Jessica and I have been dating for a year now. She was perfect. She was a short and curvy blonde. Her golden hair ran down her back all the way to her lower back. Her 34D breasts really stood out as she only measured 5'2. She was really into fitness and had been squatting really heavy weights for years now, causing her ass to be really voluptuous compared to the rest of her small frame. Jess was definitely extremely sexy and I always considered myself lucky to be with her.
As for me, I'm Dylan. I'm not particularly tall, measuring 5'8 but I do have an athletic build. I've never been overly muscular but as a soccer player, I've developed some strong muscular legs and glutes. I've always kept my brown hair trimmed short and I was never able to grow much of a beard so I kept a clean shave.
We were the type of couple who was always open to new experiences. We've tried many things in the short time we've been dating like bungee jumping, rock-climbing, skydiving, parachuting and travelling to exotic places. We had an amazing sex life and we have been pretty vanilla up until now. As our relationship grew, we became more and more open to new things, starting with light BDSM such as bondage and edging, nothing crazy.
One night in the bedroom, Jessica had mentioned a fetish of hers which shocked me. She had confessed that she had fantasized about watching me have sex with another man. I was not even close to being gay and thought it was kind of a weird fantasy, but I respected Jess and did not judge her even thought I didn't see it becoming a reality.
As time went on, I noticed she was mentioning her fetish more and more. It was clearly something that greatly turned her on so I obliged and played along whenever we dirty talked. I never thought about actually having sex with a guy but seeing how much she got turned on fantasizing about a me sucking a dick or a guy fucking me was turning me on. I just loved seeing her turned on, and whenever we talked about that stuff, we would have amazing sex, so who am I to complain?
One thing we had never done as a couple was anal. She wasn't really interested in having anal sex and had joked that if I ever received anal from a guy, she would try it. I laughed at her for that ridiculous statement. That conversation got her thinking and she started by buying me a butt plug and having me try it out to see if I liked butt play. For her, it was a turn-on to see me insert something in my ass and imagine it was another guy.
Jessica's naughty side would come out intensively every time we'd talk about my butt being played with. The first time I tried a butt plug I wasn't sure I liked the feeling. There was a little bit of pain but then with patience and lube, I started enjoying it. I even started fucking Jess with the butt plug on and it made my orgasms even more intense. I had always been comfortable with my sexuality, and for me it was just an extra something for our sex life, nothing gay about a butt plug. Jessica was loving the fact that I liked having the butt plug in me.
After about a month of having sex on and off with the butt plug, Jessica had another surprise for me.
We had taken a cab to her place after a night of clubbing, since we were both a little drunk. She looked so hot in her skin tight dress barely covering her ass cheeks. Her breasts looked like they were going to rip open the top of her dress and it was such a turn on. We had been flirting and rubbing each other all night on the dance floor and I was really horny.
We started making out in her room and feeling each other up. I rubbed my hands all over her body, caressing her hips, squeezing her ass, fondling her breasts. I turned her back against me so I could push my hard dick up against her big ass while I unzipped her dress. Once her dress dropped down, I glided my hands towards her big breasts and started fondling them again, softly grazing her nipples. She let out a moan of pleasure and turned towards me to keep making out with me while she unbuttoned my jeans. She took my pants off and fell down to her knees and started kissing my thighs, moving her head up towards my dick. She kissed the head of my dick, then took my dick into her mouth. Jess gave amazing blowjobs and she had no issues deepthroating me. It felt amazing. She had her hands on my thighs as she was sucking my dick and started to guide them towards my ass. She started massaging my ass cheeks, I loved that. She looked up at me with a really naughty face while she glided her index and middle finger into her mouth, getting them wet and I knew what she was going to do. She slowly started rubbing my asshole with her two wet fingers, I'd be lying if I said I didn't enjoy the feeling. The month we had spent playing with the butt plug really got me into the butt play.
"You want me to finger your asshole baby?" She asked seductively.
"Oh yeah babe, do it, it feels sooo good." I answered submissively.
She started penetrating my asshole with her two wet fingers and I let out a moan. I had recently found out that I was loving giving up control, and having my ass played with made me extremely submissive.
After fingering my ass for a few minutes, she stopped and smiled at me. "I have a surprise for you, well it's actually it's more for me but I really want to do this." She went to the closet and pulled out a dildo attached to a strap-on.
At that moment, I was extremely horny and up for anything. I have had good practice with the butt plug and was pretty sure I could handle it. "Jesus, Jess. You are one naughty girl" I said with a small laughter I couldn't contain.
"I know Dylan, I just can't help it. I just get SO turned on when playing with your ass. What I really want to do is fuck you with the strap-on and imagine a guy is fucking you".
"Ok babe, if that's what you want, let's try it" and I laid on my back on the bed. I was ready to try this for her, but at the same time I was curious to see if I'd like it too.
Before putting the strap-on, she played with my dick some more and got me more and more horny. Once I was extremely hard, she hopped on top of me and slid my dick inside her soaking wet pussy. "Oh, fuck baby, your dick feels good" she said as she was riding me. After a few minutes of she added "I love how you're fucking me... but now I'm going to fuck you" she told me between her panting and moaning. Something about her being so turned on about wanting to fuck me and seeing me get fucked was an extremely hot scenario. I was really into her fantasy in the moment as well.
She started lubing up my ass, and inserted 1 finger at a time, adding another one until she could fit three fingers in. She was playing with my dick at the same time and it was feeling amazing. Once I was stretched out, and really horny she started putting on the harness. Something about her wearing a dildo, like if it was her dick was extremely sexy. The dildo looked average, similar to my dick, nothing scary looking, I was ready for this.
She lubed up her fake cock and started grazing my butthole with the head of the shaft. I noticed at that moment by the feeling that it was slightly bigger than my butt plug. As she started sliding her strap-on into me, Jess' face held no secrets. She was getting so much pleasure in seeing her dildo get absorbed by my asshole. I think seeing her pleasure was more of a turn on than getting pegged at that point. As she started pegging me, I did notice how good it was feeling. It didn't take long for me to want to cum soon.
"How's that baby?' she asked. "Do you like feeling a dick in your ass?
"Oh yeah Jess, this feels so good" I wasn't lying but I was playing along knowing that this was a huge turn on for her.
"I really want to see you get fucked like this by another man" she said
I didn't really know what to say, but in the moment, I was extremely horny and about to cum, so, I didn't think much of it and just answered: "Fuck yeah, that'd be hot baby". Slightly regretting my words after they came out of my mouth, but it was all play anyways.
"I want you to cum while I fuck your ass Dylan" she said as she grabbed my dick and started stroking it while fucking me faster.
"Oh shit!" the pleasure took me by surprise. The feeling of being stroked and pegged simultaneously was too much. "I'm going to cum!!" I started orgasming intensively as she was pounding my ass. So much cum was coming out of my dick and landing on my chest as Jess was fucking my ass mercilessly. Once I was done cumming, she stopped fucking my ass threw off the strap on and sat on my face.
"Make me cum baby" she said as she rubbed her soaked pussy on my mouth.
I started licking her with purpose. She was obviously extremely horny by the fact that she had fucked my ass and made me cum while fucking me. It only took about a minute before she came intensively, her body was shaking all over my face. It was hot as hell. That night we lay there and talked about how hot that was, and that was how we introduced pegging into our sex life. My ass was sore the first few times but I seemed to get used to it.
A couple months later, Jessica had invited a couple of people over to her place for a party. I was already there with her, helping out with the preparations. It wasn't going to be a big event, she had a couple of friends coming, her two best friends; Emily and Steph, and a couple friends from work. The party was great, we had a couple of games planned including silly drinking games, where most of us got drunk. The vibe was great where we just chatted about random stuff as a group, it was a lot of fun. Near the end of the night Emily and Steph were hanging out with Jess and I was hanging out with one of Jess' works friends, Billy. Billy was I.T support at Jessica's office and seemed like a really cool guy. We talked about hockey, work and I found out he had quite the funny drunk stories. After a while Emily and Steph left and it was only Jess, Billy and I.
Jess had already spoke a few times about her friend Billy from the office. She had described him as really good guy that everyone liked in the office. I'm sure he was popular with the ladies at work because I could tell he was a good-looking guy. He must have been around 6'2, really muscular, strong jawline, short jelled up black hair and dressed really well. I wasn't really jealous because Billy and Jessica seemed to have a very platonic relationship.
"It was cool to meet you tonight Billy, do you have a girlfriend? Next time we could do a double date!" I said in the midst of our conversation.
Jessica giggled and answered before Billy had the chance, "oh babe, Billy is gay, but he also doesn't have a boyfriend"
"Oh ok, cool!" I answered. As I responded, some mental connections were happening. There was a gay single guy in my living room with my girlfriend who had a fetish of watching me get fucked by a man. Was this planned or a funny coincidence? I laughed internally at the whole situation.
"So... on that subject..." Billy started, "Jess told me about her fetish and asked me if I was interested..."
There it was. I was speechless, Jess had told her colleague about her fetish about seeing me with another guy? I was so embarrassed I didn't know what to say.
"Relax dude, no pressure, we won't do anything you don't want to do. It felt like we hit it off though" he said.
He was right, I really enjoyed our conversations and it seemed like we could be good friends, but I was still confused on what was going on. I looked over at Jessica.
"You know how much this would turn me on if you did anything with Billy, I'm not going to force you or anything, but aren't you open to it?" she said.
"I mean... I don't know..." I answered trying to think about it. I was pretty drunk, and when I thought about it, I'd probably do it for Jess, as I know it was a really big fantasy of hers, but I didn't appreciate the pressure.
"Did you plan this all along Jess?" I asked, trying to get answers and stalling to figure out how I was feeling.
"Oh my god, no. It's just a funny coincidence and I kind of shared my fantasy with Billy in the kitchen earlier, and both of us being drunk we kind of thought it was a good idea..." she said not able to control some of her giggling. She probably noticed how crazy it sounded out loud.
"Again dude, no pressure. Jess told me you are a super open guy, so why not have fun? I'm really experienced with first-timers too actually." Billy said with a very calming tone. He seemed like a really mature guy.
"Well, I mean..." I was hesitating still.
"Why don't you two take off your pants and see what happens from there" Jess said, mischievously.
"No problem with that" Billy said and ripped his pants off. "Come on, Dyl, are you going to follow?"
I was kind of curious on what would happen and this sounded kind of fun. I knew Jess would really be turned on by anything from this point forward so I decided to go with the flow, I took off my pants and we were both down to our boxers.
Billy took hold of his boxers, "alright, on three..." Billy said with a huge smile. "One... two... three!" Billy and I removed our boxers and stared at each other's junk.
I had never really stared at another guy's dick before but when I saw Billy's dick, I knew it was a good-looking cock. It was definitely bigger than mine. I looked about an inch longer, and a bit thicker and the skin on it just looked good. I was a bit mesmerized for a few seconds and then snapped out of it when I heard Billy, "You like what you see?" he chuckled. I looked up to him, slightly embarrassed that I got caught staring and just managed to scoff, I didn't know what to say.
"You can keep looking at it if you want babe" said Jessica, obviously turned on. "No harm in that."
I looked back down, and it looked like it grew even more, Billy was excited.
"You know... my fantasy is to seduce straight boys like you and make them crave cock" he said seductively while walking towards me, with his big dick exposed.
I laughed nervously to Billy's silly statement. "Hah, well good look with that..." I said without being able to take my eyes off his dick. I was just impressed by the size of it and it actually looked like a really beautiful cock, part of me wished I could have such a nice big dick. I looked down and confirmed my dick didn't compare, but I was hard as rock and leaking precum.
"Someone's excited" Billy said with a mischievous smile. I was speechless. He was walking over and soon he was right in front of me, his dick a few inches from my own dick, both hard. It felt like I was in a dream and nothing of this was real.
"You can touch it if you're curious" Billy said reassuringly. It was true. I was curious and was becoming really interested in this experiment. I hesitated for a moment and decided to reach for it with my right hand. I grabbed it and it felt warm, thick and veiny. I quickly noticed that it filled up my hand and I could barely wrap my fingers around it, letting me know he was quite bigger than me. I instinctively started stroking it very slowly like if it was my own for some reason, Billy loved it. He moaned with pleasure, "oh yeah... that feels good." He said softly. I felt some kind of power being able to bring him pleasure so easily.
"Why don't you get on your knees to get a better look?" chimed in Jessica who was loving this scene. Her participation and interest in this were encouraging me to just do what she wanted. I wanted to give her that pleasure and fulfill her fantasies and at the same time I was really curious to see how far I was going to go here.
I got to my knees, with my hand still stroking Billy's cock and it was about an inch from my face. From this distance I could smell it. It didn't smell like my dick; it was a mix of sweat with his precum, which had a unique smell. I actually really enjoyed it, it turned me on a lot. I moved his dick around just to get a better look, I lifted it up to see the bottom of it, it was really thick and he had really esthetically nice big balls that were proportionate to his dick. I wanted to feel them so I lightly squeezed them with my other hand and they felt firm and full. Billy let out another moan when I grabbed his balls, again I felt good that I could easily take control of his pleasure right here and now. I looked at the top of his dick and he had a big vein that gave it a nice texture. I instinctively brought my face closer, just curious of his smell and having my face so close to his dick was quite thrilling. It just felt so taboo. I understood now why Jess was so turned on by it. I took in the smells and just got lost in a trance. It felt so naughty.
"Do you want to taste?" Billy asked. I didn't answer but I thought about it. I had my face already right beside his dick and for some reason my mouth was actually watering, it just looked so good. After a slight hesitation, I opened my mouth and took Billy's dick inside. His dick easily filled my mouth and I quickly tasted his precum and I enjoyed the taste. I saw Jess out of the corner of my eye who was sitting on the couch just staring at me going to work on Billy's dick, I could see she started to take her pants off. I lost track of what she was doing and focused on his dick, glad to notice that both Jessica and I were enjoying this. After a few seconds of blowing Billy, I started going on auto-pilot, part of me was mimicking all the porn that I had seen in my past and I just started mixing it up going between sucking, licking and kissing Billy's dick.
"Oh fuck! That feels amazing dude!" Billy let out as I licked him from the balls to the head of his beautiful dick. His positive reaction made me want to be even more naughty, I buried my face into his balls and starting licking his balls while stroking his dick. Again, I was infatuated by his smell and the naughtiness of the scene. "Oooh yeah man... you are really good at this!!"
I couldn't help to smile and laugh a little bit; I couldn't believe I was sucking a guy's dick and everyone was enjoying it in different ways. I didn't feel gay, I just felt extremely horny and turned on. I didn't feel like having to label myself, especially not in this moment, I was just going with it.
After a few minutes, Billy took his dick out of my mouth and I gasped for air.
"Holy shit man, that's really hot" Billy said. "Do you want to try something new?"
He gestured me to get on all fours on the living room rug. I obeyed but I was nervous. What was he exactly planning? Billy walked up behind me and started caressing my ass cheeks gently, it felt really good and calmed me. I looked back and saw that Jess was handing him lube and it was obvious what was going to happen next. Was I really going to get fucked in the ass tonight? I grew extremely horny but was really nervous about it. I looked over to Jessica, who was rubbing her clit through her panties, obviously enjoying the view. Jessica saw my concerned look and asked me: "You ok babe? Are you enjoying yourself?"
The fact that she was turned on by all of this and concerned about my well-being put me at ease. Maybe I should just give-in and enjoy the moment. I did really enjoy sucking on Billy's dick earlier, so maybe this will be good too. I also had some practice getting pegged by Jess a few times, and it always felt amazing so why would this be different?
"Yeah, this is really naughty, just a little nervous." I answered. "Are you enjoying it?"
"Oh my god, yes babe, this is the hottest thing I've ever seen. I'll tell you what, if you let Billy fuck your ass, I'll let you fuck my ass whenever you want" she said as she winked at me. That gave me another reason to let it happen.
Billy's dick was lubed up and ready to go. "I'll be gentle dude, don't worry, I know you're a first-timer, are you ready?"r"