A Surprise For The Both Of Us

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. I laughed too, but mostly because I felt a little dumb for asking him that.

“I take it you’ve thought of making your girlfriends’ fantasy come true?” He looked at me with a big grin. He did have a really nice smile.

I was dumbfounded; I didn’t know what to say. I was beginning to think I couldn’t do this after all. Perhaps, this fantasy should stay a fantasy. Then I thought of Sophie and regained the dominant personality I once exuded. I boldly said, “Yes, I have. I just need to find the right guy for it.” And I looked back at him with the same big grin. I decided I could reel him in without actually telling him I wanted him to be the guy for her fantasy. Maybe I’d enjoy this more if it were a game? After all, I’m a businessman; I’m just as competitive as the next guy is.

“I might know someone, but he’ll want to know if it really happen. Is this something you would actually do, or will you get scared off…just so he doesn’t leave with blue balls or something.” He stepped a little closer and smiled.

I thought about it, his smile, the vibe I felt from him, and knowing he wanted to fuck me; it all turned me on. “Well I’ve never been with another man, but if there were chemistry between us – me and the guy of course – then I would go all the way. I suppose I would have to meet him to find out first.” I was now smiling and open to whatever, right then and there.

He moved closer, standing next to my chair so I had to look up to him. He smiled and said, “What if it were me, do you see some kind of chemistry here with us?”

I put my hand on his thigh. My heart was beating so fast, but I managed to get out, “I wouldn’t want anyone else.”

Just then my secretary knocked on the door. “You have a call on line one.”

“Alright, thank you.” “You’d better get back to work too.” I said to Drew as I resumed a serious and professional face.

That night, I was thinking of Drew and what had happened in my office just several hours before. Recalling the feelings I had, I couldn’t help but be turned on again. I turned to Sophie who was reading and started kissing her neck. I knew she would be game. If she was reading, that meant she wasn’t tired and would most likely also be in the mood for love making so that she would become tired. I have to admit, I did think of Drew while we were having sex. I was surprised at how horny it made me. The idea of sucking his cock made me so hard, I fucked Sophie hard and fast with such stamina, it surprised us both, but in a good way!

The next day was so hectic with deadlines, Drew and I ended up having to eat our lunch quickly and in my office so we could save time that would otherwise be spent traveling around to where we usually ate lunch or ran errands.

“Have you told Sophie that her fantasy is going to come true?”

I almost choked on my sandwich. I didn’t expect the issue would be raised so quickly. “No, I don’t want her to know, I want it to be a surprise.”

“When do you want it to happen, a special occasion or out of the blue so it’s a true surprise?” He seemed so composed, so natural, like this is nothing new to him.

“I haven’t really thought that far ahead. Have you ever done something like this before? You seem to take this all with ease.”

“No, I’ve had sex with a couple guys, but never in front of a girl. It is just in front of her right? I’m not actually going to have sex with her am I? I’m not bi.”

I had never thought of that detail before, but I definitely was not going to allow her to fuck another man, be it he be straight or otherwise. Besides, she has never told me about fucking another man when talking about the fantasy. “No, you won’t be touching her, nor will she touch you.”

“So when do want to do it?”

“Um…Well she has a late class tonight, how about Saturday?” I admit, I was eager for it to happen rather quickly and since it was already Thursday, it would let me sleep on it another night, so I still have time to change my mind. “She works Saturday morning, babysitting her cousin, but if you come over around noon, you’ll get there shortly before she gets home.”

“Sounds good. Should I bring anything?”

If I were in a playful mood, I would have responded ‘Just your cock’, but seeing how I was stressed with work, I just said, “No, just yourself if good.”

That Saturday, I was cleaning up the house a bit when the doorbell rang. It was 11:50am so I knew it was Drew. When I opened the door, it was Drew standing there with khaki shorts to the knees, sandals and a white T-shirt. We must think alike; I was wearing blue shorts and a black T-shirt. We said our hellos and I let him in.

“Welcome to our place. Have a seat.” I motioned him to the couch in our living room. “Would you like a drink? I’m having a beer.”

“Beer sounds good, thanks.” He was looking around, customary for all visitors in any house who are there on their first visit.

I handed him the beer and sat next to him. We took a chug of our beer and were silent. Finally I broke the silence, “I admit, I’m a bit nervous, are you?”

“About as nervous as I get when I’m about to have sex. There’s always some sort of pressure, ya know?”

“Yeah.” I looked down at my beer and took another drink.

“Look, I can still leave if your not sure…she’s not here yet.” He sounded as if he were a little disappointed in case I agreed to that suggestion.

“No, I want to do this. It’s just that it’s new to me, besides, you work for me, that makes it a little uncomfortable in itself.”

“Yeah, that’s true. Here, maybe I can make you a little more comfortable so she can see how much you’re enjoying it, and see less nervousness in you.” I agreed.

He turned towards me, took my beer and put it on the coffee table.

“I promise you, by the end of the day, you’re going to wish you had been with a man sooner.”

That’s when he leaned over slowly and kissed me. I was shocked, but glad. It was a soft, quick kiss. Instinctively I leaned back into him and kissed him back, this time it was a little harder. I liked this. We kissed like that for a few seconds more and then I opened my mouth a bit. He did the same. I thrust my tongue inside his mouth, feeling his tongue massage mine back. It felt so good. Not any different than if I was kissing Sophie.

He pulled back, looked at me and smiled. “See not that bad, uh?”

“No. I liked it a lot, actually.” It was true, it made me want more, but I had to wait for Sophie.

As if on cue, Sophie came through the door. She was wearing a summer dress that came to just above her knees. She has always looked cute in a summer dress, if she wears one without a bra and the wind hits her just the right way, her nipples harden and show in the dress. Just thinking about it, makes me hard. “Hi sweetie.” She said as she put her bag on the hall table.

“Hey. Sophie, I’d like you to meet Drew. The intern I told you about.”

“Oh yes. Hello, nice to meet you.”

“Nice to meet you too. You’re right, she is stunning.” Did I mention he was a charmer!

“Wow and here I thought all corporate men were cold-hearted.” She winked and sat in the chair opposite us. We all laughed.

Once the laughing ended, the inevitable awkwardness ensued. Finally, I had to tell her why Drew was here, the sooner I tell her; the sooner we can begin. Granted it was still only shortly after noon, but I wanted this to last longer than just an hour.

“I suppose you are wondering why Drew is over?”

“Not really, I just assumed he was over for a beer. Male-bonding.” She paused for a second. She’s a smart girl. “That is it, isn’t it?” She was now very suspicious.

“Not exactly, well you got the male-bonding part right.” Drew and I couldn’t help but laugh at Drew’s corny joke.

Sophie was turning in her chair, I think she had caught on now, but the suspense was driving her crazy. I knew the last thing she wanted was for her suspicions to be just that, and not reality.

To show her she could relax and enjoy the moment, Drew leaned over and kissed me. The kiss was even better than before, knowing Sophie was over there with a big smile and probably starting to get her panties a little wet.

I wanted to drive her into frenzy, so I moved my hand over to his lap and started to caress his thigh. Drew moved his hand to the back of my neck. Followed by moving his hand down my back and under my T-shirt. The feeling of his hand over my skin and the thought of Sophie becoming horny, it was all too much and my cock started to stir in my shorts.

Drew and I moved closer together, our kissing becoming more and more intense. As our kissing became more intense, I wanted so much to feel his cock. I moved my hand up his thigh and started to rub his cock through his shorts, his body stiffened to my touch and his cock instantly grew. I’ve played with my own cock before, and this felt just as good, if not better. I couldn’t get over how much I liked this.

Sophie walked over to us and put her hand on my shoulder. “I think we should move to the bedroom where it’s more comfortable.” She read my mind. We broke off the kiss and walked up the steps to the bedroom.

Sophie was the first to undress. By the time Drew and I made it to the bedroom, her sundress was off and so was her bra. She had on a cute pink thong. Drew peeled off his shirt and shorts so quickly, that by the time I was finished admiring Sophie's naked body and turned to him, he was already naked.

His cock was semi-hard, but already it looked exceptional. It was already at a good 6 inches, thick, but nothing too intimidating. Mine is about 6 inches when fully erect, but very thick – so I’ve been told.

Sophie walked over to me, pressed her body to me. I could feel her hard nipples pushed against my chest. I kissed her with such passion. Man, I loved this girl so much. I felt Drew behind me, caressing my ass and rubbing my back. I pulled back from Sophie a bit, slipped off my shirt and shorts and resumed kissing her. I cupped a breast in my left hand, making her moan to my touch. I slipped my tongue to her neck and kissed her gently over her jugular and earlobe, just where she likes it. I moved my right hand down her stomach and to her panties. I could feel the warmth and the moisture from her pussy through the crotch of her panties.

Meanwhile, Drew was kissing the back of my neck and my back. He slipped his hand to my ass, caressing my cheeks. I naturally spread my legs a bit so he could get better access. He took the cue and slid his hand through the cheeks of my ass, teasing my asshole along the way, and cupped my balls gently. If I wasn’t completely hard then, I was now!

I slid a finger inside Sophie’s panties and teased her pussy lips with my finger. I did all I could to avoid her clit – which was hard to do considering her clit was sticking out quite a bit. Finally I pushed two fingers inside her pussy. She moaned so loud and her knees became so weak she almost fell to the ground. I pushed her to the bed and pumped my fingers inside of her, faster and faster, harder and harder. I could feel it wasn’t going to be long before she came. Her pussy was so wet, juices were spilling onto the bed, she was thrashing around, wanting more. She groaned, and I felt her cum, she shuddered and shook. I pulled my finger out and kissed her, she came so hard she was a little too weak for a big passionate kiss.

I kept kissing her face and her neck and Drew played with my balls and rubbed my cock from behind. Sophie got up and slid from underneath me. “I want to watch you two.” I wasn’t about to object. I moved over to Drew and kissed him once more, this time I could feel his cock push into my stomach. I pushed back against it. I reached down and grabbed his cock into my hand. It felt so good; I had to taste it. Without any hesitation, I moved to my knees and licked the precum from the head. Salty. Good. I moved the entire head into my mouth. Inch by inch I moved the cock into my mouth. I instinctively knew what to do – but I also learnt a bit from Sophie. I played with his balls while I moved the cock in and out of my mouth. He was moaning with such pleasure and praising my work. What a role reversal, I usually praise his work…come to think of it, I still have a chance to praise his work, a different kind of job.

Drew moved to the bed and lied down. I followed and took the cock into my mouth again; I didn’t want to stop. Sophie came up behind me and placed her head underneath me, between my legs. I felt her warm mouth cover the head of my cock. I moaned onto the hard cock that was in my mouth. Like a chain reaction, Drew moaned as well.

We moved in sync, the three of us, until Drew stopped us. He became the dominant one. He instructed me to turn away from him, but to remain on all fours. I knew what was coming. He positioned himself behind me and started to caress my ass. His finger slid between the cheeks and started to tickle my asshole. I moaned from the pleasure. Sophie was still underneath me sucking my cock, her pussy in front of my face. As Drew was applying pressure to my asshole with his finger, I brought my face to her pussy and licked her clit. She moaned onto my cock, sending shivers down my spine.

I felt more pressure on my asshole, and realized Drew was inserting his finger into my rectum. It didn’t hurt like I thought it would, it felt great. I pushed back, forcing his finger to go all the way in. He started moving his finger in and out, slowly at first, then quickening the pace. My body rocked along with his finger, creating a rhythm between the three of us.

He pulled his finger out and I felt even more pressure being pushed against my back door. I knew this was his cock. I started to have second thoughts. “Just relax, I’ll go slow.” He must have read my mind.

Sure enough, he pushed the head in slowly. It wasn’t too bad. He stopped for a second. “Are you okay?”

“Yes, don’t stop.” He pushed it in, slowly, inch by inch. It was a tight fit and hurt a little bit. I winced. Finally, he was all the way in. “Just relax.” I did.

He didn’t move for a couple seconds. I resume licking Sophie’s pussy, which was wet and tasted sweet. I’ve always loved licking her pussy.

He started thrusting in and out, slowly at first. It was a little painful, but the more he did it, the more I began to enjoy it. Soon enough, I was pushing back against his cock. “Fuck, that feels good. Pump faster.”

“Are you sure.”

“Fuck yes, just don’t stop!” He was pumping faster and harder. With the speed and pressure that Drew was using to fuck my ass, I was forced to lick Sophie’s clit just as hard and just as fast. I didn’t know if I could take it any longer. Sure enough, I couldn’t. My hot cum, was forced down Sophie’s throat; she took it all. Soon after I came, Sophie’s legs closed around my head and she came, spreading her juices onto my face. Drew was thrusting so hard now I knew he was about done. I was right. He pulled out and came on my ass cheeks and my back.

We lied in bed for a bit; catching our breaths and letting our bodies relax.



“I love you.”

“I love you too.”

“Hey, what about me?” Drew joked.

“We’ll definitely have to do this again, don’t you think.” Sophie asked. You could tell just by the way she said it, she was smiling.

“I think so.” I replied.

“Remember I told you that by the end of the day, you would have wished you did this sooner?”

“Yeah, you were right, but since I’m the boss, you’re not allowed to admit that I was wrong.” We all laughed and planned for when we would do this next.

What did you think of this story?