Shape

Curious Couple Threesome

We were in our senior year of high school when Vanessa and I decided to have our first threesome. We were already in a serious relationship for two years, so we had been pretty comfortable with each other. I really respected her and decided that I wanted to take things slowly with her, so it took around an entire year for us to first have sex. All the while, she didn’t seem to care whether we moved slowly or not. After the first week of dating she had given me the first blowjob I’d ever received, and she’d ever given. Granted, it was slobbery, and I didn’t cum, she became a master of the blowjob all within a year. It got to the point where her even mentioning the possibility of sucking my dick would make me cum. She had complete sexual control over me.

Once we passed the sex boundary, I was always interested in what she proposed we do to spice things up. First, we started with bondage. She ordered a ball gag, whip, and handcuffs on Amazon Prime. The next day they came, we were balls deep (quite literally) in all 50 shades of grey. It even got to the point where she’d tie me up and dominate me, and I won’t lie and say I didn’t enjoy seeing her so sexy and powerful. Then, we went through a long period of roleplay.

This is where I really started to see the kinky side to her personality that I had not really known so well – she had managed to hide it from me for over a year. We’d set up scenarios where I was the teacher punishing her as the student, or where I was her step-brother who she wanted to sleep with so badly once the parents were out of town. It intensified to the point where she wanted me to play a prison guard who abused a prisoner – things got a little out of hand and kinkier than I could’ve expected – but I was still interested in it because I wanted to keep things exciting.

She was always initiating these explorations and I would match her level of willingness. It was only once Vanessa mentioned the threesome that I began to have some doubts about wanting to venture out on the next sexual expedition with her. As soon as she mentioned the possibility, tons of questions popped into my head: was it a girl or a guy, did she know this person previously, was this person clean, was I too boring for her to sleep with alone? Honestly, some insecurities hit, but thankfully, we communicated fairly well with one another, so I expressed my concerns. The day after she had mentioned it, Vanessa and I were hanging out at my house when I decided to tell her how I felt. 

“So, you want to have a threesome? Is it a girl or a guy?” I said.

“Um… don’t be mad. But it’s a guy,” she caressed my arm and giggled.

She was always so sweet and convincing, I could never flat-out say no to her. “I mean, I was hoping you wouldn’t say it’s a guy, you know I can get a little insecure if someone else is touching you too.”

“I know, I know. It’s completely understandable how you could feel this way. I just wanted something new and stimulating. Something where I’d feel the most pleasure possible, and a girl really wouldn’t do that for me. I honestly think you’d like it, and you wouldn’t even have to touch the guy if you don’t want. Just the fact that it’s making me feel good, might actually make you feel good too.” She said convincingly.

“Okay, babe. I’ll think about it. Maybe I could be chill with that,” I said.

I thought about what she had said for a few days, and for some odd reason I started to feel way more comfortable with the idea of another man fucking her. In fact, there were nights where I’d actually fantasize about it. There was this weird thing that she did where her suggestions would manage to seep into my mind, and I’d start to believe that they would be beneficial to me as well. Vanessa was so sweet, yet sexually devious and kinky, and no matter what, I always wanted her to feel pleasure, but now I felt like I had an opportunity for myself as well here.

It got to the point where I even decided upon the type of guy that I ideally wanted to fuck her. After a lot of soul-searching and making lists of qualities that I was looking for, I came up with the ideal guy. This guy had to be muscular (but slim), tall, intelligent to the point where he could hold a conversation, sensitive, have social awareness, and most importantly… have a massive cock. I started to feel how a girl would feel if she was crafting her prince charming, but in this case the prince charming would be someone who rammed my girlfriend so hard that it sent her to another dimension. It’s just that in my mind I thought that this type of guy would give Vanessa the most pleasure, and the more pleasure she received, the more I’d be able to enjoy the experience too.

It had now been nearly a week since our conversation about the threesome and Vanessa had not brought it up again, probably thinking that I just wasn’t interested. She hadn’t even tried to suggest anything, and I loved her for respecting me as well while she was under the assumption that I had my own reservations. It was a Friday afternoon and we were driving in my car on the way to the mall. Vanessa needed to pick up some new bras and I needed to buy some new tank-tops for the summer. We were silent in the car, although music was blasting. I lowered the music and put my hand on Vanessa’s soft thigh. I looked at her and she looked into my eyes and smiled. Her ocean-blue eyes won me over every time I looked at her and got lost in that sea.

“So, I’ve been thinking about what you said… a lot actually,” I said to her with a smirk on my face.

“What do you mean?” She was confused.

“You know, about having the threesome,” I smoothly said.

“We really don’t have to do it. I want you to be comfortable babe! And if you’re not, then I don’t want to do it,” she said so cutely. I could tell through her eyes that she was serious.

“I want to do it,” I said, as Vanessa got silent.

Now I could see the gears shifting in her mind. She was excited, but I could already tell what was going to happen here. Vanessa would think that I was only saying this because I wanted her to be happy and then she would feel guilty about the whole thing. But I was firm and knew exactly what I wanted, and I didn’t want her to feel that way either.

“No, I’m serious. I really want to do this. I’ve actually been thinking about it a lot,” I said.

“Can I be honest with you? I’ve been thinking about it too,” she said with an unsure look.

“Well I’ve been thinking about it so much, that I’ve actually picked out the exact type of guy that I’d want to do it with us. I tried thinking about the things you’d want to, and the more you’re enjoying yourself, honestly, the more I’ll enjoy it too.” I said now with confidence. 

This was a pivotal moment in our relationship. For the first time it was me taking some sort of initiative into the sexual exploration, and I could visibly see how it affected Vanessa. She started to fidget in the car a little bit, she was getting hot and bothered. Then, I explained to her exactly the type of guy that I thought would be perfect for us to do it with. Although she tried her best to hide her excitement, I could see her trying to catch her breath a little bit and her nipples hardened a bit through her tank top. She slid her hand along my leg and closer in towards my crotch. She could feel that I was rock-hard as I was describing the situation to her. This was her own confirmation that I was being completely honest about everything. 

“Alright. Then I guess we’re gonna do it! How’s tomorrow?” she said.

“Tomorrow? I’m so down. But how would we find someone in such a short amount of time?” I said.

“I don’t think you get it, Justin. As a girl, if I told any guy that I wanted to have a threesome with no strings attached, they would jump at the opportunity. Plus, based on what you described you’re looking for, I have someone in mind, baby.” She was as confident about this as could be.

“Who were you thinking?” I said. I could feel the anticipation building my body as I realized that we were actually going to be doing this.

“Julian from chemistry. Remember him? He’s on the football team, maybe like 6’3”, and I actually heard from some other girls around school that he’s hung like a horse.” She said while laughing and biting her lip.

“I remember him. That’s perfect” I said.

I felt my cock pulsating in my pants just hearing her get excited about it. I wanted Julian to own Vanessa more than I ever could. The thought of someone else taking control over her really got me horny. That entire drive was difficult because I didn’t want to seem too eager and excited, but I couldn’t wait for that next day. Even while we were at the mall, it was all I could think about – Julian’s large hands gripping Vanessa’s ass, slapping her silly. I don’t even know why this was so attractive to me, maybe it was a bit strange, but either way, it’s what I really wanted. 

Finally, it was 7:30pm on Saturday, and Vanessa was on her way to go pick up Julian from his house. My parents were away for the weekend, so we had the house all to ourselves. While she was gone, I was cleaning my bedroom by moving clothes into a closet, spraying some air freshener, and making the bed with clean sheets and a new blanket. I wanted everyone to be comfortable with what we were about to be doing, although I was honestly a bit nervous myself. I don’t know why, but I even took a bottle of red wine from downstairs and 3 wine glasses because I thought that it might be a good idea to get a bit drunk before doing all of this. 

As soon as I finished cleaning the room, I could see the bright beams of the headlights from Vanessa’s car hit my window as she pulled into the driveway. I heard her park and turn off the car. Then her and Julian walked up to the front door and rang the doorbell. I could hear them talking, making small talk. I took one last look at myself in the mirror, dressed in jeans and a sweater, and ran downstairs. I opened up the door and saw Julian and Vanessa standing next to each other – Julian looked a bit nervous. But boy, she wasn’t kidding, he was even more muscular than I remembered – I felt my heart sink just thinking about what was about to happen.

“Hey guys! I was just cleaning a bit, but I think we’re good to go” I said. 

“Dope,” said Julian as he walked inside behind Vanessa, “want to just get straight to it, or chill for a little bit?”

Vanessa interjected, “I think maybe we should get straight to it, try to break any awkwardness and get comfortable with one another right away.”

“That works,” I said.

Then, we all walked upstairs and went into my bedroom. Since it was pretty visible that we were all starting to get nervous I popped out the wine and poured glasses for everyone. Vanessa wasn’t giving me much attention, which was fine, because I know that she was trying to make sure that Julian wouldn’t back out at the last second. She sat next to him as they drank wine, and I leaned on my dresser across from them, drinking mine. Vanessa was casually talking to him about a chemistry test that was coming up, and as they burned through the wine, everyone started to open up. 

Once one bottle was finished, I’d go back downstairs and grab another. We were 3 bottles in and all of us were beginning to lose our inhibitions. We all sat on the bed laughing, and quite honestly, I don’t even remember what we were laughing about –nothing of any true importance. As Vanessa laughed, I noticed her rub her hand down Julian’s shoulder, feeling for his large, hard muscles. Immediately I was turned on and wanted to start doing what we were actually there to do – fuck violently. 

There was really no smooth transition into this, so I just started by putting my hand on Vanessa’s face and kissing her. I could taste the alcohol on her lips. I started to bite them. Then I cupped my other hand on her breast and started grabbing it softly, then a little more aggressively. Julian sat there looking at us, and out of the corner of my eye I could see that he wanted to get involved too. He was itching for Vanessa’s beautiful body just as much as me… and I welcomed it. I put my hand on Julian’s back and brought him in closer to Vanessa, who was in between us. Then, I guided his hand to her other breast, and he grabbed it and started rubbing, 

As I continued to interlock lips with Vanessa, Julian made his way over to her neck with his mouth. He started licking and sucking her neck, and I could feel Vanessa squirming with pleasure. She couldn’t contain herself. She took off her shirt, and then her bra. Although it’s not sexual, one of the hottest things I’ve ever experienced was her ripping off my shirt, and then ripping off Julian’s, revealing his perfectly shaped muscles. Vanessa stared at his body in awe (so did I) and then manically began to lick his chest and abs. The freak in her was coming out. I could feel myself getting hard. And Vanessa could too. She took her hand over my pants and grabbed my cock, stroking it up and down against my jeans. 

I couldn’t contain myself, so I tore my pants off and sat there in my underwear as Vanessa gave me an over-the-pants hand job and Julian started kissing her. She was trying to please us both, and she was doing a damn good job. Then, Vanessa moved fully onto the bed against the bed-post, and I followed. Julian stood up and slipped his sweatpants off. I could see a long, hard, and thick bulge underneath his boxer-briefs, just waiting to come out. He came down onto the bed and started to take off Vanessa’s bra. She helped him and then threw it off to the side of the bed. Julian and I laid on both sides of her, each licking and sucking her nipple. I had never felt her nipple get this hard. At that moment, I think I pre-came in my boxers, excited for what was to come. 

Now Julian was rubbing Vanessa’s leg and helped guide her leggings off of her. I liked that this new force was taking control of Vanessa. All of us laid down next to each other on the bed in just our underwear. Vanessa ripped mine off like a hungry animal and started to suck my cock. Her warm, wet lips on my shaft was a feeling I’d never forget as Julian watched and pulled off his own boxers. WOW. Vanessa was not wrong at all. He was hung, and thick. He must’ve been nearly 9” long – I had never seen a cock that big in person. And Vanessa still had not turned around to see. He started to stroke it with two hands because it was too big to do with only one. I wouldn’t say I’m a small guy, around 6”, but I was astounded. After getting himself even harder, Julian rubbed Vanessa’s pussy firmly over her thong. 

Vanessa moaned and I could feel her sucking even harder on me. She started to stroke me too while sucking and would occasionally slap my cock against her tongue as she locked eyes with me. She wanted to see my face and how hot I thought all of this was. She whispered for me to get up, so I sat up on my knees, and she continued to suck. Then she stopped for a second, turned around to Julian, who was feeling her up, and whispered into his ear that she wanted him to fuck her. Behind her, Julian went to his pants, pulled out a magnum condom, and then rolled it up past his tip and shaft. Vanessa had still not seen his massive cock, but she was for sure about to feel it all, every inch of it.

Julian got back onto the bed on his knees behind Vanessa as she was on all fours. He firmly grabbed his hard cock, slid her thong to the side, and slowly slid it into her. After the first inch, she seemed fine, but after the ninth, she was so clearly shocked by the size, there was a visible expression of pain and pleasure on her face. Nonetheless, she continues to suck my cock, harder and harder, I could feel her trying to suck me try, suck every ounce of cum out of my body. Her eyelids fluttered and she moaned loudly as Julian thrust into her slowly and meaningfully. I started to thrust into her at the same speed as Julian. 

Julian and I would match each other’s pace as we fucked Vanessa’s mouth and pussy. I looked at Vanessa and would see Julian out of the corner of my eye. Sweat poured down his chiseled body. I couldn’t help myself, so I put my hand on his shoulder and slid it down softly to his chest, just so I could feel muscles that hard and with so much definition. I got even harder and thrusted faster into Vanessa’s throat as she held my cock. Of course, Julian picked up his tempo too and put his hand on my chest.

All of our bodies being connected was one of the best feelings, and I couldn’t quite explain why. Having someone else there to please Vanessa was heavenly, and Julian had been exactly what I was looking for throughout the whole thing. All of our bodies were sweating, we were breathing heavily, Julian was grunting, and Vanessa was moaning. I knew the face Vanessa was making now, and I knew that it meant she was about to cum. This was faster than I’ve ever made her cum, but she didn’t want to cum that fast, so she took Julian’s cock out of her and told us to switch. 

She giggled as she stayed on all fours. As we switched spots and I pulled a bare skin condom from out of my dresser, I could see her pussy so wet and dripping. I couldn’t help but just go over to her for a second and lick it up before putting the condom on. When I was getting back onto the bed behind her and Julian was now in front of her, I heard Vanessa gasp.

“Oh my god. That’s so big. I didn’t know they actually got that big. Give it here,” she said to Julian.

Hearing those words struck a chord in my soul. It was incredibly hot that she was admiring Julian’s body, and knowing that she was satisfied and excited was more than anything I could’ve asked for. As I slid my pulsating cock inside of her, she grabbed Julian’s cock and started sucking it. The sounds of her sucking got louder as Julian thrusted into her, and we both thrusted slowly once again, slowly increasing in speed. Then, I heard Vanessa begin to make choking sounds on his cock. Despite these sounds, she continued to suck – she must’ve been enjoying that dominating feeling so much. Knowing that was happening gave me the urge to dominate Vanessa too and fuck her like an animal.

I brought my body close to hers, my sweaty chest against her back, and started sliding my warm, hard, and wet cock in and out of her wet pussy. Now on top of the choking sounds, she was moaning just as much as before. As I picked up the intensity, so did Julian. He thrust his long, fat cock into her mouth, and I heard the sounds of her choking get faster. It seemed like the room was getting hot and steamy while our bodies were radiating heat onto each other.

As I leaned onto Vanessa, I reached around her body and grabbed her breasts. As I grabbed them, I rubbed her hard nipples and bit my lips, trying to fit the urge to squeeze even harder and potentially hurt her. Now, Julian and I were thrusting as hard and fast as possible. I could feel Vanessa’s body begin to shake, and she was struggling to hold herself up on the bed. She lost her posture a little bit and we continued to fuck her. All three of us were experiencing pleasure like we never had before. 

Without a warning, Julian came in Vanessa’s mouth. He pulled her hair hard and clawed on his own chest. He knew how powerful he was and didn’t want to actually hurt Vanessa. There was so much cum, that I saw a lot of it fall out of her mouth and drip onto the bed. She continued to suck and swallowed the rest of his cum. Then she pulled his cock out of her mouth and licked the remaining cum off of the comforter. I slowed down the pace, focused on them. Now that was by far the hottest thing I’ve ever seen to this day. 

Next, it was our turn, and we had no say in the matter. I thrust into her harder than I ever had before. I could tell we were both thinking about how hot it was that we had Julian with us and that he had just cum a boat-load. Our bodies were in unison now, our eyes locked on Julian as he grabbed a tissue and cleaned up his cock. Now I pulled her hair from behind and still grabbed her breast as my cock fit fully inside of her. Vanessa shook again, her body convulsing at a million shocks a second. I couldn’t control myself either and I came harder than I ever have before. Immediately after I came, so did Vanessa. My condom was filled with more cum than could even fit, and I saw cum drip down from Vanessa’s pussy as I slid my cock out.

I told Julian to come over next to me. As he sat next to me and saw the cum dripping from Vanessa’s pussy, I told him that it was hers and that he should eat it up. Without hesitation, Julian got her closer to her dripping pussy and she turned around. He licked the leaking cum up in one long lick, and then ate the cum. 

“That was so fucking hot. We for sure have to do this again,” I said.

I couldn’t believe how comfortable I had gotten (regardless of being drunk) with the threesome and how it felt really good to get out of the zone of familiarity and into the realm of the unknown. This was the first time that we’d done this all together, and it definitely wouldn’t be the last.