My First Threesome


The following story is a true account of the first threesome I had to the best of my memory. It is quite a bit longer than many of my other posts. Please leave feedback so I can improve myself as a writer. Enjoy.

As you might have read in some of my other stories Heather and I have a rather adventurous sex life. In the course of our discussions we both had expressed an interest in having a threesome. As one would expect, I wanted it with another girl and Heather wanted to try another guy. But I just dismissed it as just fantasy talk. It turns out we were a lot closer to reality than we ever thought. This is that story.

Heather and I have been broken up for a while now but we continue to hook up when we are both single and in the mood. Tonight is one of those nights. I drove into the city to Heather’s place and met up with her and her friend Jen at a bar down the block. We had a good night out and headed into Wrigleyville for some more drinking. On our way back Heather’s friend was on the phone talking with her boyfriend so Heather and I were talking as we walked behind her. We went up to Heather’s apartment to let Jen in so she would just go to bed already and stop annoying us.

“So do you want to spend the night?” Heather asked me while we were heading back down to my car.

“I dunno. I would like to, but you know Jen pisses me off. I really can’t stand her. She thinks she’s hot shit but she’s not.”

“Don’t worry Kevin, by the time we get your bag from the car and get back to my place she will be passed out on the couch. If you stay the night I will make it worth your while.” Heather said that last part with a sly smile as she playfully squeezed my ass.

“Well since you put it that way I don’t think that I can pass it up. We reached my car and I opened the trunk. Before I got my bag out Heather moved in and gave me a kiss. Holding me close she reached her hand down and traced the outline of my cock on my jeans. She whispered in my ear “I am going to have fun with this tonight.”

After I got my stuff we started walking back to her place. Holding hands we walked in silence for a minute before Heather broke it.

“Kevin, there is something that you should know. You know that guy Chris that I told you about?” I just nodded. Chris was a guy she told me she was kinda seeing. “Well Chris and I had a date last night. And afterwards we came back to my place and fooled around.”

This didn’t really surprise me any. I knew from what she told me that Chris was really into her, and I knew that she was physically attracted to him. Heather looked at me waiting to see what my reaction was.

“How far did you guys go last night?” It was a logical question for me to ask.

“We had sex.” Heather looked down at the ground; I could sense that she was ashamed to be taking another guy to bed less than 24 hours after her last. I squeezed her hand to reassure her that I wasn’t mad at all. We were no longer dating so I can’t be mad at her for going out and seeing someone else. In fact I was the complete opposite. I always encouraged her to meet new people and see what happens. I was always oddly turned on by hearing about things she had done in the past with other guys. I guess in a way I am somewhat of a voyeur.

“Was it any good?” I asked her.

“Yeah, I had a good time. He is so different from you the way he does things. With you there are more feelings involved, more caring and gentle. With Chris it’s more animalistic. We just go at it.”

“Were you two being safe while you did it?”

Heather hesitated a bit before she answered, “No, we didn’t use a condom. But he pulled out before he came. And I have been really good about taking my birth control pills.” Clearly Heather trusts Chris. It took me a while to be able to go without a condom even though we both hated them. I am glad to hear that he didn’t finish inside her though.

We had gotten to her apartment door when I paused for a minute. I pulled Heather close to me and gave her a hug. “I don’t mind that you hook up with guys you’re dating, I just ask that you are honest with me about it.” With that we kissed and then made our way into her apartment.

As Heather predicted Jen was passed out on the couch. This is one of those times where I hate that Heather has a studio apartment. The couch is directly across the room from her bed. So Jen was passed out about 10 feet away from where Heather and I were going to sleep. I went into the bathroom to change my clothes and put some shorts on for the night. By the time I got out Heather was already in bed under the covers. I slid in next to her and was surprised to find that she was already naked under those blankets.

“Kevie, I think you are a little overdressed.” With that gentle prodding I remove the remainder of my clothes and move in closer to Heather, pressing our naked bodies together. We started to make out a bit as our hands began to roam over each other’s naked body. My hand work their way down to her pussy and find quite a bit of heat emanating from it. As soon as I put a finger to it I can feel that she is soaking wet.

“I have been thinking about fucking you all night.” Heather’s hands move to my cock and find it semi-hard. She slides her body down under the covers and takes my somewhat limp cock into her mouth. I think she enjoys feeling me go from being soft to hard in her mouth. She is so good at sucking cock, something that I tell her all the time. While she is bringing my cock to life with her talented tongue her hands are gently fondling my balls. As my cock grows in her mouth Heather starts to let some of it go into her throat. Now that I am completely hard Heather starts to give me one of her amazing blowjobs. Her head starts off slowly, bobbing up and down on my pole. When she feels ready she takes me all the way in to the base of my cock and at the same time lets her fingers roam from my balls to my ass. As she deepthroats my hard cock she rubs around the outside of my asshole a bit. Heather must be a little more than tipsy because she is never that aggressive when it comes to my ass.

All of the sudden Heather pulls her mouth off of my cock and begins to crawl up the bed straddling me. As her head pokes out from under the cover she presses her lips against mine in a passionate kiss. Meanwhile her hand has a firm grasp on my cock as she guides it into her soaking wet pussy. She settles her weight onto me and my cock is instantly enveloped by the silky warmth of her pussy. I love the cowgirl position so much. I feel like I get so much deeper into Heather when she’s riding me like this. Heather starts to slowly move up and down on my cock and begins to whisper in my ear.

“I feel like such a slut. This is the second time I have had a bare cock in my in the last day. And one of my best friends is asleep on the couch right over there. Do you like fucking this dirty pussy?” All I could respond with was a groan. I wasn’t thinking anymore, all my focus was on how good her pussy felt around my penis.

“I know how much you like hearing about me having sex with other guys, so I’m going to tell you. Last night he came over here. We had a few drinks and were having a great time. There is never really much foreplay between us; it’s just a little making out, a little fingering, a little head, and then we fuck. So that is how things went last night as well. We were sitting on the couch and we kissed for a little while. Chris made fast work of getting my clothes off. In no time he was pinching my nipples and squeezing my breasts.”

“When he was ready to fuck he picked me up and tossed me onto the bed. I was lying right where you are right now, completely naked, watching Chris strip his clothes off. Do you like thinking about me being used like a little slut?”

“Oh yeah baby, I love hearing how dirty you are when I’m not around.”

“So I watched Chris take his clothes off and he crawled up onto the bed with me completely naked. His hard cock was hanging down as he approached. He is about the same length as you, and maybe a little bit thicker, but not too noticeably. He isn’t like you though; he just wants to stick it straight into my pussy. So I laid there with my legs spread and he slipped his hard cock into my wet pussy. Right away he started to really fuck me hard. There is no slow lovemaking with Chris, it is pure fucking. He grabs me by the ankles and spreads my legs wide as he pumps into my wet pussy. He likes to talk dirty to me too. He calls me a slut and asks how I like to get fucked. He tries to get me to try new things.”

“He said something to me that I know you will like. He asked me if I would ever have a threesome with him. Do you know what I told him? I said that if he found another woman I would do it. Does that turn you on?”

“I love that. You should get her number if you like her; bring her back for you and I.”

“Oh baby. I know how bad you want a threesome with me. I was never this naughty until I started dating you. Now I’m sleeping with two different guys at the same time and talking about having threesomes with both of them.”

“God Heather this is so hot. Your pussy is so wet. I am so turned on right now. If you keep going like this I’m going to fill your pussy with my cum.”

“You know what else Chris said to me? He said he would do a threesome with me and another guy. I told him I knew a guy. Do you want to do that? You wanna fuck me at the same time as another guy?”

That was enough to put me over the edge. I grabbed onto Heather’s ass and pulled her close as I filled her pussy with my hot cum. Heather moaned deeply into my ear as pulse after pulse of my cum coated the inside of her pussy. We lay like that on the bed until my cock softened enough to get pushed out of Heather’s tight vagina.

Heather rolled off of me and said “that was amazing” before she nestled her naked body against mine and we both drifted off to sleep. At some point during the night we woke up to slip our underwear back on. We wouldn’t want Jen waking up and seeing us sleeping there naked.

Jen must have left early in the morning because I was awoken by Heather’s lips being wrapped around my cock. When I started to stir she looked up at me and said “good morning hunny. You were laying there so peacefully with your morning wood that I had to take care of it for you.”

I smiled as I looked down at her as she licked the head of my cock like a lollipop. “That’s all right. You can wake me up like this anytime.”

“Well then you should just lay back and enjoy this.” Nothing else was said as Heather explored my cock with her mouth. She held my cock in her left hand as she licked from top to bottom all the way around my cock. While she was making her way around my shaft her right hand was gently caressing my balls.

Once Heather worked her way around my cock she took the head into her mouth. With a firm combination of sucking and flicking the head with her tongue Heather really gets me going. She starts to move my cock in and out of her mouth as she continues to massage my balls. Soon enough she is taking my cock deep enough into her mouth that she starts to gag a little, but that doesn’t stop her. After a few minutes of her expert cocksucking I find myself on the verge of cumming. I warn Heather that I am about to blow and she keeps on going. My entire body tenses up as I release my seed into Heather’s waiting mouth. She swallows it all down hungrily before she moves up my body. Lying next to me she gives me a kiss and I can still taste a bit of saltiness on her lips.

“So I wanted to ask you about last night. You know how I said that Chris would be open to a threesome? Would you really be interested in doing one with me and him?”

“Yeah I would definitely do that. Do you think that would actually happen?”

“Maybe.” The rest of our conversation was benign and I left shortly thereafter. On the drive home I thought about the last day and wondered if anything would ever actually happen. I didn’t put much stock into it, we have had this conversation before and nothing ever materialized.

Its a few weeks later and tonight is New Years Eve. I am at a fancy party with some friends and Heather is spending the night with Chris. They were going out to a dogtrack with Heather’s family and then heading back to her place. Things were going along great at my party. I knew that Heather was planning on getting some action tonight, and honestly I was jealous because odds are I wasn’t.

Heather and I were sending texts back and forth for a good part of the night. It seemed as though they were having a good time and the night was starting to wind down.

A little while later I got a text from her that made my heart race.

Heather: Hey its Chris… you need to get down here and fuck Heather with me sometime… double pen sounds fun… bring a girl

My mouth went dry for a minute; I couldn’t believe what I was reading. Not only was Heather into the idea of a threesome but her guy seemed to be into it too. I typed out my response:

Kevin: Ill do it one of these days. And if I had a girl for it we would have done it already.

Heather: No worries. Let’s just make it happen

Kevin: Don’t do anything I wouldn’t do…haha. I don’t know how that limits you though.

Heather: Don’t worry. I won’t corrupt her. Want a pic?

Kevin: Sure.

I didn’t hear from Heather for a while. But then about twenty minutes before midnight I got a call from Heather’s phone. It was too loud at the party for me to hear so I just let it go to voicemail. I went upstairs to listen to it in one of the more quiet bedrooms. It was a long voicemail, almost 3 minutes long. What could Heather have to say that would take that long to get out? I listened to the voicemail in anticipation….I wondered if she really called me while they were doing it, because that would be hot. I heard her saying goodbye to someone; it must be her sister and her boyfriend. Then I hear the sound of shoes walking on her hardwood floors and a murmur of voices. I thought that I heard the sounds of kissing but then the recording stopped. I guess her purse must have dialed her phone on accident.

Midnight came and went. There were toasts of champaign, hugs and kisses to go around, and phone calls to loved ones. And yet I hadn’t heard back from Heather yet. They must be having one hell of a time.

About quarter after midnight I received a text from Heather.

Heather: Happy Halloween!!! What a goofball.

Kevin: Happy Halloween! What did you dress up as?

Heather: A dirty little girl. My costume is my birthday suit.

Kevin: Hope you’re having a good night.

Heather: Awesome night.

Kevin: What are you up to?

Heather: Sucking dick.

Kevin: Oh really? You are good at that.

The next message I received blew me away. I had to go to the bathroom for privacy to look at it closely. Heather had sent me a picture message. I could tell that Chris took the picture. He was lying back on the bed and Heather was framed in the picture on her hands and knees. I could see the dark black bush of Chris’s pubes. Heather was on her knees with her arms supporting her upper body on the outside of Chris’s legs. His hard cock was in the center of the frame, with Heather’s lips wrapped around the head and a little bit of the shaft. He looked to be about the same length as I am, about 6 inches, and maybe a little thicker but not by much. Her eyes were looking up at the camera. I can see her tits hanging down behind the cock. The picture amazes me. This is one of the hottest sights I have ever seen.

Kevin: Wow, that’s nice. You going to fuck her too?

Heather: Did that once already, working on another.

Kevin: Have fun. Fill her pussy with cum.

That was the last message that I got from Heather that night. The next day I talked with Heather and she gave me all the juicy details. They did in fact fool around twice that night, though no cum ended up in her pussy. He was too nervous about it so he just shot on her back. She didn’t know about most of the text messages that were going back and forth, it was all Chris and I. And it also seems as though Chris was serious about having a threesome. They had talked about it quite a bit at one point during the night. Maybe this has a chance of happening after all.

To be continued…