A Night to Remember

I was certain that J was the only man I ever wanted to be with and eager to give him a night he’d never forget.

As soon as I got home that afternoon I began trying on everything I had. I wanted to pick something J would really enjoy and I wanted to give him a night he wouldn’t soon forget.

After trying on every piece of women’s clothing I had for in and out of the bedroom, I still couldn’t come up with anything. J had been calling me daily for the past 2 weeks hoping we could get together. We had been on a break for nearly 4 months while I tried to figure out who I was and after feeling confident I found the answers I was looking for, I wanted to see him as bad as he wanted to see me.

I called J that evening and he was very excited to talk and even more excited when I asked him if we could see each other that weekend. J and I attended separate high schools but only about 20 miles apart. Neither of us had any interest in waiting another 3 days until the weekend.

After being on the phone together for just a few minutes, J said he was coming over to my house and there was nothing I could do about it. As much as I fantasized about that weekend being special, I wasn’t about to stop him from coming over. I should’ve expected this but being so heavily focused on that weekend, it completely slipped my mind that we both had cars, and lived 20 minutes apart and he could be here in a half hour’s time.

Sure enough J showed up about 45 minutes later. As soon as I opened the door J leaned in and kissed me. Not considering that my mom could be nearby at all. Fortunately she was already in bed and no one saw it.

The was no small talk of any kind. Instead, we headed to my bedroom and closed the door. I always put a chair in front of the door just in case my mom tried to get in while we were doing stuff. When I finished moving the chair, I turned around and J was already sitting on the edge of the bed with pants around his ankles and his beautiful black cock sticking straight up. I missed him and that dick so much over 4 months!

I wasted no time in getting on my knees and going to work on him. I missed the way his cock smelled and tasted. I missed how rock hard it got but was still so soft to the touch. His balls had a salty taste to them that I just loved! J came in my mouth in less than a minute!

We laid in bed together for about an hour and just talked about our time apart and we mutually agreed that we were back together. I sucked his cock once more. This time he lasted 5 minutes or so before cumming in my mouth. Afterwards he went home. After all it was still a school night.

We made plans to hangout that Friday and Saturday night. It was decided that I would spend the weekend at his house which was always my preference.

J worked at a pizza place on Friday nights so we couldn’t get together until after midnight. My plan was to show up early and get ready to surprise him.

I spent all evening getting as much ready as I could at home so I wouldn’t have too much to do when I got there. I shaved my entire body minus a small patch of pubes. I had bought a set of fake nails and painted them dark red. I had never wore fake nails before. I packed everything I needed into a backpack and headed over to J’s.

J’s dad answered the door and was pleased to see me. His boyfriend Mark was as well despite what we had done just a few days before. The two of them were both handymen. They loved interior design and remodeling things and just before J and I took our break, they started a project to turn their basement into another living quarters. Their plan was to rent it out after J headed to college but for the time being, J had moved his stuff down there. They were both extremely excited and eager to show me their handiwork and I pretended to be amused but all I could think about was J.

Once finished showing off their hard work, Mark said the two of them were going to bed. J’s dad told me to make myself comfortable as I was always welcome. Then they headed upstairs.

They really had done a great job at making their standard run of the mill basement into a nice living area. There was a couch and TV area. A bathroom but no shower yet. A small kitchen area and a bedroom. I had no idea J had his own living area now. His old bedroom was down the hall from his dad’s and now instead of it being upstairs, it was in the basement which offered a lot more privacy.

I checked my watch and it was just after 11pm. J wasn’t getting home for about an hour. I decided I was going to take a quick shower before he arrived so for that I did have to go upstairs. So, wearing only a towel, I quietly headed upstairs and took a very quick shower.

As I carefully exited the bathroom, now completely naked, I peeked to see if the coast was clear and it was. As I tiptoed past the bedroom of J’s dad and Mark, I heard them having sex. I was a little pressed for time but I figured I could enjoy this for a minute or so. Even though I had visual of what was going on in there, I had my imagination and their noises. I listened while gently stroking my dick in the dark hallway for a few minutes until I heard what I assumed was one of them having an orgasm.

Walking through someone else’s house completely naked, now with a hard on, is a little awkward but once I got to the basement, my erection subsided a bit and I began to get dressed. I had taken an outfit from my mom that i knew J thought was sexy but I was very scared my mom would notice it missing.

The first piece of clothing I put on was the underwear. It consisted on black lace panties, a matching black lace bra and a garter belt which I had black silk stockings. I had my mom’s favorite red dress. It was sleeveless, V cut that exposed what cleavage my chubby body had. I had found some black high heels that were a half size too small but I was able to squeeze my feet into them. I had been growing my hair long for almost two years now and it was halfway down my back. While I had gotten the hang of the makeup, I still struggled doing my hair sometimes. This time I brushed it and clipped it up. I put on all my mascara, eyeliner, blush and lipstick. It was the best I had ever looked and I was so proud of myself. A quick spray of perfume that J had bought for me and I was ready, with no time to spare either.

Just as I put the perfume bottle down I heard J open the door to the basement and start heading downstairs. I sat on his couch sipping on these awful wine coolers that his dad kept in the refrigerator downstairs. As J walked around the corner and saw me he had a huge smile on his face.

“Wow, you look beautiful!” He said as he kissed me and hugged me.

“Thank you, baby.” I replied in as sexy tone as I could.

J quickly headed upstairs to shower the pizza scent from his body. As he showered, I sat and sipped on Bartles and James wine coolers. I was just finishing my 4 bottle as J crept back downstairs. I was feeling a bit buzzed by now!

J stood 5 feet away completely naked. His abs were glistening from his shower and his cock was semi erect just kind of bobbing up and down as it slowly filled with his blood. He approached me and wrapped his arms around my waist and we began kissing. The scent of pizza was gone and replaced by cleanliness and shea butter. He smelled amazing and looked even better.

J sat on the couch while I went to the refrigerator and grabbed two more drinks. I handed one to him and started drinking the other. After a few sips, I got down on my knees between his legs and began slowly stroking his now rock hard cock. Our eyes were locked on each other as I began to tease the tip of his dick with my tongue. I’ve missed his thick 8” black cock so much!

I slowly work my way from teasing him to fully engulfing as much of his dick in my mouth as I can. J lets out a sigh of relief. I can feel his body loosening as he sinks into the couch. I can’t have him cum yet though..

Next I get up and sit on his lap, grinding my ass on his throbbing cock. I slowly begin to remove my dress. Straddling him, I sensually pull on strap from my shoulder. Followed by the other. As I pull the red dress down exposing my black lace bra, J’s strong hands reach up and grab my breasts. He pulls the bra down just enough for my tits to come out. He goes in for a taste. First he bites my nipple the he swirls his tongue around it. My nipples are as hard as his cock now. I hold his head in place like a mother breastfeeding her child. I don’t want it to stop! I love my nipples sucked on! But I’m loving it too much and I can feel that I’m getting closer to cumming!

I release his head and shove my tongue in his mouth. His hands make their way to my ass cheeks and he gives me a tiny little spank before he squeezes. I dig my nails into his upper back!

Now I stand and drop my dress to the floor. J runs his hands up my stockings until he gets to my panties. He pulls them down and I kick them off. His warm mouth now wrapped around my cock as he continues to squeeze my ass. I run my fake nails through what little hair he has sending goosebumps down his back.

J lays down on the couch and signals for me to join him. I get on top of him and we are in our favorite position. 69ing. We enjoy each others cocks for a few minutes before we get up and head to the bedroom.

J closes the bedroom door behind him and holds me in his arms as we kiss some more. He lays me down on the center of his king size bed. I had already placed a bottle of lubricant on the bed waiting for us. J climbs between my legs in a missionary position. Squirts a healthy amount of lube on his cock and presses it against my eager hole. Once again our eyes are locked on each other as his manhood slides inside of me almost effortlessly. I bite my lip and gasp a bit but it feels incredible!

J begins to grind and thrust into me. I wrap my legs around his waist and match his movements. My nails once again dig into his back and I start to pant.

“I’m so close, baby!” I moan

He thrusts a bit harder and a bit faster. His mouth right next to my ear. His breathing increases.

“I’m there. I’m gonna cum!” He whispers in my ear

“Me too!” I cry out.

I feel his cock begin to pulse inside of my ass. At the same time I release three days of cum I had been saving for this night. I could feel both of us cumming and neither of us wanted it to stop.

J gently pulls his cock from my ass and lays next to me. I turn to my side so he can spoon me. We’re both out of breath. I have cum trickling from my cock and his from my ass.

No more than 2 minutes go by and J smacks ass softly and pushes his cock back into my ass.

“Oh my god?” I cry out a bit shocked “..you’re already for more?” I ask obviously knowing the answer

“We just made love, now I’m gonna fuck you!” J replied as he began the thrust himself in and out of me.

“Oh god!” I cry out “…yes! I wanna be fucked by that cock!”

J pulls out and gets on his knees. He pulls me into my hands and knees and plunges his thick black manhood back into my stretched out hole. His strong hands grab my thick hips. His thrusting is so aggressive that I feel his massive balls slapping against mine. I bury my face in his pillow as he pounds away at my fat ass.

J fucked me doggystyle for about 20 minutes before he finally exploded once again inside me. Once again I feel his cock pulsing as it releases spurt after spurt of hot cum inside me. In that moment I fantasize about him putting a baby inside me. So much so that I yell it out.

“Yes! Yes! Put a baby in me, J!” I moan

J lets out some very primal grunts and summons the energy for a few more hard thrusts. Cum is draining down my legs. The smell of sweat and sex now permeate through the room. J finally removes his cock from my ass and collapses on the bed. I do the same. We’re both exhausted in very different ways. That was without question the longest he had ever lasted inside me! I’m out of gas and unbelievably satisfied!

Before I can even fully regain my ability to breathe, J is already asleep next to me. I pull the sheets over our sweaty bodies and cuddle up next to him. I fall asleep minutes later.

J and I are still friends. We are both married and as a matter of fact our wives have been friends for many years as well. J and his wife set me up with my wife. A few years ago we told them about everything we had done. As you can guess it came as quite the shock to them both. The official story is that we haven’t done anything with each other since college. At least that’s what we told the wives. The truth is.. I still have an incredible wardrobe of women’s clothes and we still have a secret relationship. We have a few bars that we go to once in a while and we find time to fool around. Whether it’s a blowjob in the car or driving out to the middle of no where and fucking in a field somewhere.

And once every couple months we tell our wives we’re going fishing for the weekend. We have never once gone fishing. We get a nice hotel room and we spend the weekend together. I actually have a good story about one of those weekends… next time.

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