My Very First Time

NSFW - NSFS Welcome to the tumblr library of first time sexual encounters. Everyone's first time is different; romantic, awkward, special, perhaps painful. Regardless of your circumstances, your story is unique and should be shared as part of the human experience. My deepest thanks to all willing to share their stories. You can be identified with a link to your tumblr or you can be anonymous. your choice. Because of the sensitive nature of the subject matter and occasional adult images, no one under 18 is allowed. But when you are of age, come and tell us your story.

[my-very-first-time]

Tree Fort

My first time was pretty young. I was about 10 years old. It all started with the tree fort. The older boys in my neighborhood had this cool tree fort down the edge of the woods. Us younger guys were forbidden to go anywhere near it. Of course, that made us want to go in it more, but we were afraid we’d get our asses kicked if we went near it. One day , one of the older boys was in the tree fort alone and he let me come up. I was so excited to see the magical interior of the tree fort and when I got inside it was… empty. Just a small room with old carpet on the floor. It was cool in my young mind, but it wasn’t this magical place I had dreamed it was. The only thing in the place was an ok beaten up cardboard box over in the corner.

This older boy, I’ll call him Scott, asked if I wanted to see what he had. He opened the box and it was filled with Playboy magazines. I had never seen one before, never really seen anyone naked before. He starts showing me all the naked women and my eyes were popping seeing all the big titties and asses and pussies. He started oohing and moaning about what he wanted to do that pussy. I musta had some look on my face because I had no idea what he was talking about.

(No, I didn’t get “the talk” yet. My parents? That was NEVER gonna happen). Anyways, he could tell I didn’t know what he was talking about.

[my-very-first-time]

Lily’s Story

(Follow her excellent blog here)

My best friend in high school was my introduction into the world of sex. I was super religious, and I was told I needed to wait until after I got married to have sex at all. I wasn’t even allowed to have boyfriends or even boys over at my house.s Story

I spent a lot of time with Megan and she was always the most fun to hang out with. She kept telling me how good sex was and how I should break the rules my parent set just this for just this one thing. I didn’t even know How to break the rule, as I couldn’t get any boys into my room, and I didn’t think it was a good idea to go to a boys bedroom, as I was super paranoid they’d steal my clothes or something. (I always worry about stupid things).

Anyways, Megan suggesting me using her bedroom, and I always said no thanks, but I was too shy to “seduce” a guy into my friends bedroom. This happened throughout high school.

She eventually talked me into something though. She said her boyfriend was bugging her about doing a threesome, but she didn’t want to do it. He was whittling away at her, saying pretty much the same stuff she was saying to me about having sex. She said that she still wasn’t sure if she wanted to, but if she was going to, she thought that that might be a way to “cure” me of my virginity.

She hatched a plan, which I thought was totally bonkers, but I ended up going along with it. She suggested a way that would allow me to back out of it if I didn’t feel like doing it, which is why I said yes at all. The idea of having sex with her boyfriend was strange to me, but the thought of watching my best friend have sex with him wasn’t nearly as bad.

I would hide in her closet, and they would have sex, If I felt like joining them, I could exit the closet, and just join in. She made it seem so simple. Like it was something she’d do any day of the week. (She had a closet with the old school vented doors.) I’d watch through the slats, and if I felt too uncomfortable, I’d just stay in there and “enjoy the view”.

It took some courage, but I said I would do it. At least the closet part.

The day of the plan, Megan and I were waiting for her Michael (her boyfriend) to come over, and she helped me prepare the closet so it’d be comfortable. I couldn’t help giggling, as it felt like espionage… I felt like the James Bond of voyeurism. She talked to me about it, and told me a story of one of the last times he took her on a date. Dinner and a movie, and the choice of both was romantic, so she had dropped down in front of him in the theater and given him a blowjob. She said that was one of her favorite dates. I blushed, I’m sure, and I asked about how it felt. She told me she wasn’t going to say, but if I wanted to know, I could find out tonight.

Anyways, Michael was pulling up in his car outside, and told me to hide for a few minutes, but after they left for their date I could use her computer. She said that she left a few links for me on her desktop. Michael came and picked her up and they went to dinner, while I waited their return. I was super nervous, I thought about ditching and going home right there, but I was too tempted to at least watch them.

I sat there for a few minutes, just waiting, but got bored so I went to the computer and opened the link “for Lily”. It was a link straight to a video of a girl giving a blowjob. I was intrigued, and sat there watching while touching myself. I watched video after video, transfixed, and almost missed the car pulling into the driveway. I nearly flipped out when the computer wouldn’t shut the window down very fast, and rushed into the closet just in time to shut the door quietly, and hear the bedroom door push open quickly.

Megan and Michael were almost rushing to the bed, it was obvious how much he wanted her right then. He pushed her down onto the bed, and started stripping himself down and told her to strip. He sounded almost forceful, and she apparently found that as hot as I did. As he stripped his shirt off, I found out he was more built than I thought and had a very muscular chest.

He tossed the shirt to the floor right in front of the closet, and started undoing his belt, and as I watched I noticed he had a very pronounced bulge in his jeans. I couldn’t tear my eyes off of it.

The button came undone, and then the zipper, and he slid his jeans to the floor. His underwear were pressing his bulge to his body in quite a sexy way, and I couldn’t help but slip my hand down between my legs again. He was definitely sexy.

As he sat there, hands on hips, looking smug, I looked over at her, and noticed that she had stripped down to her panties and bra, and though I didn’t know it before this, I found out I was bisexual. She was every bit as hot as him, with toned abs, lean muscles, and loved the shape of her breasts squeezed together in that bra. I then noticed I was still stroking my clitoris gently, and the thought that I was already doing something quite against my parents wishes turned me on immensely.

Then he grinned, and told her that if she was not going to remove it all, he was. He jumped up on the bed in front of her, grabbed ahold of her panties and roughly yanked them down her legs. That was the first I had ever seen a shaved vagina, and the sight had me transfixed. As he was pulling them down, she was pulling at her bra, almost desperately (I hate how they all seem to have a slightly different mechanism for attachment, and it frustrates me when I am trying to get one off after a long day with it irritating my breasts so much, so I can empathize.)

Anyways, soon she had her beautiful breasts in her hands, and he had her lower lips between his fingers, massaging gently on the outside of her vagina.

I was having such a hard time resisting the urge to moan, and just as hard of a time preventing my eyes from shutting with the intense feelings coming from where my fingers nestled.

I bit my lip to prevent the moan, and watched intently as he slowly pressed one, then two fingers into her moist passage. He was driving her wild. He was driving me wild too.

He soon joined his tongue where his fingers were, and her loud moans went dead silent. At first, I was worried he was hurting her, and then I saw her hands clenching the bedsheets, and her head tilted back in obvious joy. I couldn’t help but admire their beautiful bodies. If my father only saw me then. He would have disowned me.

He kept that up for a few minutes and then apparently stopped as she asked him why. He said that he couldn’t wait any more and he pulled back and stood up at the foot of the bed. He got a giant grin and pushed his shorts down quickly, His penis sprang to attention, and I strangled a gasp, as it was much bigger than it had looked in his shorts. (In retrospect, it was probably about 7 inches, slightly thick, but this was a fairly new sight at the time, and it was bigger than the ones in the videos.)

She slid down the bed, and dropped off the end, onto her knees, but he said not yet, he wanted something else. He stood her up and turned her away from him. He shoved her somewhat roughly, and she dropped onto the end of the bed chest first, leaving her in the doggy position. He then shoved his penis inside of her, and this made her scream out. Again, I worried it hurt her, but she just kept saying yes, yes, yes… I was so worked up at the time, I gasped out loud a few times, moaning as I pressed my fingers inside me over and over.

They didn’t notice though, as she was being much much louder than I was. He was thrusting into her fast and hard, and I just felt immense envy, and begun to see why I might be missing out. This was the hottest thing I’d ever seen.

Shortly afterwards, he pulled out of her, and flipped her over on the bed. Her face was red, but she had a look of such joy on her face. Her started kissing up her leg, stopping briefly on her lower lips, kissing there, then belly, then breasts, taking care to kiss each beautiful nipple, then up to her neck, and as he kissed her neck, her face turned towards the closet door, and she winked at me, and mouthed what looked like “oh my god”. She then pushed him up off of her, and he fell down onto the bed next to her, and she climbed on top of him, gently sliding onto his member. She began to lift and drop over and over, and this was obviously driving him wild as he was moaning her name.

Their position was hard to see from my position though, and I stood up, trying to get a better view. Once I was standing though, I couldn’t touch myself the way I wanted to. Frustrated and decided, I pushed the door open and strode into the room before I could change my mind. I walked three steps in total determination, and then froze… what was I doing? They still didn’t seem to see me, so I started to turn around, and walk quickly back to the closet when I heard Michael’s voice say “So, you were watching this whole time hmm?”

I turned beet red, I know it. I froze in place, still without turning around. I couldn’t face him like this. I was so mortified.

“You look pretty good from this direction too, so I don’t mind”… Had he really said that? I turned around, greeted with the sight of her still gyrating her hips on his. Him, head in his hands leaning back, looking relaxed as possible.

“Megan said she had finally decided to have a threesome with me, but wanted it to be a surprise when it happened, is this it?”

I blushed yet again, trying to stammer a response. “I don’t know” Sounding as unsure as I felt.

Megan looked over at me. “There is no pressure to do it. You can just watch if you want to.” She pointed at the chair she had in her room. “But haven’t I shown how good it is?”

I nodded, biting my lip. If I was ever ready, it was now.

“I… I want to. I’m just nervous.” The words could not explain how nervous I was.

Michael looked at me, still pressing his hip up towards Megan, giving me an almost seductive look. No, not almost. It Was a seductive look. He winked at me, and then thrust upwards suddenly, making Megan cry out and tilt her head.

Michael looked at me again. “Lily, there is no need to be shy. You can take this at any pace you need to. You can come up on the bed, and I won’t touch you until you say I can. You can touch us whenever though, and please do.”

Getting up some nerve, I looked at the chair, then the bed. I decided to come closer to the bed to get a better look. I sat carefully on the edge of the bed, so I could see, but still touch myself. From where I was, I could lean and see from in front or behind Megan, and seeing her impaled on his penis was enough to make me drive a finger back into myself suddenly. I laid down, so I can put my head just by his knees, and watch as Megan slid up and down on his shaft, which was obviously slick with his juices.

I watched for what was probably 8-10 minutes. “Remember, you can touch us any time you like. I’d love to feel your hands on my balls or shaft. I’d love to feel that mouth or pussy on my shaft for that matter.” I remember his usage of the word pussy making me almost cringe, as I knew my parents would hate it if I used that word. It was super hot though. Seeing him be so open.

Their thrusting motions were driving me insane and I again gathered up the courage. Slowly, tentatively, I ran my hand up his leg, and beneath my best friend. I carefully cupped his balls, and he moaned. Megan was still sliding up and down on his penis and her vagina and butt pressed against the back of my hand briefly and he moaned again. I slid my hand up his balls to his shaft, and felt my friends slick juices coating that man meat. She slid down again, this time feeling her clit press against my hand, and I heard her moan.

They almost said in unison: “That feels so good”. They did this for a few minutes with me exploring both their bodies slowly, touching them here and there, all while still finding time to touch myself.

Soon, Megan said she was tired, and asked if I wanted a turn. I said I wasn’t sure if I was ready, but maybe soon. She climbed up off of his shaft, leaving me about a foot away, starting at the glistening erection. She moved over on the bed, and asked “Can I touch you Lily?” I looked down at myself, and over at Michael, and back at Megan. I nodded slowly, biting my lip.

“Lily, you look so sexy doing that.” Michael said. Megan slid around behind me and sat right behind me, massaging my shoulders lightly. “Go ahead, touch it girl. Get it.” I had to laugh a little and how nonchalant she sounded.

I was starting to relax, and reached forward, and slowly stroked Michaels shaft. Megan slid her hands just under my shirt, running them up my back, further relaxing me. This whole time, Michael just sat there being patient while my inexpert hands played with his toy.

Megan began lifting my shirt over my head then, and I had to let go momentarily. It came off, and my first instinct was to cover my chest. Megan giggled loudly at this. “You’re touching his cock, and now covering up all modestly. Come on Lily, you’re going to be fine”.

I felt more confident at that. I leaned back over towards Michael, and ran my hand over his shaft slightly. I felt it firm up a little, getting more lively. “He likes you!” said Michael.

I felt Megans hand on my bra, helping me remove it, and then I sat there in my jeans and panties. I leaned forwards and slightly licked the head of Michaels shaft. He groaned and slightly thrust upwards. “Michael, take it slowly, she’s a virgin” Megan said, teasing me. He knew that already.

She ran her hands down my chest, lightly pinching my nipples, then moving down my belly and into my panties. “Ooo, you’re pussy is so wet girl.” She pushed a finger into me and I almost orgasmed right there.

I leaned forwards, allowing the head of Michaels penis to slide past my lips, moaning with Megan’s attentive touches. I soon was trying to replicate what I had seen in the videos. The feeling of a penis in my mouth, with my best friends fingers inside of my vagina was pushing me over the edge. It was only another minute or so of sliding my lips down Michaels shaft until I started having my first real orgasm. I thought I had had them before that, but as they say, You’ll know.

I let his penis slip out of my mouth as I leaned over, falling flat on the bed enjoying my orgasm. “You think that’s good, wait until you have it inside your pussy.” Megan said. “Help me take your pants off.” She said as she struggled with them. Michael gave her a hand, and soon they were laying on the floor near the closet too. Then Megan slid my panties off as well, and I was laying there naked.

Megan slid up the bed and moved over to where she was laying next to me, but with her head looking down at my vagina. Michael got off the bed, and looked down at us laying there. He stood there watching with his pole in his hand, stroking.

Megan started running her hands over my body, kissing each spot she touched. She kissed my stomach, then down to my clit, then teased it with her tongue. I nearly sat up in shock. It was one thing to touch your own clit. It was another to have someone elses tongue on it. She started kissing and flicking my clit with her tongue, while playing with my breast in her hand, and the while Michael stroking while looking on in interest.

Megan licked my vagina for what felt like hours. It was the best thing I’d ever felt. That day was full of those moments. After a bit though, Michael was getting a little antsy. “Honey, I know you’re enjoying yourself there, but can I cut in?” He knelt on the bed between my legs, waiting for her to move her head. He looked up to me, and with a gentle look on his face, said: “Can I make love to you?” I nodded slowly, while Megan moved her head out of the way.

Michael slowly pressed his shaft into me, slowly filling me to the hilt. My eyes rolled into the back of my head. He was gentle, and at any sign of pain, he stopped pressing. He kept asking if I was ok. After my third minor wince, Megan leaned down and started licking at the sides of his penis and my vagina. That made me thrust upwards on his shaft my hips trembling.

Megan then pulled back and started kissing and nibbling on my nipples, while watching Michael pick up the pace a little and begin thrusting in and out of me. I was in heaven. My father was wrong. THIS is how you got to heaven.

Anyways, I feel like I am rambling or putting too much detail into this story. So I apologize if this is much too long. I may have a detail or two wrong, but this is the story of my first time. It was probably the best day of my life, and I’ve yet to do anything like it again.

[my-very-first-time]

First Time Sucking a Cock and Forced To Be a Sex Toy for an Older Man!

submitted anonymously

When I was 14 (I was pure pussy!) and a freshman at high school. My track coach and English teacher, an older man in his 50s, use to drive us to track meets. Afterwards, we would hang out at his house eating pizza and watching video games.

One day, after school, my track coach, Mr. Davidson, offered to drive me home. At first, I said, “No.” Because I didn’t want him to know where I live. But, it was getting late and I did not want my mother calling around looking for me.

Mr. Davidson put his hand between my legs and my little cock got so hard. Then, he unzipped my pants and started to stroke my hard cock. I was about to cum when he turned the corner and I told him to let me out about half way to my house. Once in my room, I exploded my load all over my stomach.

For the next year, I would lie on his bed and I would let him jack off me two or three times. Mr. Davidson would get behind me in the shower and stoke my hard cock until I was sore. Each time, he would jack me off, I would be totally naked, and he would be fully clothed. I got use to taking off all my clothes when I got to his house.

By my sophomore year, I was sucking his cock and wearing panties. At first, I hated wearing frilly girly panties, but Mr. Davidson said I need to be focused on sucking his cock. One day I was so into stoking my cock that I completely got distracted about sucking Mr. Davidson. He flipped me over his knee and spanked my ass till it got so red. I couldn’t sit for a week.

My junior year, in high school, I was sucking Mr. Davidson cock on a regular basis. He had my eat my own cum and then he would cum on my ass. Now, I would come over his house and lay on the bed naked. Mr. Davidson loved to watch me cum with a dildo in my ass. He would grab my cock and tell me that my cock belong to him!

During my senior year, I was the best lil cocksucker and panties slut. Mr. Davidson had me forced to dress like a girl. Later, in the evening, he would tied me up on the bed or chair…exposing both my holes and fuck me silly. He would make suck him and then take his load up my pussy ass. I became a Daddy’s girl…a sex toy, a cocksucking bitch whore who loved to cum!

[my-very-first-time]

Brotherly Love

submitted anonymously

When I was growing up, I shared a room with my brother.  My brother was 2 years older than me and we really didn’t do much together.  We didn’t have much in common and hung around with different friends.  I used to take the opportunity to catch a glimpse of him in his tighty whities and he filled them out nicely.  

I was around 15 or 16 and we not only shared the room, but we also shared a double bed.  Every now and then, my hand would accidently brush his ass or something when I was rolling over but I didn’t expect anything to happen. 

One night, he said his muscles hurt and would I give him a back rub.  I protested and said I didn’t want to touch him but secretly, I did.  He started to pick on me and said that I better give him the back rub or he was going to beat me up.  Finally, I gave in.  I started to rub his shoulders, nice and broad, and I was enjoying it.  He said to rub lower so I worked down to the middle of his back.  After a few minutes, he said lower so I moved down to his waist.  My fingers kept getting stuck on the waist band of his briefs so he moved them down to the middle of his ass.  I rubbed for a bit longer and told him that my hands were getting tired.  So I stopped and rolled over to go to sleep.

A couple of nights later, he wanted it again so I went through the same process. This happened a few times and one night after I got tired, I went to sleep.  I woke up a while later and his cock was touching the back of my hand.  It was still in his briefs but it was definitely hard.  I left it there and every now and then, he would push it against my hand a little harder.  I enjoyed it and I think, but I’m not sure, it seemed wet.  After a while, my brother got up and headed to the bathroom. When he came back, he kept his back to me, so I went to sleep.

This seemed to become a regular thing and one night I decided to take it a little further. When I was done giving his massage, I rolled onto my back and let my hand rest against his ass.  I waited a while and then started to breath heavy pretending I was asleep.  My brother then rolled over and his cock rested on my hand but this time, he had pulled it out of his briefs first so I was holding onto his bare cock.  It was really heavy.  He is hung much larger than me.  It was at least 6" or more and really thick.  His balls were the size of limes and heavy in his ball sack.  I lay there still pretending to be asleep and he started to move his cock so I was kind of jerking him off.  He did this very slowly and I’m sure he was trying not to wake me up.  I was really enjoying it so I began looking forward to this almost every night.

Finally, one night I couldn’t resist and when he put it in my hand, I closed my fingers around it.  It startled him for a second and then he started fucking my hand.  No words were spoken.  He really began to get into it and I felt him tense up and his cum shot across my stomach.  He lay there for a few minutes, completely still and then rolled over to go to sleep.  I got up and went into the bathroom.  I stood in front of the mirror looking at his cum running down my stomach.  I ran my fingers through it and and then started to stroke my cock.  I didn’t realize that I was using it as lube but it felt so good. I had the biggest orgasm I had ever had.  Just before I started to wash it off my hand, I decided to take a little taste.  I licked just a little bit and at first thought “yuck” but for some reason, I decided to try just once more.  It wasn’t as bad but I washed it off and went back to bed.

This became a regular thing from then on.  Although we never spoke, I got to stroke him off every night.  One night, I was very adventuresome and decided to move down in the bed and when he rolled over, his cock rested on my cheek. I don’t think he was expecting it but he moved it back and forth across my cheek.  Finally, I rolled my head and it was rubbing against my lips.  My tongue was sticking out a bit and I was tasting the underside of his cock.  At one point, I opened my mouth and his cock head entered.  I could taste his pre cum and it tasted wonderful.  I decided at that point, I was going to go for it and took it into my mouth.  He must have liked it because he started to fuck my mouth.  I took it deeper and deeper until I had his balls resting on my chin.  He held it there and just pumped his entire load down my throat.  I was surprised that I didn’t really taste it.  Now I know that I should have pulled it out of my throat and let it cum in my mouth.  

We did this for a couple of years until he moved out but to this day, we have not mentioned it.  I would love to do it again but I don’t think that will happen.

[my-very-first-time]

Sunday Pants

Submitted anonymously

(This will sound like complete wishful thinking, but it actually happened.)

When I was 12 my mom sent me to buy some new ‘Sunday pants’. I was growing quickly at the time and horny as hell. The salesman was familiar to me as a member of our church choir so when he said we needed to go in a dressing room to get my measurements I trusted him. I’m sure I set off his gaydar and I found him an attractive mid-30s guy. Once inside the dressing room he told me to take off the shorts I was wearing so he could get accurate measurements. I quickly complied as I really wanted him to see me in my briefs. Of course I was completely hard at this point, but he went about his business of measuring my waist with no inappropriate contact and only lightly grazed my covered balls with the back of his hand as he squatted to get my inseam. Then, when he stood I could see the outline of his hard cock in his work slacks. I suppose he could sense my interest and lack of hesitation in standing there as hard as he was.

Then, with no words exchanged, he grabbed the waistband of my briefs and quickly tucked it under my balls. He began stroking me with the loosest grip possible, just barely grazing my shaft and engorged head, while he pulled a handkerchief out of his pocket. Within 15 seconds I shot a geyser of young spunk into the handkerchief. After he wiped me clean, he told me he would be right back with a few pairs of pants for me to try on.

Upon his return he handed them to me through the door, but didn’t reenter. I chose my favorite pair, paid, left and never had a significant interaction with him again. I’ve never written this down before but have always been thankful for the experience.

[my-very-first-time]

'Gay-cub'

I’d been through primary school interested in the lads and the girls that I got close enough too but never thought of kissing, let alone anything else, because at that time all things like that are yucky! 

There was a boy in the year above me when I was in year 5, who would constantly be flamboyant and very camp all the time and I had no idea why.

One day however we seemed to walk the same way home and I questioned him about the way he was, he said because his big brother was always like that and he looked up to him, he said he wasn’t homosexual, it was just all as a big joke.

I really didn’t understand the idea of how it was a joke buy continued to do some searching on the Internet, when it hit 6'clock because that was always the quickest time the Dail-up would connect!

I had a little look while my family were in sparate rooms to see what being gay was actually all about.

When I saw these images of the very attractive men all muscular and with these thick bulging cocks, I couldn’t help but notice I had all of a sudden become hard. I ignored it, quickly shut everything down and found it hard to sleep that night because of it. 

A couple of days had past which meant it was swim class Tuesdays! My one favourite day of the week because all of my male classmates would go into the communal changing area, strip down, and put on the tight speedo trunks to do a couple of laps in the pool. All because we were all being trained to swim just incase there was ever a flood.

There was always one lad who I loved to stand next to when we got changed, his name was Jake, he always seemed to have a great tan and his deep blue eyes always made me loose track of anything I was doing.

He had a lovely dick, obviously small at the time but seemed to be much bigger than mine and anyone else’s in there, and he knew it.

He’d run around hitting people with it and swinging it around ‘for a laugh’.

It was always so hard to pretend I was disgusted when he hit it on me, I remember I’d always run into the toilet so I could place my dick in my wasteband so it wasn’t so obvious that I was erect.

Jake moved schools a couple of weeks after that,  because his mum moved house. It wasn’t until high-school when I saw him again and he hadn’t grown into his young looks at all. 

But by this point, there was a new boy I was interested in, there was Jacob, or ‘gay-cub’ which everyone called him because he had Brown hair with these blond highlights and, as kids, that was more than enough of a reason to pick on someone! 

Jacob was a very good swimmer, he’d be off school so much doing swimming Gala’s all across the county.

By year 8, I’d met his friend Ryan and we hit it off really well, we had all the same interests and became really good friends.

One nightnight, in year 8, Ryan had a sleepover in his house, which I was invited to, and when I turned up, I found out that Jacob was also there.

We had a good laugh and joke and by 11 O'clock, Ryan had fell asleep and me and Jacob were the last two awake and we decided to play a joke on Ryan.

It doesn’t seem that funny now, but we placed this foam rocket on his chest so everytime he took a breath, it looked like he was sucking off this rocket! 

Me and Jacob laughed about it and we got onto the conversation of masturbation.

I remember he said he was hard, and that sentence from him, pretty much instantly made me hard.

There we were, 4 foot away from one another, with a blanket to cover what each other looked like, both really hard.

He asked me if I’d ever seen another dick before, I’d told him about some of the porn I watched, to which he quickly corrected me to 'in real life’ .

I told him no,

to which he stood up,

dropped the blanket

and displayed a hard on, no bigger than my little finger pointing up to his chin.

I felt like I had nearly came in that moment.

I tried to act all disgusted but I couldn’t, I looked at it for so long until he said “you’ve seen mine, can I see yours?”,

I wasn’t listening to him as I was so fixated on his dick, he pulled the quilt off me, revealing my, much bigger dick. He was shocked, he said mine looked huge! 

What happened next was something out of one of my dreams!

He knelt down,

grabbed me with his small hands

and put it into his mouth,

I, very close to Cumming, pushed him off and back to his bed where I went down on him so hard.

His dick was no were near making me gag, but I was enjoying it so much. 

While I was helping him out, he all but lay a finger on my dick and I shot a load on poor Ryan’s floor.

I looked up at him, red faced, so embarrassed, and we just laughed.

He didn’t cum as he told me he never had before, we went to sleep in the end and never spoke much about it for a couple of weeks.

In the following year we visited each other, but it seemed to be me more interested in helping him out, and he didn’t really want to touch me.

In the end, he moved schools and we stopped talking.

I still have him on Facebook and do check up on him now and again, the worse thing is, he’s built like a house and wears all these tight clothes now.

To this day he could come up to me and whip his dick out, and no matter the size, I’d still suck him dry. 

[theadults]

Hey everyone! I will be doing an #AnswerTime here on Tumblr tomorrow at 11am(PT)/ 2pm(ET) to celebrate the relaunch of my tumblr page and just to have a good time with all you beautiful people! theadults.tumblr.com/ask.

[my-very-first-time]

Hey Sean, tell us about your first time. Yeah, that time.

[nebraskadude]

My First Gay Experience: Honestly, this is 99% true.

My First Gay Experience: Honestly, this is 99% true.

It was the summer between my freshmen and sophomore years of high school. Everything was going normal until one day out of the blue I got a text from Andy. You see Andy was a junior, a varsity wrestler, and popular. Not just popular, but he was in the top dude pack. They all walked around together, ate lunch together, and come to find out they did nearly everything together.

You can see why I was surprised when I got a text from him. Not because I wasn’t popular, but because he was on a whole different level, and I had only talked to him a handful of time.

The text said “Dudes only camping trip this weekend, I’m allowed to bring on guest. You wanna join?”

Of course I said yes, after asking my parents. Haha. Here I am packing to go camping with the most popular dude in school. I hadn’t been so excited in my life. At this time I had no sexual attraction to guy so I wasn’t even thinking about the possibilities of what could happen when the sun goes down. Finally the day came, Andy pulled his green Dodge ram into my driveway. I threw my gear in the bed of the truck and jumped in the passenger’s seat. It was a short hour and a half drive to the campground we were staying at. The drive was pretty uneventful, we just talked about school and girls, you know the usual guy shit.

Once we arrived we meet up with the rest of the group, there were about 15 of us. We all set up our tents, everyone had to share a tent with someone, so naturally Andy and I were tent buddies. The rest of the day we all just hiked around and went swimming in nearby pond. This was the first time I could say that I was even the slightest attracted to another guy. They were all stripping down, saying that the water felt better naked. How could I resist, after I didn’t want to the only one left out.

So many cocks, so many hot bodies.

I wish I would have snook a picture of us all… After we all cooked dinner and sat around the fire it was time got everyone to sleep. Andy and I just laid there in silence for a bit, and then we started talking about girls, then talking about jacking off, and how many bases we’ve gotten. Before I knew it I was hard as a rock and from what I could tell so was Andy. Luckily he had the balls to ask me if it would be cool if he jacked off. I said “yeah, as long as I can too”. We started off in our sleeping bags. I went into detail about a porno I saw where two girls were fingering themselves then they both help each other out. After a few minutes of jacking in our sleeping bags it was really hot in the tent. Andy unzipped his bag and just laid there for me to view, his cock wasn’t any bigger than mine, about 7 inches. But it was the first hard dick if seen in real life. I quickly followed, unzipped my bad and laid on top of it. Just laid there stroking my dick, eyes closed except the occasional peak over at Andy to check out what he was doing. While I had my eyes closed Andy asked me if guys help each other out sometimes. Before I could reply his hand was on my Dick. It was one of the best hand jobs I’d ever had. Of course I reached over and helped him out for a bit. “Have you ever had a BJ?” Andy asked. “Of course” I replied. We both went on talking about how good they feel and how bad we wanted one right now. I could feel the pressure between us, I was hoping they he would just lean over and suck my cock at the point. That’s not what happened, he said that he would blow me, but I had to blow him first. Reluctantly said I would give it a try, but no promises. I could feel the heat radiating off his body as my mouth got closes to the tip of his dick. I just went for it, started sucking. In the distance I could hear a train whistle blowing. His cock tasted much better than I thought it would. When I was stopped for a moment I could see the pre-cum oozing out of his cock. I loved the vein running down his shaft, it was an amazing cock. After he said that I had done enough and it was his turn to try I laid back down. I was tired from all we did that day, seriously about to fall asleep. He went down on me, and I fell into a light sleep. All I remember his waking up briefly, I told him I was about to cum. He said go for it. I shot it deep into the back of his throat…then passed out.

When I woke up the next morning Andy and I were laying naked next to each other. I got nervous about what we had done that night; I didn’t want the other guys to find out. Just then Andy woke up first words out of his mouth were “I won’t tell anyone if you won’t”

More stories to come in the future, hope you enjoyed.

Please like or re-blog this if you want more stories, or don’t and I wont post anymore. :) 

[my-very-first-time]

[my-very-first-time]

First day in high school - the gym showers

[paulsposts]

[lukepackwood-deactivated2019011]

packwood

[littlelily95-deactivated2015050]

PrettyKitty95

[my-very-first-time]

-Miles-

[my-very-first-time]

Like I was a Woman

I met him on the internet, that's how all great relationships start, right?

He was a sophomore at the state university, the cliche example of tall, dark and handsome. Towering over me at 6'4, my head barely reached his chest.

He cooked me dinner, he took me to a play and brought me back to his apartment.

I lied.

I lied a couple times actually, I wasn't 16, I was 15 and I most definitely was a virgin.

Maybe I was scared to seem immature? Either way, I walked into this like I knew how I wanted it and what I was doing, in reality, no man had ever touched me.

I got high.

I got really high actually, being a 5'2 15 year old girl weighing 110lbs on a good day.

Maybe I was scared to actually letting him take me?

Time seems to dissolve.

He took my clothes off, he took my clothes off like I was a woman, like we'd done this a thousand times and this was just the last page until he got to his favorite part of his favorite book.

He laid me down. Everything seemed to be happening in a frame by frame, one picture after another.

His lips touched mine, down my neck, my shoulders, my chest. My stomach sank in.

He pressed in.

When they tell you that it hurts, you get scared. When you hear the stories of all the other girls and how much it hurts you almost second guess losing your virginity at all..

But, when you feel it for the first time and you feel how much it hurts.. and all you want is for it to hurt a little bit more.. You rethink some things.

After he was finished, we cleaned up and I laid on his chest. I did it. No longer a virgin, No longer a girl and destined for some pretty kinky future sex.

Boom.

[bigbangsheldon]

[shamyforeverlove]

Her hair 😂😂😂

[my-very-first-time]

Well now, here we have a twofer. Neither Sheldon or Amy have had sex before so this was extra special for Their Very First Time.

[my-very-first-time]

Boss's Son

From the Closet

======================================================= When I was 15 I worked on a construction site. My Dad had an electrical contracting business and he had me help out on one of his big projects. They were installing Air Conditioning in the local Hospital, yes AC that is how long ago it was and though I was too young to work my father paid me $50.00 a week to be a go fetch boy. 

They had built a huge metal building behind the hospital and that is where they fabricated the air handling ducts. We also keep a bunch of electrical supplies back in there also. About 6 times a day I would head out there to get connectors, or junction boxes or some other items to take to electricians working in different parts of the building. I also discovered that is was a great place to disappear for a short nap. The conduits were stacked across the back of the warehouse and you could crawl in to find a dark, cool spot for a nap after lunch.  One day I was back there and I heard voices and looked out the end against the warehouse wall were two guys talking. I crawled closer so I could hear what they were talking about. One was trying to talk the other one into doing something and although not arguing it did seem to be a excited conversation.  Then one of the guys dropped to his knees and pulled open the others pants. OH my gosh, I was so excited I was sure they could hear me breathing. The guys on his knees pulled out the other ones cock and begin to kiss it. I was pretty naive at that age and while I had been in a couple of circle jerks with neighborhood kids no one had ever suggested sucking each other's cock. Then he opened his mouth and took the other guys cock all the way down his throat, you could tell by his cheeks he was sucking on this fellow's dong and from the sounds they were both making they were enjoying it. All of a sudden the guy sucking backed off and cum went everywhere. It came flowing out of his mouth and around the other guys cock and dripping all over the floor. I was so hard I thought I could just cum in my pants this was so hot. I had never imagined that two guys could do this to each other and I couldn't wait to try. I watched as they cleaned up and could not believe my eyes. Later I saw the guy who had received the treatment, I recognized him from his green work pants and the boots he had on. He was about 6'2" and had a working guys frame, somewhat thin and very attractive. I am not sure I had ever thought of a guy being attractive, but I also realized that it was what was between his legs that caught my attention.  Two days later I was back in the conduit when I saw the guys legs. He shuffled around for a while and it looked like his friend wasn't coming. I was scared but I was also motivated so I crawled down to the opening. He was standing there rubbing himself and I looked out and said, "Is that something I can help you with?" He was shocked but after a second he said, "Your dad catches you doing this and he will fire me and tan your hid!" I smiled as I crawled up to him on my knees and said, "He has to catch us first."  Jack, that was his name, pulled down his zipper and pulled out his cock and balls. I couldn't believe I was going to get to do this and I promised myself that I wouldn't waste a drop of his cum. First I licked the head of his dick and slowly begin to work my way down the veined shaft. God he tasted so good and it was such an unexpected pleasure. It had never occurred to me that another guy's dick would taste good, it was musky and slightly salty and the smell was unique but oh so exciting. 

His dick had grown to about 8" and I wasn't sure I could get it in my mouth. I let my jaw go slack and begin to suck on him. He patted me on my head and said, Careful with your teeth. "He reached out and held my head and slowly began to fuck my mouth. He was careful not to gag me and to this day I realized that his special and careful treatment for my first time caused me to enjoy the act of cock sucking. He didn't last long and after a couple of minutes he shot into my mouth. It tasted salty and tart and I was surprised at the flavor, but I swallowed as fast as I could. Not so much because I like the taste but to keep from chocking. He was catching his breath and I was fascinated with his nuts and just wanted to lick and suck on them, but he put everything back in and zipped up. He helped me up and reached down to feel me through my jeans when he noticed I had cum and had a wet spot over my crotch. He laughed and said seems like you enjoyed it also.

Jack and I met a couple of more times before my dad moved me to another work site. I don't think he ever knew, just had something else he wanted me to learn. I must had been 5 years later that I came across Jack on another summer job, that summer he taught me some other things guys could do together in his trailer. It was a very good first experience. 

[my-very-first-time]

[my-very-first-time]

Belgian Slave Gets His First Figging

To be honest I had never heard of this particular activity. Then I read this story on FetLife and I was fascinated. MASTER has graciously allowed his Belgian slaveboi to be featured here today. My humblest gratitude to both.

================================================================

After returning from my summer holidays, my online MASTER started discussing the possibilities of figging. i had been interested in this for quite some time and therefor bought a piece of ginger in my general department store prior to our session of Friday, August 21st 2015. Although it was my first time ever, i knew i had to take a solid big enough piece of ginger to use

Prior to the figging, my MASTER had my douche out my rectum. This preparation for the figging went smooth and easy but felt exciting because it was about trying out something new.

MASTER made me peel the big bulbous end of the ginger root, using a patatoo peeler. Than HE made me lay back in my homemade travel sling wiith my boi-cunt exposed.

The figging itself was a new, strange but also exciting and satisfying experience. Inserting the piece of ginger without using lube wasn't easy. MASTER didn't want me to use any lube or water to prevent any dilution of the ginger juice. i might have picked a piece that was to big (my eyes were bigger than my ass ;-) but in the end i was happy to get it in.

The burning sensation cause by the ginger was much stronger that i had been hoping for or was expecting. MASTER made me repeatedly constrict and relax my boi cunt muscles to increase the sensation and burning effects of the figging. He made me endure the effects even when i pleaded for the ginger to be removed. This made me twitch even more. The uncomfortable feelings were strong but not beyond bearing. my MASTER had me working my nipples and wanking my cock as a distraction, and this worked well.

MASTER wanted to edged me. When i got close to cumming i was very surprised i wasn't able to hold on to the cum any more. i experienced a ruined orgasm even though i have had almost two years of training in orgasm edging. i guess that the sensation caused by the ginger got my cock to explode.The fact that i was able to reach a second climax when MASTER allowed my to jack some more after unclamping and reclamping my nipples indicates that the first climax was ruined.

I was glad when MASTER allowed me to take the ginger out. i was expecting and hoping that the warm feeling would remain for the rest of the day but it was over after half an hour.

Like always when MASTER fucks or plugs my boi cunt, also on this occasion my cock went limp.

Thank YOU, MASTER, for initiating me to this new experience.

I am looking forward to be figged again.

[my-very-first-time]

Birthday Boy (part 2)

Our favorite Scotsman continues to share of his first time experiences. Part one dealt with his first with a female (2 actually). But there was another first a few years later. His first with a guy. And it happened a long way from home.

==========================================================

I'd been with my unit a few months and was getting on well with the lads. They gave me the nickname "hazard" due to the fact that I was safe until used incorrectly. There was one guy I got on really well with, the " ginger princess," called that because it was known he swung both ways and couldn't handle his beer. We got on well together both being from the highlands of Scotland, our love of curvy tattooed women and we both liked a good sparring match.

Fast forward to the wonderful landscape of Afghanistan, where everything is trying to kill you. The gp and I had been assigned to work In a forward outpost. Gp was the platoon medic so we all had to rely on him to save our sorry asses if we got shot or blown up. My job was the platoon signaller and for some reason the heavy gunner.  It was fair to say he got the easy jobs. It was always like that maybe because he knew who to suck up to. while I knew how to piss people off.

Outpost life was dull behind the walls. We spend most of the day working out or sleeping in the sun.  The ginger princess and I still acted the same as ever, having our wee fights, giving each other rub downs after patrol or working out and and spooning one another through our sleeping bags. ( I was the big spoon most days).  It was all fun and games and the other guys bantered how we had a bromance but it was all in good fun.

One day before our routine patrols, gp and I were having a game of poker and  I was losing ina major way until one hand when he got 'cocky' and bet me a blowjob. He had beaten me and thus had all my wages that month. Let's just say the look on his face when he saw my cards was more than enough for a victory to me. I walked away laughing and teasing him to make sure he had some mouthwash on hand as I was going to do my best to make him regret the wager.

My section went out on patrol that day and it was all fine until we got to the local village. Something was off.  Normally the local kids were harassing me for my sweets but today, nothing.  I reported my suspicion to the corporal but it was too late. A round hit the side of my helmet sending me to the floor. Next thing I know there was an eruption of gunfire behind me and In front.  I quickly got to my feet feeling a slow stream of blood thickly oozing down the side of my face. Thank God for my stupid thick skull or I would've been concerned it was serious.

I started to lay down suppressing fire to allow my section to get to good cover.  When we got to safety we did a quick body check. Someone was missing. That's when I saw the kid 100 metres away stuck in s ditch. He was wounded and I could see him treating his leg with a bandage. I dropped my bag, grabbed my ammo and linked it together. I told the boys to get cover fire sorted and radio back up for a sitrep. Before they could ask why, I broke cover, firing my gpmg from the hip at the enemy's position. I began a slow advance to the kid's position, round casings falling rapidly at my feet. I could hear my section behind me doing the same as me, giving it their all to give me cover. I stopped firing and rushed to the kid's side.

When I got to him he was trying to apply his pressure bandage properly. He was scared, hell I was scared but I couldn't let him know it. "Hey, you trying to outdo me, you little cunt.?"  "Aw yeah, got to beat your reputation."  I couldn't help but smile, sorted his bandage out and told the section the situation. They were glad to hear he was okay and his humor was still attached. I told them to throw some smoke and give me some cover as I was going to be dragging him back to the rest of the section.

As soon as I heard the roar of my cover fire I started to drag the kid along the dirt. I'd gotten us half way there when I felt a pain in my chest.

I'd been hit.

I hit the ground but had enough strength to throw the kid into another ditch a metre away but I was stuck. I turned to the enemy's position and saw them advancing on us. I pulled my pistol out and fired. I wasn't letting them get near us.  

Then it was darkness.

I woke up in a clean room and a soft bed.  My first thought was that this was hell.  Then I saw the ginger princess sleeping in a chair. He was out cold. It wasn't til a young nurse came in that I found out what happened. I'd been hit again which knocked me out and when they checked me over they realized that I had bleeding on the brain from my first injury so they put me in a coma.

I'd been out for 3 weeks.

GP had arrived two days earlier on leave and had not left my side. I sat myself up and with one mighty swing I punched him in the face. He fell out of his chair started shouting until he realized that it was me. I thought he was going to hit me back but he kissed me instead!  It was the first time I'd kissed a guy; it was strange. It was a lot stronger than kissing a woman but felt just as nice. He broke away in tears, telling me I was an idiot for being so reckless.  He told me that I'd died and he brought me back.

I gave him a slap to stop him from talking. "What the fuck is that for?"  "You forgot the bet, princess.  You owe me a blowjob. No way in hell was I going to die before you paid up!"   We both started laughing but then I went in for a second kiss.  This was more relaxed, he was letting me lead. It wasn't long until I could feel his hand moving over my stomach slowly reaching down to my hard cock. He gripped it hard in his hand and started  to slowly pull it up and down. It felt amazing but it wasn't long til I was cumming (It been nearly 4 weeks since I'd done it myself).

He broke the kiss to lick the cum off his hand and my cock. "Don't go soft on me Hazard. I want you to fuck me yet.  He then took my cock in his mouth, rapidly bobbing up and down trying to keep me hard. I reached over to his crouch and grabbed the outline of his cock though his tight jeans. Without asking he unbuckled his belt and top button so I could get access.

His cock was a little smaller than mine with a slight curve. As I began to slowly rub it he started to moan on my cock. The more he moaned on my cock the better it felt. I then put my hand around his back and went down to his firm ass.

I began to slowly creep my finger into his tight asshole. It took a while with no lube to get it in but when I had he couldn't hold back the moans any more. He dropped his jeans and straddled me on the bed. He started to kiss me again and grinded his ass against my cock. "You ready?"  "Ready for what?"  

It was then I could feel my cock starting to slowly push inside him.

His moan became a lot deeper and slower as he grinded slowly on my lap. The feeling was nothing I'd ever experienced and yes was better than any girl I'd done with before and not been able to compare with since. I began to rub his cock again til he came in my hand. Exhausted by this he started to slow down, but I wasn't going to let him. I started thrusting hard into his ass. But it didn't last for long as the idiot bit down on my stitches and I then gave him a right hook!

Had to lie to the nurse that I'd sneezed and they burst. Fair to say she didn't believe a word and left us each her number. I chucked it but the ginger princess kept it. Two years later I was the best man at their wedding. It wasn't til that night I found out how well she had taken care of the troops.

[my-very-first-time]

into the woods

submitted by anonymous

=========================================================

My first sexual experience with a guy was very short and one-sided. I was almost sixteen and still remember it very vividly. 

His name was Jack. He wasn't the cutest, but what can I say? I was a horny, budding bisexual boy. He was a year older than me and claimed to be "straight." We weren't even hanging out. 

His older sister was friends with my older sister and she stopped over at my house, and Jack tagged along. While his sister went inside, I decided to go outside and talk to him. He was standing by the side of my house, in the woods. I slowly walked up behind him and talked to him. 

We were talking for a while, and being that I am a feminine person, he asked if I was gay. I quickly said no and told him that I was bisexual though. At that moment, he took me further into the woods, pushed me onto my knees and pulled out his dick.

It wasn't very big, only like 5 inches. He pushed my head closer to it, and I began sucking. I remember admiring the feeling of it in my mouth. I'm sure I was bad at it at first, but it couldn't have been that bad, because he began moaning. This went on for about 4 minutes, until he started cumming. 

I remember the taste, as his cum was salty and disgusting. I quickly tried to pull away and let him finish the rest out of my mouth, but then i realized that he was holding my head there. I felt obligated to swallow. 

When he was finished, he pulled up his pants, zipped them and then thanked me. I just left.

We haven't talked to this day, 4 years later. I think about it now and can't decide if I'm mad that he practically made me suck it, or if I'm kind of glad..

......