Where it happened: Moscow
Langauge: English
Sex: Male
Rating: 5
Category: Straight
This will be a long story, all of it true, although you can decide for yourself, and the names will be changed to protect the innocent.
The story starts 3 months after my 16th birthday, as I was starting Year 12 (11th Grade to all the Americans out there), I was just beginning my A levels and was praying for a girlfriend.
At the time, I was 6’3”, and 210 pounds, so quite a large guy. You would call me a nerd, but also a nice bloke. I was popular with everyone, but I chose not to socialise much. I didn’t, and still don’t smoke, drink, or do drugs. But I still had no girlfriend, but that was soon to change.
In my chemistry group, there were two hot girls that I couldn’t pick between, Emily and Holly. Both are 5’3”, and around 100 pounds, but with a key difference. Emily has just the right sized tits for her build, but Holly’s were huge, maybe 34DD! The other key person in this story was Dan, who is 5’7 and 140 pounds. He liked to think he was a player, but he too was a virgin, and we were good friends, often joking about how forward he was with them, and yet they ignored him.
In December of Year 12, I couldn’t take it anymore, so I decided to write one of them a love letter anonymously. In the end, I flipped a coin to choose the name on top. Holly it was. I posted the letter, both nervous and excited. I talked about how I admired her from afar, and that I loved her. I realise now it was just teenage hormones talking, but we all think we know it all. The next week, Holly came into school brandishing said letter, hoping that her admirer was at school. We had Chemistry that day, but I planned to tell Holly when we were alone, which would have happened the week after because of an assigned project. She read the letter aloud many times, and I played my part, being excited and guessing who the guy was. Then it happened…
The following Chemistry lesson, the day before I would confess to Holly, Dan stood up, walked over to Holly, and kissed her on the lips! He then naturally said he sent the letter. I was devastated, but I held my tongue, wanting to see Holly’s reaction. She was smitten, you could tell just by looking at her. That fucking bastard! We all cooed at their sudden relationship, and seeing her happy face caused great anger in me. I feigned congratulating Dan, but I was already planning ahead. Some of you might think I was a coward for not expressing my love more openly, but that’s the wonder of foresight.
I frequently went to Dan’s house over the Christmas holidays, and managed to place a webcam in his room. If I couldn’t date Holly, I would at least see her naked. Sure enough, when the webcam was retrieved in early January, the New Year proved to be very good, and not just for Dan. Watching Holly’s huge tits bouncing back and forth as Dan rode her doggystyle whilst moaning his name was not only sexually satisfying, but also infuriating, knowing that could have been me. As Dan’s best friend, he would always tell me everything, and Emily could see it made me uncomfortable. In February, see asked me what was wrong. But I told her nothing.
Nothing really happened until November of Year 13, when our teacher announced that we were travelling to Moscow in a month for a week to some convention. ‘Oddly’ enough, this filled me with dread, as the loving couple currently frenching would have a week in a fancy hotel, so I knew that me and Emily would get a lot more time together.
When we arrived in Moscow, it was -12 degrees Celsius outside, so we quickly made it to our hotel, and I ‘shared’ a room with Dan, except we all knew that it would be Emily whom I would be with. That first night was very awkward, and I offered to sleep on the couch, but she didn’t mind. Getting into bed with a girl who I still had a crush on was really weird. We started talking about how she was jealous of Holly and Dan but also annoyed about how Holly was only interested in Dan, and not her as a friend. I agreed with her on pretty much everything. Each time I spoke with her, I was trying to hide my erection. That’s how it was for the next three nights. I would spend some time masturbating in the bathroom, as well on my laptop, as I had brought a copy of Dan and Holly’s sex on a memory stick. Me and Emily found out a lot about each other, we were both virgins, and that she enjoyed voyeurism. I then decided that I would show her the memory stick with the video of Dan and Holly’s sex to her.
Emily was curious as to how I acquired such a tape, so I started at end and went back, reaching the time when I wrote the letter. She was very shocked,
“You mean their relationship started because of the love letter that you wrote!” she said.
“Indeed and there is still more to the story” I continued. Emily’s eyes opened wider. I told how that Holly was merely chosen by the flip of a coin.
“So who was the other girl Ben?” I responded by shuffling closer to her and planting a kiss on her sweet lips. We both held that one kiss there, both realising the meaning behind it. When I broke away, she turned bright red, obviously embarrassed that I loved her. She began to fidget, so I took her hands and said that it was up to her what happened from here, and that I didn’t care about how she reacted. She began by nervously kissing me again, but I put more force into the kiss, focusing on only her. We kissed for an eternity, my hands running through her shoulder length, smooth brown hair. Her hands wandered too, down my back, through my hair and touching my face. I broke away again, and began to suck on her neck very slowly. I got behind her, and my hands started to wander, my left got to her left breast, my right started to travel to her moistening vagina, and I began to finger, grope and suck on her neck all at the same time. It quickly proved too much for a girl who clearly doesn’t masturbate, and she came all over my right hand.
I moved my hand away and grabbed her right breast, both still encased in their jumper prison. I slowly used my teeth to undo the zip at the back, while still groping her breasts. I removed her jumper, promptly followed by her shirt. I began to kiss down her flat stomach, until I reached her jeans, now mildly wet, and smelling deeply of her. I slowly undid them while kissing Emily on the lips once more. Her hands began to move to my jumper, at which point she removed it, tossing it aside, and breaking the lamp on the bedside table, plunging us into darkness, but none of that mattered. I unclasped her bra, exposing her 34B tits. I went to work, sexually sucking them, and giving them the attention they deserved. By now Emily had got my underwear off, and was gently rubbing my dick. I pulled my mouth away from her tits and started to softly sing Il Divo’s ‘Every time I look at you’, which ironic seeing as it talks about sex in the dark, and she had just broken the lamp. It was quite funny, especially when I unintentionally hit a high note as Emily started to suck my dick. I will be truthful and say that there is nothing quite like your first blowjob. As Emily’s mouth rode my 6 inch dick like a bronco, I could have only lasted 20 seconds before I blew the load onto her chest, and began to rub it in, which she found very alluring.
We removed what little clothing was left on each other between kisses, and my now hard again dick awaited at her exposed entrance. I coated my dick with her juices, and began to push, watching her face contort and squirm. She was very tight, but she begged for more. I reached her hymen, and told her to brace herself. I destroyed it in one swift thrust, plunging my entire length into her. She screamed in agony, and I shut her up with a long, sweet kiss. I asked her if she wanted to stop, but she pleaded me to go on, wrapping her legs around my back, preventing my escape.
I slowly began to thrust into her, loving every feeling and sensation that two hot bodies rubbing against each other gave. I watched as her face slowly eased out of its pained expression, and she began to enjoy herself more, wanting me to go faster and rougher, but I kept up a slow and somewhat romantic pace, trying to last longer, and to tease her. She began to rhythmically rock with me, popping my dick out a few times, which was a bit awkward. To tease her further, I rubbed the underside of my dick against her pussy, which she says brought her to an intense orgasm. Her body began writhing around, which brought me to climax myself, shooting a second load on her chest, which I licked off her erect nipples. She unwrapped her legs, and we both just laid there, panting, and realising what had just occurred. I broke the silence,
‘Emily, will you be my girlfriend?’
She just laughed at me softly, answering me by starting to make out. In our frenzied, naked frenching, I groped her tits again, and I soon became hard once more. Emily noticed and started chuckling about how eager I was. I told her it’s not difficult to be eager with such a beautiful girl such as herself. She gave me a cheeky smile, and began to rub my dick once more. In seconds she was sucking it again. I told her we should try 69, to which she agreed. She got on top, and I was left with her untrimmed pussy in my face. I figured I might as well try, seeing as she is sucking me off. I’ll be honest, I did it, and I’m still not sure after all these years whether I enjoyed it. It was quite daunting, so I stuck my tongue in there and hoped for the best. Meanwhile, Emily was really going at my dick, causing my third orgasm of the night, which this time was a facial, all of it eventually swallowed. When she was finished, I got up and started to run a shower, and it wasn’t long before Emily came up behind and begged for more sex. So I fucked her doggystyle in the shower, grappling her tits as they went back and forth, which I find really sexy. I lasted much longer this time and I came in her pussy, but she wasn’t mad at all. She wanted my child. We both collapsed on the bed naked and fell into a deep sleep, both happy and content at our newfound love.
We didn’t have sex for the rest of the Moscow convention, but we certainly had some chemistry. We decided that our relationship would be put on hold until the end of Year 13, but we told everyone anyway. Dan looked at me happily, boldly ‘claiming’ he spent a week with Holly to get us together, but everyone knew that was bullshit. We left schools, all four of us to different universities, but that wasn’t the end…
I went to visit Dan 2 years later, just before I headed to Germany as part of my degree. I found his room, and knocked on the door. A girl opened the door, clearly naked under a sheet, telling me to ‘Fuck off!’ I saw Dan, naked, in the middle of sex with a different girl. I immediately ran out to my car, but I was stopped by Dan, who now had shorts on. He pleaded with me not to say anything.
“Ben, you can’t tell Holly, if you do our relationship…”
“Was a lie. I know you didn’t write that letter Dan! It was me! I wrote the letter, and you stole her from me!”
Dan looked utterly astonished, and I told him all that I had felt the last few years, that before I walked in on him, I would have forgiven him, because he made her happy. I took my phone out, ready to call Holly, but that wasn’t necessary. Holly was also in the car park, getting out of her car on a visit to Dan, and she heard EVERYTHING. She started slapping Dan, who made no effort to fight back, and just started sobbing. Holly apologised for everything, but I told her it wasn’t her fault. She even offered to have sex with me, but I told her no, because I was still dating Emily, whom I hadn’t fucked since Moscow, and that being disloyal to her was the worst thing I could do. That night, back in my room, I sent Holly a copy of their sex tape and the love letter, apologising for all I put her through…
So where are we all now? Well, me and Emily got married 5 years ago in Moscow, and have two wonderful kids, named Dan and Holly. Holly herself sank into depression and attempted suicide. She is currently with a new man, Jake, who was the other member of the old chemistry class. She is happy and announced her engagement. Dan on the other hand is unfortunately dead. His sleeping around got him HIV, which advanced to AIDS and slowly killed him. I was the only one there at his side when he died, and in his last moments, I forgave him. He simply smiled and passed on to the other side. I went to his funeral, and there I helped to lay him to rest. He was by no means a bad man, he just made bad choices.
I and Emily still have sex regularly, and I have lost weight as a result. I don’t regret anything that happened, but I wish Dan was around to see his godchildren.
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