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Prom Night Threesome

Cindy had been naughty while I had been away at school. She always liked men a lot, and absolutely being pursed and fucking. And she was also very submissive and wanted to "please her man," such that I would tell her what I wanted to try, and she would just go along with it. What ended up happening that May was some less refined version of 50 Shades, because at the time that this took place, we were all children, emotionally at least.

I escalated our sexual activities as a part of this. Cindy let me photograph her naked (my parents had a Polaroid) or wearing nothing but lingerie and heels. No form of dirty talk was too much. Our fantasies expanded. She didn't want to masturbate initally, and wasn't keen on anal, but after I started denying her vaginal intercourse, she changed her perspectives on both topics. The colder and less affectionate I got, the more she tried to please me in every way possible. Was this healthy for anybody? No. Was the sex over the top and gratifying? For a 19 year old man-child? You betcha!

I met Jim 3 years before. We worked together in this pit of despair. Jim wasn't a bad guy. He was actually pretty friendly and a hard worker. But he had no filter. Soon he was telling me about his sexploits with this chick named Cindy. They were skipping school and fucking all day, and she'd let him do whatever he wanted. Each tale became more sordid than the last, and frankly I thought that it was all bullshit. We were really young at the time, and most dudes I knew who bragged about their sexual conquests were actually sitting in their bedroom at the parents' house -- finishing their pre-calculus homework before playing Nintendo and going to bed at 9pm.

I'd kind of forgotten about Jim when Cindy and I started dating. The sex started early and we did it often, basically any time I wanted it, although I rarely saw her naked at first. Both our families were conservative and Christian, so Cindy and I ended up having a lot of car dates -- where you'd be mostly dressed, in case you got caught and had to drive off in a hurry. It wasn't until we bumped into Jim at a local shopping mall that I put two and two together.

Cindy and Jim were clearly still into each other, no matter how much Cindy denied it. In Cindy's telling, when they were dating, they finally got caught redhanded. Jim's parents kind of shrugged about it, but Cindy's parents were having none of it. They forbade her from seeing Jim again, and sent her to some kind of "Christian sexual deprogramming" therapist. Suffice it to say that the therapy did not take. Jim would still call her frequently. He knew exactly when her parents would be out of the house, and nailed his landing every time. She claimed that she didn't want him anymore, but I knew differently. It was clear for all to see that they were still carrying a torch for each other.

I started reading a lot of erotic fiction on campus during my freshman year of college. I was away from home for the first lengthy time of my life, and I needed to have a sexual release in the absence of Cindy. I used the college's "internet systems" to read all kinds of smut about sex, swapping, etc by way of many user contributed stories. I had no idea that people did that stuff. At the same time, Cindy and I having a threesome kept coming into my dreams. And then my dreams started evolving into having a threesome with Cindy and Jim. Those dreams would happen time and time again. I never thought that I'd go through with it, much less be the one to initiate it, but...

At the same time, with my mother going back to work, I had the house to myself a lot during the day. That's when I escalated the activities with the nude photos and so on. It's just that we kept it to an hour, because that's about the amount of time we had between Cindy getting off work, and my mom returning home from her job.

Cindy was excited about her upcoming prom. She always liked getting dolled up, and apparently had been planning for this event for nearly two years: the dress, the heels, the makeup, the hairdo, etc. Better yet, her parents said that she could stay out all night, with a curfew of 6am. This was absolutely not normal on their part, but they relented because they figured that it would be the last hurrah for their daughter before they moved out of state at the end of the summer.

Little did they know that I'd gotten a hotel room and had every intention of spending the entire night being naked with their daughter and exploring various pleasures -- including a threesome, if all went as planned. Cindy told me that she'd also bought lingerie and heels for the occasion, but wouldn't let me see them. On top of it all, Cindy decided to use a contraceptive sponge, which wasn't really in her nature, but even she was aware of the amount of fucking that was going to take place that night. Little did she know that Jim was going to end up in the mix.

Cindy looked stunning in her silky black prom dress and stiletto heels. Her makeup and hair (strands of curls) were perfect. To my surprise, she was actually putting a little bit of cleavage on display. I'm surprised that her parents didn't forbid her from wearing that dress, to be honest. While she was 5'4" and thin, her 40D chest was no joke.

So we did prom stuff. Lots of laughs and squeals from the ladies, food that seemed "fancier" than what we got at home, DJs and congratulations of the graduating class, then lots and lots of dancing.

I was pretty sure that Jim would be down for a threesome proposal when he asked Cindy for a dancing, looking at me for approval. They were thick as thieves on the dance floor, holding each other close and whispering to each other during slow dance after slow dance.

Eventually, faster songs started playing and Cindy approach me at the table. "We need to go upstairs. Now," she implored me. So we headed towards the elevators, me with room key in hand (this is long before keycards and whatever else hotels have these days), and we got into the room. She had stashed our clothing changes, along with her sexy lingerie and heels, in her extremely large hand bag. She asked me if I wanted to wait for her (30 minutes) or maybe I would give her time to get ready -- in her lingerie and heels.

I decided to change out of my tux and hit the hotel lobby. And there I saw Jim. He was kind of slumped in a chair, and staring into space. I assume that he saw us leave the venue and knew what was about to take place. I plopped down in a chair across from him, and I thought that his jaw was going to crack itself on the concrete floor.

I didn't have a great way of communicating when I was 19 years old, but I succinctly told him that he was welcome to join us upstairs, that no meant no, that we called the shots, and if either or both of us told him to leave -- that the night would be over immediately. He asked if Cindy knew, and I told him that she didn't, but that she probably would be game for it.

I wasn't surprised that he joined me in the elevator. He was practically shaking with excitement.

I worked the key into the door of the hotel room slowly and deliberately. Cindy was probably in the bathroom freshening up and changing. I wanted this all to be a surprise.

I started stripping out of clothes immediately. Jim looked at me in a surprised way. I told him in a whisper that he needs to do the same, or maybe he needs to go.

When the bathroom door opened, Cindy did a quick spin. Her teddy was sheer and black, and had a thong back. Plus her black stiletto heels brought it all together. She did a quick spin while narrating what she was wearing -- before coming to full stop when she realized that there was not one man in the room, her boyfriend, but rather two men: her boyfriend *and* her ex-boyfriend, and we were wearing nothing but hardons and smiles.

She just kind of stared at us for a moment, then I approached her first, and we shared a lovely french kiss. I motioned to Jim to who french kissed her as well. We kept alternating back and forth with kissing Cindy, and clearly she was loving it. Her teddy wasn't long for this world. Kisses on the mouth led to alternating neck kisses and of enjoy her tasty gumdrop nipples.

After her crotch-snap teddy fell to the floor, I guided her over to the bed, she wearing nothing but heels, and started going down on her. Jim, to my surprise, aligned his cock to her mouth at the front of the bed, and I'd tell him periodically that we needed to switch.

I mounted Cindy first and threw her heel-clad legs over my shoulders. She would always moan a little bit in bed, but this time she was loud, like really, *really* loud. I told Jim that it was time to switch. He was more than happy to go down on her for a bit before taking her himself, she locking her legs around his waist.

I absolutely loved watching this. I pulled my cock out of her mouth and just enjoyed the action. Eventually they kissed as he fucked her, and he manipulated their positions a few times, finally ending up in doggy style, with my cock in Cindy's mouth.

The weird thing was that I kept feeling like I had to cum, and couldn't wait to cum, but my 19 year old body would not oblige. It was weird, but I was enjoying it all still.

And finally it happened, for the first time. "Oh my god, I'm close!" Jim cried out. "Where should I? ..."

"In me! In me!" Cindy cried out.

Jim let out a series of loud groans and his piston action increased in velocity before finally making a guttural noise -- and slowing down his thrusts until there was an audible sound of him popping out of Cindy. I didn't pay attention to it at the time, but Cindy had cum as well. The comforter on the bed had a pool of slick, clear substance on it.

I took Cindy from behind after Jim laid beside her for a rest. I kept replaying the mental images of my girlfriend being railed by her ex-boyfriend, and this is the first time that I felt the warm lubrication of a man's cum in a pussy. Finally I shot a tremendous rope into Cindy, and the three of us laid side by side in the bed, giggling to ourselves a bit, and saying nothing in particular.

After maybe 30 minutes, Jim initiated with Cindy. I had kind of dozed off for a bit, but I caught them kissing and fondling each other. Jim was in Cindy's mouth again, so I took this as an invitation to get myself back in the game, but this time I was going upstairs. I lubed up my cock and her asshole with my finger, and slowly entered her. That's when she got really loud, and Jim was alarmed enough that he looked at me with wide eyes.

"Guess where I am right now?" I asked him bluntly.

"Oh my god, you're up her chute!" he responded in shock.

I delivered my first load up her ass before taking a break myself. Jim was absoluted fascinated with the cum that was running out of her ass and started licking it up -- before he fucked her again, cumming in her for a second time.

We all dozed off again, but when I woke up, Jim was gone and I heard water running in the bathroom. I pretended that I was asleep, so Cindy started jerking me and playing with my nipples, getting me rock hard again before mounting me, telling me, "I took the sponge out. I want you to knock me up."

We fucked and fucked for the next 3 hours, in every position imaginable. I came twice more, but in the end it was just pure passion and excitement. I didn't cum the last two times.

We got a "good morning wakeup call" at 5am. We gathered our stuff after rounds in the bathroom, and I dropped her off at her parents by 6am. Sure, we broke up later in the summer, but from that moment on I realized that at times I was very much into extracurriculars in a relationship, where you add someone else to the bedroom on occasion.