My First Time Alone with Jimmy

It had been a little over 6 months since the last time Jimmy was in town. Lynn and I talked about our last encounter quite a bit and even had time to play with another bi guy we met locally. The bi play was limited to just oral and I was craving more after the last encounter we had with Jimmy.

It was a long day and we were just getting around to dinner when I got a text. It was from Jimmy and said he was in town for the night wanted to know if we could play. I showed Lynn the text already knowing there was no way she could get motivated to play and she just wanted to go to bed. She confirmed with a disappointed look and said she wished she could but she was exhausted and wanted to go to bed.

To my surprise, she then suggested that I take the opportunity and play with him myself. Had I been in the middle of a bite or a drink I probably would have choked. I looked at her and stuttered some intelligible words. Even though she replied right away with a smile and a nod, it seemed like an eternity.

This was a new twist in our swinging relationship. I wasn't even sure I wanted to play with Jimmy without her. My mind was thinking no but I could not help but feeling aroused at the same time. Then I thought to myself, Jimmy isn't going to want to play with just me. I don't have to make a decision because he's going to say no anyway. So I told her thank you and I'll text Jimmy but I'm sure he's not interested. She chuckled a bit and saying I shouldn't be too sure about that.

So I sent a text to Jimmy that Lynn was out of commission for the night but that I have a hall pass for the night. I added that I was sure that did not interest him but that Lynn threw it out there. A couple of minutes passed with no response and I started thinking that I may have ruined what we all had by even mentioning it.

I was about to say something to Lynn when my phone vibrated. I froze for a second not sure if I wanted to look but then picked up my phone hoping he wasn't offended. The reply froze me again. He asked if by a hall pass, did I mean it to meet someone else or if I meant to play with him.

No matter how many times I read the text, I could not tell if it implied interest or not so I sent a simple reply telling him that he and I can play. This time the reply was lightning fast and one word, sure. I told Lynn he said yes but I did not know how to respond and was feeling a bit odd about it. She said text him back and let him know you're a bit nervous and see what he says.

We settled on him showing up at our place around 830 and we'll take it from there. Lynn crashed in the guest bedroom right after dinner leaving me to my thoughts. I felt so nervous for the next 2 hours I smoked 2 full joints just trying to relax a bit.

Jimmy showed up around 8:35. During the 5 minutes between 8:30 and 8:35 I was sure he wasn't going to show until I saw the headlights in the driveway. I opened the door and stuck out my hand to shake with him. It felt awkward and informal shaking his hand thinking in a few minutes we were going to be having sex.

After shutting the door I mentioned Lynn was already asleep in the guest room and we'd be going upstairs to our bedroom. When we got to the room I pulled out a joint and asked if he wanted to smoke. He said he did earlier and was all set but would if I wanted to. I joked about smoking twice already to calm my nerves. He stepped up to me and placed his hand on my crotch and rubbed my growing cock in my jeans.

Jimmy leaned in against me and got right to my ear and said just relax and then brushed along my neck as he slowly went to his knees rubbing against my body the whole way. He slowly undid my belt and zipper as I stepped out of my shoes. He pulled my jeans and underwear down so I could step out of those as well.

Jimmy slowly runs his hands up the back of my legs as he lifts his head to my cock. Moving my now erect cock to one side he gently licks and sucks on my sack as he squeezes my cock in his hand. My head is tilted back and my eyes closed imagining what it would look like if I could step out of the situation and be watching.

As I lose myself in thought I am quickly brought back to reality when Jimmy takes my cock in his mouth and begins to suck on me slowly. The fact that it is just him and I playing and no one else is there is even more of a turn on. My hands find his head and I hold it as he works on my cock with his mouth. Jimmy reaches up with one hand and pinches one of my nipples as he goes deep on my cock. It was an amazing feeling and caused me to push his head deeper on my cock before backing off.

As he lowered his hand he pushed on the inside of my thigh to signal me to lift my leg and rest it on the bed. Jimmy then reached between my legs and started rubbing my ass. He licked his finger and found my asshole and began rubbing it gently as he sucked me. Slowly he worked his finger in my ass just a little bit and then picked up the pace of his sucking on my cock. He then pushed his finger in a little deeper and went all the way down on my cock. I gasped and my knees suddenly got weak as I erupted into his mouth almost losing my balance from the leg I'm standing on turning to rubber.

Jimmy helps me lower my leg from the bed and stands up again pressing against me but this time he lifts my shirt over my head as he stands up and stops at my nipple to suck and nibble on it. As he comes up he says I swallowed most of it but I'm sure you can still taste it as he presses his mouth against mine and starts to kiss me.

I had never kissed a guy before but I was so turned on I really didn't think about it and kissed him back. It was definitely different than kissing a woman. It was less gentle and, well, different.

Feeling his clothes against my skin I realized I was completely naked but he was fully dressed. I reached my hand down to his crotch and began rubbing his cock through his jeans. He was hard as a rock.

I pulled back from our kiss and went to my knees. Unbuckling his belt and jeans I slid his pants down then pulling down his underwear his cock sprung out almost hitting me in the face. I wrapped my hand around his growing cock and directed it to my mouth. Running my tongue over the head of his cock I could taste his pre-cum oozing from his cock. I gently stroke his cock as I take the head in my mouth still twirling my tongue around the tip. Releasing my hand from his cock, I take him deeper into my mouth. I was amazed at how hard he was.

Jimmy has an awesome cock. A little over 8 inches and circumcised. Still being new at sucking cock I still can't take him fully in my mouth as my gag reflexes kick in. I continued sucking on his cock and fondling his balls. Reaching behind him I grab his ass with both hands and pull him towards me to force his cock in my throat. I almost take it all before gagging. Pulling his cock from his mouth I gather myself a bit as Jimmy suggests we get on the bed.

I laid back on the bed as Jimmy removed the rest of his clothes. Jimmy climbed up on top of me grinding his cock against mine as our naked bodies pressed against each other. Once again he started kissing me and this time it was much more erotic with our bodies rubbing and hands on each other. My cock was nearly fully erect again. I'm only about 7.5 inches and definitely not as thick as Jimmy but it was hot to feel my cock rubbing against his.

He pulls back from the kiss and slides up so he's almost straddling my chest and rests his cock right on my lips. I begin sucking on him again and he slowly starts to move his hips as if to fuck my mouth. I run my hands along his hips and up his sides. I reach up and pinch both of his nipples causing him to thrust his cock deeper in my mouth. After a few more deep sucks, Jimmy slides off my chest onto the bed next to me to catch his breath.

Turning to his side he looks at me and says, "why don't you turn over so I can fuck that nice ass of yours". I reach over to the nightstand and grab the lube and hand it to him. I look at the condom I had prepared and set next to the lube but I didn't hand that to him with the lube. I will be very glad I did not.

I get into a doggie position on the bed and Jimmy settles in behind me. He presses up against me so his cock is between my legs and rubbing against my balls and the bottom of my cock. He continues with this slow thrusting getting me even more aroused with the cock to cock contact. He then dribbles some lube into the crack of my ass allowing it to run down to my asshole. He re-positions his cock between the cheeks of my ass and rubs his cock along the crack of my ass allowing the lube to coat his cock.

Jimmy asks if I want him to use a condom and I think I mumbled no because the next thing I felt was the head of his cock against my asshole. Grabbing my hips he gently pulls me towards him until I feel the pop of the head of his cock entering my ass. Pressing slowly, Jimmy inches his cock deeper into my ass until I can feel his body against my ass and know he is in all the way. I gently rock back to make sure I'm getting every inch of his cock in my ass.

Jimmy fucked me once before during a threesome with Lynn. While I did enjoy him fucking me, It was fairly quick and a bit rough. This time he was a lot slower and it was very much about us both enjoying it. Jimmy rubbed his hands on my back and up my sides as he slowly fucked me pausing each time he was all the way deep I my ass. Last time he didn't say much as he fucked me. This time he was talking as he fucked me.

Asking if I liked how his cock felt and telling me how tight my ass was and how good it felt. I responded with talk of my own telling him how much I liked it and asked him to fuck me harder. Jimmy picked up the pace and got to the point he was slamming against my ass as he fucked me.

I could tell he was enjoying it and getting closer to cumming by his talk until finally he said "I'm going to cum inside you" as he grabbed my hips and thrust into my ass deeper than ever and I felt his cock twitch inside me.

Suddenly I felt him cumming in my ass. It felt warm and I could feel his cock continue to pump his cum in my ass. He pulled back a bit and then started to fuck me some more. After having him buried deep in my ass and filling me with cum I could barely feel him fucking me but he continued for a few minutes until I noticed him going soft. When the head of his cock pulled from my ass I felt the cum drip from my ass. I collapsed forward laying on my stomach catching my breath.

Jimmy laid on the bed and I rolled over a bit exposing my now fully erect cock. Reaching down and taking it in his hand he mentioned how last time I didn't get to fuck him and that he would really like to feel my cock in his ass. Till now I had not topped a guy and Lynn and I had anal sex maybe twice. It was never up high on my agenda but I figured why not.

Jimmy bends over the end of the bed and I step up behind him. I put some lube on my cock and then a little on my finger and rub it around his asshole. Jimmy pushes back a bit so my finger penetrates his ass and he lets out a deep sigh. Removing my finger, I line the head of my cock up with his ass and press the head of my cock into his ass.

Not being as thick as Jimmy, the head of my cock easily entered his ass. As soon as he felt me in, Jimmy pushed back hard to take my whole cock at once. I quickly grabbed his hips to avoid having to step back. I pulled my cock out to the the head and then quickly thrust my cock back in his ass as hard and fast as I could triggering a moan from Jimmy. Grabbing Jimmy's hips I began to pull back to the point of almost being out and then slamming my cock back in his ass. With each thrust I picked up the pace.

Before I knew it I was fucking Jimmy like a jackhammer. Having already cum I was not feeling like I was going to be able to cum again and sustain the pace I was fucking him. I slowed my pace down slightly and kept making long and slow thrusts. After a minute or two I felt that familiar tingle in my balls that said I was getting ready to cum. I made one quick push of my cock in his ass and held it deep. I felt Jimmy tense his ass a bit and squeeze my cock and that was all it took. I felt my second load of the night erupting from my cock now buried inside his ass.

As we both collapse on the bed Jimmy says "how about that joint now?"