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.
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.
