Mystery Sex

[RocketRod]

I wonder if anyone had an experience like the one I had on my 21st birthday. First I'll introduce you to the ladies involved, with the names changed to protect the not-so-innocent:

Izzy - My girlfriend. Pretty, long dark hair, nice C cup tits. We had been dating a couple of years, and we both admitted that our love life was getting a little stale.

Hannah - Izzy's best friend and roommate. Dark curly hair. Incredible rack, probably a D. I would've slept with her in a minute if Izzy said it was OK, or maybe even if she didn't. (Hey, I was a 21 year old dude!)

Katie - Actual girl-next-door from when I was a kid. We used to bathe together, so she was practically my sister. In fact, since we went to the same college, my mom liked to ask if I had seen "my sister" lately. Of course, the idea of us dating or even hooking up seemed unimaginable. Oh yeah, you pervs probably want to know how she looked. Long brown hair, sweet face. She had smallish tits but a nice round ass. If she wasn't my "sister", I would say she was cute.

Now, on to the story. It was my 21st birthday and I had already told Izzy that I wanted to do something besides the cliched thing of going to a bar. Izzy told me to come by her and Hanna's apartment at 9pm. When I showed up I noticed Katie's car in front.

When I came in the three of them greeted me with big grins on their faces. They said me down at the kitchen table and told me about my present: I was going to go watch TV in the basement for a while, then at 9:30 I would go to Hannah's room. There would be a naked woman laying in her bed. I could have my way with her as long as I followed these rules:
1. The lights stayed off.
2. I used a condom.
3. After I was done I would go to Izzy's room and not leave for at least 15 minutes.
4. This was the biggie -- I would never, ever find it who it was.

This was pretty exciting and sexy, but I couldn't quite stomach the idea of not knowing who it was. I pointed out to them that for all I knew it could be a prostitute. They asked to me leave for a few minutes, and I could hear them whispering. Finally, they brought me back in and Izzy told me that it was one of the of the three of them, but I would never find out which one it was. Also, I couldn't touch whoever it was above the waist. This made sense, because as you can see from my description it would be easy to tell them apart from the hair and chest.

As Izzy was saying all this, I noticed Katie was bright red, clearly mortified that the possibility that I was about to do it with her was even on the table. I felt pretty sure it wasn't her, though. The only real possibility on my mind was that it was Hannah. Surely it wasn't Izzy, because fucking your own girlfriend with a condom, when we usually went bareback, would be a lameass birthday present.

Waiting in the basement, I was pretty excited about fucking Hannah. It was a shame that I wouldn't be able to lay a finger on those awesome tits. but you can't have everything.

At 9:30 I got up and went to Hannah's room. It was surprisingly dark, like they had boarded up the windows. I pulled open the blanket in excitement, reaching for where I thought her pussy would be. My hand brushed against what felt like a sweater, then I felt pubes. This gave me a hard-on right away, because I could tell it wasn't Izzy, who was clean shaven.

Without even taking my clothes off, I went down on her. She had a exotic taste, musky but also citrusy, that was totally different from Izzy's. "Oh, Hannah!" I said without thinking. She started softly moaning, then came hard. After she came she handed me a condom.

I got undressed quickly and put the condom on. Her pussy was shockingly tight. I remembered that Hannah had broken up with her boyfriend months before and had been celibate as far as I knew. Her pussy had some interesting ridges that I looked forward to exploring more. Honestly, though, I only lasted about a minute.

I could've gotten hard again, but I didn't have another condom. I asked the girl if she had one but there was no response. I went to Izzy's room. Looking at the pictures with me, I was happy that I had such an open-minded girlfriend.

When I left the house it was surprisingly quiet, but Katie's car was still in front. The next day I thanked Izzy for being such a sweetheart and letting me fuck Hannah. She laughed and asked, "What makes you so sure it was Hannah?" This made me wonder. Was it Katie all along? Was that why she was the one blushing? I'll probably never know.

Izzy and I broke up after we finished college. I still see Katie every few years, usually with my family, and always think about the fact that I may have been inside her.

[RocketRod]

A few months later I was at Izzy and Hannah's apartment when they had invited a friend who was getting ready to go out with a guy she really liked. The girl was a cute blonde, a bit on the thick side but not hard to look at. I was watching a movie in their basement when Izzy came down and said the friend wanted "a guy's opinion of her hair". At first I resisted because I was into the movie, but Izzy winked at me and said I definitely wanted to come up. When I walked into the bathroom, the girl's head was covered with a towel, which confused me for a second, then I realized she was totally bottomless with her big blonde bush sticking out!

I was stunned. She nervously asked if she needed to shave, then I blurted out that she looked "Great!" Then she smiled and gave me a hug. I could feel her tits against me which was a nice bonus.

Later Izzy told me that she had talked the girl into it because I confessed to her that I had never seen a woman with an unshaved blonde bush in the flesh. We broke up not longer after because we were graduating from college, so I think this was her last little present.