I [M18] got drained by my two female friends at a sleepover (Part 1).

This story happened when I was 18 (almost ten years ago), last year of high school, and remains one of the only cool things that happened to me in those years. I’ve often hesitated to tell this story but I couldn’t manage to sit down and do it, and didn’t know where I would even post it. But having been a long time lurker, I thought: “why not?” (I didn’t expect the post to be this long so I’ll divide it in two parts)

Throughout high school, I never was a cool kid. I wasn’t awkward or shy or unattractive, but I just kept to myself and always felt too crowded. In my last years, I was in the drama club as a stage hand and simply helped around for the plays and drama games.

In this class, two girls that had been best friends since their sophomore years began taking a liking to me. They were kind and playful, waving at me in the corridors and really, sincerely, caring for me. I always felt like they were the big sisters I never had. We started talking, texting and going out. I often wondered if they thought I was gay because, let’s be honest, even today, people are weird about male/female friendships. But we became such friends that they also teased me about girls, sex etc, confirming that they didn’t doubt my sexual orientation.

We had been friends for a good half-a-year when they asked me if I wanted to come to a sleepover. Now, I feel, is the time to give them names and describe them to you a bit. There was Annie and there was Carla (fake names obviously). Annie was taller (slightly taller than me at that time), broader (in a sexy, Ashley Graham way), and full of life. Carla was short, long dark-haired and with big tits (so big for her frame that she had been teased about it for a long time), she kinda looked like Ariel Winter in terms of proportions. I asked them what the plan was and it was Carla who invited me to her home to just chill and watch tv. Though it felt stupid, I remember asking them if it wasn’t weird because I was dude, and they just burst out laughing saying they wouldn’t have asked me if it was weird. So, I accepted.

Carla lived in a modest home surrounded by high bushes in a narrow country road. When I arrived, Annie was already there so they both welcomed me and we slacked on her sofa, ate chips and laughed watching some ridiculous reality show. Carla’s parents weren’t there so we could enjoy the house to the fullest. Now, after we had ordered pizzas and ate it, Carla and Annie left to take their showers and slip into their pyjamas, then they invited me to do the same. I had brought some simple pyjama pants and a t-shirt. After showering, I remember feeling awkward because I didn’t know if I should go to Carla’s bedroom or wait for them in the living room. So, I eventually opted for the second one. But, Carla texted me from upstairs asking me what took me so long, saying they moved to the bedroom to watch the show and pump my inflatable mattress.

I jumped up and climbed back upstairs feeling silly. As I approached the room, I knocked and they both teased me though I defended myself saying I didn’t want to walk up on them without warning. They were both in different attires and I really tried my hardest not to feel turned on. Remember, by that time, I had never had a girlfriend, never saw a woman naked, never had sex. And suddenly, I was in Carla’s bedroom, her dressed in loose sleeping shorts and an oversize pink t-shirt revealing the outline of her nipples, along with Annie dressed in a thin pyjama set that made her ass look huge and leaving a constant little gap in her top due to her tits pressing against the buttons. At first, we all sat around laughing at the tv until hours passed and both Annie and Carla slipped under the covers. They seemed to feel bad for me so they cackled as they invited me to lay in bed too. Carla had a king-size bed but I knew that if I joined them, we’d be all crammed like sardines. Yet, I really felt stupid sitting on the ground so I didn’t refuse their offer.

I bounded on the bed eagerly, making them giggle and buried myself between them under the covers, rubbing myself against their two warm bodies in the process. They started teasing me because their legs were freezing cold so they kept touching me to make me jerk up. Carla’s boobs were so big that they spilled on both sides of her and brushed against my arm while Annie’s waist was so wide it pushed against me the whole time. The moment it turned sexual was when they stopped caring about the tv and began talking to each other about intimate stuff I didn’t feel welcomed to add anything to. Until… they started asking me questions.

Annie started by asking me what I thought about her. Carla was shyer, or more modest I guess, but Annie had always been very frank. I told her that she was fine but she ordered me to be more detailed. She said that even if we were friends, I was still a guy so I would obviously have an opinion. I guessed a long time ago that she was insecure because she was a girl that was taller, thicker and she also had braces. But, I was going to be honest with her. I remember telling her: “If you want to know if you’re hot, then I’d say yes. But I’m just one dude.” She smiled and pushed me playfully before hugging my face, her boobs pushing against my chest and chin. Carla laughed along and asked me the same question so I replied that she was sexy too but admitted that neither of them were especially my type because I always had a leaning toward cute blondes. They pretended to be offended and pushed me off the bed teasingly before saying I should apologize. I apologized snarkily but they said they were owed something and Annie just randomly spewed out that I should kissed their feet. I grimaced at them and Carla said: “Don’t be cruel! Let’s say a kiss on the cheek for each of us”. So, I crawled on the bed toward them and pecked them both on their cheeks and they cheered before welcoming me back.

But the conversation didn’t stop and Annie asked what I found the sexiest about them both. I blushed and stuttered before saying that they were “well-shaped”. In retrospect, it sounded really stupid, but they were both flattered and asked me to elaborate. I struggled my way into saying that they both had attractive assets (Annie had a wide waist/ass and Annie had large breasts).

They both died laughing and while Annie’s body turned toward me, Carla sat with her legs crossed. Annie said she suspected that I fantasized about them and I tried to defend myself even though I know she was being sarcastic. Then, Carla said that there had never been any way for them to reciprocate because you couldn’t really “check out” a guy’s dick unless he was in his underwear or… in pyjamas. I joked with them that it was truly why they invited me and they were as embarrassed as I had been. Then, Annie said that they should be able to take a peek since they had let me see them in their sleeping attires. I willingly played along and stood on the bed, turning around to their playful cheers. “I can actually see it hanging in there,” Annie had said wide-eyed before Carla laughed along. I instinctively put my hands before my dick and they said I shouldn’t cuz it was hot.

By that point, everything was still all fun and games, friends teasing each other and all, but when I sat back down, Carla asked me if I had ever seen boobs. I blushed even more and admitted I hadn’t and that I was still a virgin. They didn’t act too surprised lol and both embraced me, howling like they were petting a cute dog. I felt kind of stupid there but it quickly washed away because both were pressing they bodies against mine. I was happy about not having had a boner yet despite the circumstances, but I guessed it was because of the pressure. I could then see them both peek at each other behind my back and Annie burst out: “We could help each other, no?” then Carla, smiling shockingly, added, “Yeah… But it goes both ways.” They had both laid down again, both their bodies turned toward me. Carla’s t-shirt was trapped between her tits and Annie’s buttons looked about to burst. She didn’t have massive boobs like Carla but her position messed her shirt around a lot.

There was a silence and Carla took the lead saying, “Would you dare touch my boobs? I dare you.” I was so shocked I have to admit my hands trembled a bit. “You wouldn’t dare,” she kept saying as she pushed the covers down and pushing her rack toward me. I was so mesmerized it felt like I wasn’t thinking anymore. I just shyly moved my hands toward her as she reddened and chuckled. My hand laid on her boob and then I got a boner. She frowned at me and said to “go in” as in “don’t just lay your hand there and do nothing, idiot” so I just started squeezing it and it felt like the biggest water balloon. My hand didn’t even hold her whole tit. She then took my hand and pushed it away softly as she laughed. Annie cheered and applauded. “They are really nice” I said when they asked me how it felt. Then, Annie said that she felt left out and Carla removed the covers abruptly to reveal Annie’s shirt having rolled up to her breasts and she said “Touch Annie’s ass now!” Annie had a fit of laughter and then they both gasped and started pointing at my crotch repeating that I had a boner.

I knew they were playing around, but for some reason, it made me feel humiliated. Until Annie asked if they could take a look. Carla argued that she had let me touch her so only she deserved to take a peek. So, Annie said I could also touch her. She asked if I wanted to touch her ass and rolled on her belly. Her ass was enormous, both cheeks jiggling as she turned and her pants stuck in between before she pulled it out. I was more straightforward this time around because I wanted to show them I wasn’t timid. So, I put my hand on her ass cheek and began caressing and fondling it. She trembled and said she had chills so they laughed again.

Then, she turned back on her side and said, “Our turn now!” to which Carla added, “Show us the penis!” and they laughed again. “Do you want to see all of it? Should I stand? Or just take a peek?” they looked at each other and said, “Just pull your pants down.” So, I grabbed my pyjama pant and casually pushed it under my balls. They both gasped as their eyes locked on my erect dick. I don’t know why but they instinctively approached their heads as if to see better. “I didn’t know you were packing all that.” Carla had said and I asked if it really was big or if she was exaggerating. Annie replied that it wasn’t that big but it was beautiful. Carla argued it was average-sized but because she was short, it was big. We all laughed and they just kept staring so I pulled my pants back up slowly. “We are truly friends now!” Annie joked to end it all on a funny note.