EVERY girl ALWAYS checks her makeup before leaving the bathroom, so if you want to fit in, make sure you do too." Lily whispered silently
Following her instruction, I put the vibrator and lube into my handbag headed to the restaurant bathroom. Inserting a prostate massager in the stall of a public bathroom is a challenging task and dressed like a woman in public made it even more complex. There's no counter to put things on, there's the constant fear of dropping things on the floor or in the toilet, and there's the need to do the whole process in silence.
I managed to lube the prostate massager, insert it into my ass, put the lube in my purse, and my panties pulled back up without incident or excessive noise The sensation of the toy was peculiar, yet strangely enjoyable. It felt comfortable. I redid my lipstick. Glancing in the mirror, I walked back to the table with without falling to the floor in my high heels. I didn't even make it back to the table before it started vibrating. Lily grinned at me as I sat down - the toy was pushed in deeper than it had been. The vibrations were intense- dampened by being surrounded by my flesh.
We'd already had dinner, but Lily insisted on lingering over dessert and another round of drinks, occasionally starting up the vibrations. She'd do it when I was in the middle of a sentence, to see if she could trip me up. Finally, she called for the bill and after settling with a generous tip we headed for the exit. She made a brief stop in the restroom and then we headed out.
Chapter 10
She wanted to test my tolerance for humiliation, and suggested a trip to the mall. We took a route through a small park and when we passed through a secluded area Lily pulled me off the path and up to a tree. She turned on the vibrations and then reached around and pushed on the end of the massager through my dress, wiggling it around as it vibrated inside me. I groaned at the sensations and my dick hardened inside my chastity cage. She stroked my cage with her other hand, and I groaned even more.
Lily then turned me around, pressed me against the tree, and then pushed her crotch against my ass, while reaching around to rub my balls. I felt something firm pressing against my ass.
"What do you have..." I started saying as I reached behind me to feel what was poking into my backside. I felt the unmistakable shape of a strap on dildo beneath her dress. "When did you put this one?" - I knew it hadn't been there all night.
"I've been wearing the harness all night. I had the dildo in my purse, and I slipped it into the harness in the bathroom as we were leaving. I guess I successfully hid the bulge in my dress with my purse. Now you know what the rest of your birthday present is."
The still-vibrating prostate massager plus the dildo pressing the massager into my ass plus the anticipation of what was going to happen tonight had turned my hardening dick into a rock-hard cock that was trying to break out of my cage.
We stopped near a streetlight, and she said let me take some more photos, Strut and sway your ass as much as possible. As we continued our walk to the mall, we stopped a few more times for her to rub my balls, or me to rub her dick, or her to push the prostate massager deeper into my ass.
Once we reached the mall, she held my hand and we walked into a women's clothing store. With her free hand playing with the remote. I had a difficult time maintaining a calm face. As soon as we entered a women’s clothing store, we were approached by a sales assistant
"Are you looking for anything specific. Erm, miss...?" A young saleswoman, probably in her early twenties approached us. The store was empty
"Sarah " I said nervously.
"Nice to meet you, Sarah. I’m Emma. Anything I can help you find this evening?" She Repeated"
" Not really. We just saw the store from across the........."
"Oh Yes! Sarah here recently lost some weight and She’s a crossdresser. She's in need of some outfit for nights out on the town." Lily interjected.
My face went flush and I could only hope the makeup was working at hiding some of the redness. I could feel the young woman's eyes working me over, examining me from head to toe. Lily had a wicked smile on her face as she knew I didn't like the close attention this young woman was giving me.
"Well, I would've never known! You certainly don't look like you were ever out of shape!" She exclaimed. I wasn't sure if she was being honest and couldn't tell something was off or if she just smelled a big sale and was willing to play along.
"Let's start with every woman's best friend, a little black dress." With that she led us over to a rack and started picking through them. "You're about a size 8 I'm guessing?"
"I'm not quite sure, I haven't really tried much. Im still experimenting. Lily made me come out to buy correct fitting outfits." I lied. Lily's face broke into a smirk, and I could sense her struggle to stifle a giggle over the harmless lie. ‘” He’s a new woman, Let’s give him a taste of the best and worst of what a woman goes through. The sexiest of clothing and something that will make men definitely want to catcall or ogle creepily shall we?.
"How very exciting. I will be glad to help. Well, you can start with an 8 and we'll go from there. Here, let's see how this fits you. Come this way."
She led me to a changing room and sent me inside. I disrobed in the privacy of the change room and proceeded to slip in to the dress. It was a tight-fitting dress with a halter top that left my back wide open, closing in again just above my hips. In the front between the chest there was a keyhole, exposing a bit of my bra. The bottom flared out and fell just around my mid-thigh, exposing the tops of my stockings and showing a bit of the garter straps.
Once I was changed, I stepped out of the change room. Lily and Emma examined me closely.
The material was fairly tight fitting and the adhesive on the breast forms was strong, but without a back to the dress to support the forms and hold them tight, I was nervous. Next, I removed my stockings and garter and adjusted the dress. I spun in the mirror and could feel the unsupported weight of the forms tugging at the skin on my chest. I wore the same stilettoes from the morning, Lily handed me a pair of gorgeous black 4" heeled shoes. I kicked off my stilettoes and slipped my feet into them.
After deciding the dress was a good fit, Lily and Emma paraded me around in even more outfits. Finally buying a little back dress, a red dress, a dark blue Cocktail dress, a white Sun dress. I had never dreamed I'd be in a women's clothing store having trying out clothes. This was wild even for me. They also had me try on different shoes to match each outfit.
"Well, Sarah also needs new bras but we're not sure of the proper size. Could you take her measurements?"
"Certainly. Right this way." Jess replied. I couldn't believe Lily just asked this stranger to measure my chest.
She led me into a change room. After she pulled the door closed, she grabbed a measuring tape and stood there, looking at me.
"Well, you have to take your dress off. I can't get a proper measurement over you clothing." The saleswoman said.
"I can't..." I started to say, but was cut off by Emma.
She took my hand and said “Look Lily told me. I won’t judge you. She came in earlier to ask permission if she can bring her husband. I told her to come with you just before closing. The store will be empty. Don't worry about a thing. We get men in here all the time buying women's lingerie for themselves some try to hide it but it's pretty obvious, and some are brave enough to get ask for a bra fitting. And besides, I never would have guessed you weren't a genetic woman. Your secret is safe with me”.
“You are really good at you job. The things you say makes me want to only shop at your store” I laugher
“Now off with your top and let's get some measurements." She said not wanting to confirm or deny if the compliment wat true
I removed my dress and hung it on a hook.
"Bra too!" The woman said, "We need to know what your measurements are next to your skin."
I removed my bra and put it on another hook. Emma leaned in and wrapped the tape around my chest, just under the forms. She commended me on how well the skin tones matched and how well it was blended in. Next, she wrapped the tape around my bust, right across the fake nipples.
"It looks like you're a 36-C cup with the breast forms and 34 C without them and a M size panties. Wait here and I'll go get some different models to try."
Soon Emma came back with an array of different styles and colours. She helped me into the first one and did up the clasp behind my back before adjusting the shoulder straps. I was shocked at how much more comfortable it was then the ones I had been wearing.
She helped me pick 3 bra and panty sets so I would have one for any occasion. Lily paid for my new collection, saying it was her treat. The saleswoman, with a wink, handed me her card and said, ‘Anytime you need more shopping therapy, just ask for me—I’m the owner. And if you prefer a private spree, after-hours visits are our little secret!’ “She put her hand in mine, and we walked to the basement car park. She sat in the driver’s seat and lifted her dress, revealing the dildo she'd worn. "Suck it" she ordered.
I was so fired up that I was willing to do anything. I knelt and licked the head of her fake cock, then kissed along the sides.
"Stop teasing and suck it" she whispered, I put my lips back around the head and started sliding them down the shaft. The dildo was about six inches long and stiff, so it hit the back of my mouth quickly.
She grabbed my head and started controlling the tempo. With her hips driving the toy into my mouth my gag reflex is being triggered on every thrust. It was a bit uncomfortable, but sexy as hell. I put my hands by my side and let her fully control the face fuck.
After a couple of minutes, she abruptly pulled the strap on out of my mouth, dropped her dress over it.
"Somebody is coming" she whispered. The close call reminded us that it was time to go. It was time to get home. It was time to fuck.
Chapter 11
When we got home, we wasted no time going to the bedroom. "Get ready" she ordered, and she took her dress off. To reveal leather, black Basque with red trim and leather harness with a dildo sticking out. It clung tightly to her body, showing espousing significant amount of cleavage. My jaws dropped. I took my dress off. I was now in my White lace bra and panties with the garters and heels.
She lay down on the bed on her back, cock pointing straight up, and said "Come here and Show me how much you want it." I knelt between her legs and the dildo slip between my lips. As I started thrusting in and out.
She pushed me on my back reached one hand between my legs and started tipping the prostate massager back and forth. It was constantly vibrating as it alternated between pressing firmly against my prostate and moving slightly away.
"Hold on a second" she said, and as I stopped and spread my legs, she slowly pulled the prostate massager out of my ass. With it dropped onto a nearby towel she quickly slid a couple of lubed fingers into my asshole. After a few minutes of this she pulled her fingers out for a moment and then thrust them back in. It felt tighter. She briefly let go of my cock to add more lube, then gripped my cock again as I continued using my hips to fuck the combined tunnel of her hand and her mouth.
A few minutes later she pulled her fingers out again, she took the lube that was pooled around my ass, and then slowly pushed them back in. I groaned as she pushed another finger inside. I started thrusting faster and I desperately wanted release - to shoot me cum in her mouth or all over her breasts. But that wasn't the plan for tonight and she wasn't going to let me ruin her plan.
She pushed my hips away and my cock out of her mouth, and then slowly pulled her fingers out of my stretched ass.
“Fuck me... stop being a tease” He groans. Her laughter is low and sultry as she slides her wet finger over my yearning opening, teasing me mercilessly.
"Patience love"
Inserting another finger, He takes a sharp breath. For a moment she releases his shaft to put a hand on his chest, pulling him up to a position much closer to standing so she can kiss the back of his neck reassuringly. Without pause she continues the steady in-out with her fingers.
She pulls both fingers out of him and reach for the bottle again and pours more lube to his opening. Making sure his hole is lubricated well. She firmly maintains her grasp on his manhood as she squeezes a bit of lube onto her strap on.
Once it's properly coated, she smiles and says,” Are you ready for me to take your cherry” She teased
“Yes” I moaned
"Beg for it, slut." She ordered.
"Please fuck me " I begged weakly.
"Louder! tell me what you want." Lily slapped his ass hard.
"Please fuck me and take my cherry.!" He begged again, louder.
“Bend over” She slaps his ass again
James walks to the bed and complies, hands firmly resting on the sheets, face turned away from her. She lifts his dress, throwing the skirt up to reveal the lacy lingerie. She runs her hands along the stockings, up past the portion of exposed, newly waxed legs, and to the waistband of his panties. In a swift motion Lily pull his panties to his feet, and her hands return to rest upon his ass.
She grabbed the tube of lube and was started stroking her strap-on - her cock. "Now reach back and spread your cheeks for me", she said. It's an odd feeling to be putting my forbidden hole on display for my girlfriend. I spread my butt cheeks and was rewarded with her light gasp. I felt so feminine, and she said "That's so hot. Your ass looks very fuckable."
She squeezes a bit onto the crack of his ass, watching it drip down to his hole. He quivers as she returns her fingers to his ass begin to caress its rosy entrance. She then used tips of two fingers to push the lube into his yearning hole. To help him relax, she reaches around to stroke his member with her other hand. She pushes the tip of one finger into him. A gasp escapes him, and she continue working her fingers, both inside of him and on his manhood.
She moves into position and carefully thrust in.
The first push of her hips only gets an inch or two into him, despite the warm-up with her fingers. She slowly slides in deeper. He moans and grips the sheets, glancing back at her urging her to not stop. She offers him a reassuring smile- and then pushed the last inch of the shaft inside him.
Small noises continue to escape his lips from time to time as she pumps his shaft and thrust into his ass in coordinated, steady motions. Minutes pass, she sees the sweet twitch of one leg, accompanied moments afterwards by a fiercer grip on the sheets and heavier breathing.
“Get on top” she said. As she pulled the dildo out of me and got on her back.
With her hands squeezing her breasts and rubbing over her sensitive nipples I started to lower myself onto the dildo. Eventually one of my soft pushes down met virtually no resistance and suddenly the head went past my anal sphincter and several inches of artificial penis was sliding into my body. I groaned with the feeling of fullness and smiled at the sense of accomplishment.
Once the muscles got used to whole thing inside my body, I just kept rocking up and down, enjoying the pressure on my prostate, and the rubbing against the sensitive nerves of my now glistening rosebud. Occasionally she would lightly press her hips up, but mostly she let me set the pace. I alternate between lusty stares at her body and face and closing my eyes to concentrate on the sensations inside me.
She then pressed down on the cock and thrust back and forth fucking my ass cheeks. I love having my buttocks rubbed it felt so good.
"Please", I said. "Can we finish with me on my back?"
"Of course,", she said, as she slowly pulled her dildo out of my gaping hole.
I get on my back with my hips at the edge of the bed and put a couple of pillows underneath them. Lily took her position between my legs and put my ankles on her shoulders.
She put some more lube on the strap on and without any delay pressed it against my gaping hole and then pushed it in. She stroked my shaft smoothly for a while, and I closed my eyes to concentrate on the feelings. Lily took that as her cue to turn on the vibrator inside the strap on. With my hands on her breast, her vibrating cock buried stretching and massaging my prostate. The view in the mirror of all the action overwhelming me with sexuality.
She reaches with her free hand and wraps her hand around my hardened length. Stroking in time with her thrusts, she ensures that every movement of the dildo coincides with a stroke of my shaft.
She increases the pressure on my prostate, hitting the exact spot that makes me shudder with delight. Her hand on my cock becomes more insistent, pumping faster. Smiling wickedly, she realizes I’m on the verge of climax she redoubles her efforts, plunging deeper and faster than ever before. With a predatory gleam in her eye, she continues to stroke my aching member. Feeling the telltale signs of my impending release, she whispers into my ear, "Cum for me, Sarah. Let me hear you moan while you cum with my cock in your ass like a dirty little slut. You're my dirty little slut and I want you to cum for me."".
Lily cupped my balls with one hand, and my balls tightened up. My climax tears through my body, coating her hand in thick ropes of semen. With the strength of the ejaculation together with the angle of my cock and the elevation from the pillows a stream of cum landed perfectly on my face. The second shot landed on my chest, with the next few pooling in my bellybutton.
I closed my eyes and revelled in the sensations of a great orgasm. Lily leaned forwards and rubbed her chest against mine, using her breasts to smear semen. She brought her breasts close to my face and I licked my cum off her breasts. Then she slowly traced my lips with the cum covered finger. I parted my lips to let her enter my mouth.
“Good girl. Clean every drop of your seed from my finger.” She exclaims as she watches with amusement as I eagerly lap up my own release, savouring the taste of my submission. She withdraws the now-clean fingers. She grins mischievously she pulled the dildo out of my glistening hole, her fingers already beginning to undo the laces of her Basque, baring a tantalizing glimpse of her breasts. Smiling indulgently, she runs her fingers through my hair. and headed to the shower.
Chapter 12
Revelling in the post orgasm joy I couldn't move for a few minutes and then walked to the shower on wobbly legs to join Lily. Lily helped me take off my dress, lingerie and clean my makeup off when we got to the shower, promising to teach me how to do it myself.
We washed the lube and semen off each other's bodies, with her paying particular attention to my ass. Finally, we dried off and climbed into bed, to sleep the deep sleep of the sexually satiated. And telling me to leave my forms in as she handed me a baby blue satin nightgown that matched her soft pink one.
"Thanks. That was amazing."
"You're welcome and Happy birthday." She exclaimed
"Marry me" I blurted
"I don't know, I do love you, but what about this girlfriend of yours, this Sarah,"
I laughed "I only ask a week in an entire year to live as my girl self"
She leans down and kisses me deeply, her tongue dancing with mine. Chuckles softly and pulls away, her lips still tinged with the remnants of my kiss. Gazing into my eyes, she speaks with a hint of mischief. "I don't mind even if it's a couple of weeks in a year, if you can fuck me with your thick cock like man in heat and bring me to orgasm."
“Just imagine what else I could do to you, sweetling”. She laughs, her hands sliding down her curves as she slips out of the leather corset, letting it fall to the floor. The lacey fabric pools around her feet like a discarded skin, exposing her bare torso.
I look at her amazed with her naked body on display.
She blushes faintly at the attention, her eyes sparkling with excitement. She takes a step towards the tub, I follow her, closing the distance between us. Leaning in, she whispers in my ear. You'll get to see so much more if you prove yourself worthy. And she gets into the tub.
I bring my lips to her swollen breasts. As she shivers slightly at the touch of my lips, her nipples hardening in anticipation. She tilts her head back slightly, allowing me access to the soft flesh of her breast.
A soft sigh escapes her lips as she feels my tongue circling her nipples, the warmth of my breath heightening her desire. She closes her eyes, basking in the sensation of my attentive ministrations. My other free hand squeezes her breast.
Letting out a series of small moans as I suckle at her breast, her fingers threading through my hair, holding me close. Stops breathing momentarily, then lets out a sharp intake of breath as I brush my fingers over her sensitive clit. She arches her back, pushing her breast further into my mouth, begging for more. I gently stroke her clit. As I move my lips to touch hers. She closes her eyes and melds her lips with mine, the kiss deep and passionate. Her mouth conveying a primal need that matches my own, she tastes of lust. As I get ready to fuck her once more.