A Surprise for the Both of Us

My girlfriend Sophie and I have been together for almost two years. Sophie is 19, attending university with somewhat of a bookish and innocent look to her. She stands 5’4” with a small build to match and curly brown hair complimented with bright green eyes. To top it all off, she has perfect breasts, nothing more than a handful – yet firm. Her nipples are pink, almost non-existent against her skin, but very noticeable when she’s turned on as they harden and stick out to such a size you can’t help but want to suck on them.

I’m Jeff, 35 and work at a local corporation. I’m just over 6’ with brown hair and brown eyes. I have a rather strong broad build, which has been found to intimidating to some.
Despite the large age difference between us, we have quite a lot in common. We have similar personalities and both enjoy sex. Granted I’ve had a few more years of experience than she has, but she’s into more of the ‘kinkier’ things, which balances it out. The most ‘risqué’ thing I’ve ever done is bondage and the like. However that’s not to say I’m a prude, it’s just that none of my partners have ever been interested in my fantasies. Like all guys, making two women cum for me at the same time is among my top fantasies. Doing it in a park or somewhere else public is a great idea too. To fuck a teenager would be hot as well, but I guess I could say I’ve done that; after all I met Sophie when she was just 17. However, by teenager I mean a few years younger than that; 17 is so close to legal, it doesn’t really count.

Sophie is great, because she’s into all that, even more actually. Her favorite fantasy is to watch (and play with) me fucking another man. She also loves being spanked and, like me, enjoys the “Daddy/Daughter” role-playing. But let me get to the point of the story, her favorite fantasy. I can’t say I’ve ever thought of fucking another man, sure I’ve been curious about what it would be like to suck a cock (mostly to see why Sophie loves doing it so much – she really is a great cum slut!) Sometimes I feel weird when she talks about me being fucked up the ass by somebody, I haven’t even let her use toys on me in that way, yet. Sometimes it makes me a little uncomfortable when she’s talking about her fantasy altogether; I think, I’m not gay and I don’t want people to think I’m even bi. She says I wouldn’t be gay; I’m not dating guys and if I’m bi even better, there is nothing wrong with it (or being gay either, but if I were gay I couldn’t have a relationship with her.) Besides, it’s not as if anyone has to know that I enjoy the touch of another man, except her and the other guy. I suppose she is right, but it’s a little weird for me, it’s something new. However, I said I would be open to anything and I love her so much that I want to make her happy the way she makes me happy.

Finally, I can tell you the good stuff, the purpose of all these words. Like I said, I wanted to make Sophie happy, so I figured she enjoys sex so much, I’ll make her fantasy become reality. I have an intern at work, Drew; he’s a good kid, just a year older than Sophie is. He has brown spiky hair, blue eyes, about 6’3 and an athletic build. He’s a smart looking kid, but also happens to be gay. I believe it important to set up a rapport with those I work with, so after he was with me for a week, I asked him if he’d like to come to the bar with me so I can get to know him without the stresses of a work environment. He accepted and we got talking, I asked him if he had a girlfriend, and that’s when he told me he was gay. It by no means bothered me, but he must have thought it did, because I was just looking at him silently and he asked “Is that okay?” I said of course, but really I was thinking; “I wonder if he’d be open to playing with Sophie and I?” Of course I wasn’t about to ask him then, after all I’ve only known him a week. Drew is a good kid, smart and a quick learner, funny when he’s not working, but serious when the time calls.

About a month after Drew was working for me, we were in my office – him filing and I behind my desk – and I asked if he was seeing anyone. Lucky for Sophie and I, he wasn’t. We somehow got talking about Sophie and I, and our personal sex-life. I decided to take advantage of the situation and told him about her fantasy. I know she wouldn’t like me telling just anyone, but I figured if I didn’t tell him, there would be no chance of it happening. He seemed to be composed, not taken aback by it.

Your probably wondering why I would even bring it up and look to take for granted the situation when I was a little uncomfortable with the idea. Well, I have to admit that if I was ever to do this – and I wanted to, because I was curious and so I could make Sophie happy – he would be the one. He’s an attractive guy with a great personality.

After a few minutes of silence, he said, “Have you ever been with another man before?”

I was embarrassed for some reason that my answer was no, and blushed. “No, I can’t say that I have…What is it like…being with another man I mean?” I knew I was showing some submissive attitude in the way I asked, and I knew, being his boss, that was not a good thing, but I was hoping that he would disregard it.

“I’ve never been with a woman, so I don’t know the difference…but I like it.” He said with a laugh.