I was in a major sex drought and my confidence was dwindling but a younger man showed me I have a lot more to give before I’m done.
As an overweight bisexual cross dressing weirdo in your mid 40’s, things don’t always go your way. The older I get, the less confidence I have I myself, and not just sexually but my life in general.
I’ve been going through a drought sexually lately. My wife is not interested as much, and the times I’ve gone out looking for a man to have some fun with, I’ve struck out. In my twenties I was able to deal with droughts, especially since I had my friend J. Him and I have had a secret sexual relationship since we were teenagers. However, time with him gets few and far between the older we get. In fact J and I haven’t been together for over 6 months.
I decided to make an attempt at crawling out of my head and go out to a club. I needed to get out of the house anyways so why not try and have some fun at the same time.
I spent a good hour in the shower shaving my entire body. For some reason when I shave my balls I get rock hard and have to masturbate right there in the shower. Once I finished that up, I got out of the shower and did my hair and makeup. I’ve never been good at the makeup side of cross dressing but I’m getting better slowly.
I picked out a pair of white cotton panties and a bra. I’m overweight enough that I can wear a B cup bra. I decided to go more casual and picked out a cute shirt and put on a pair of jeans. Very tight jeans I might add. I’m not much of a bragger but these jeans make my big ass look pretty fucking great!
The club I went to was one I had never been to before. It was way on the other side of the city. As soon as I walked in I noticed I was NOT the only crossdressing weirdo there. That lowered my confidence a bit more as I now had some competition.
I was just about to finish my second drink when a younger man came and sat next to me. His name was Ben. We sparked up a conversation quickly and had a couple drinks together.
He told me he was only 22 and that it was his first time in a gay and lesbian club. As we continued to talk he also revealed that he had never been with a man before, only women.
We had another drink and then he finally got the nerve to ask me if I wanted to go home with him. I agreed and we got up and headed out. We walked to the parking lot where coincidentally he had parked his truck right next to my car. We talked in the parking lot for a few minutes, and I could tell that he was incredibly nervous.
“You seem very nervous, Ben.” I said wondering if there was more to it than just nerves
“I’m just new at this and not sure how it works, that’s all. Sorry.” He said
“Don’t be sorry, and don’t be nervous. I promise if we go back to your place, you’re gonna get laid.” I said with a smirk
Ben laughed a bit and it looked like he calmed just a bit. I decided to close the small gap between us and put my arms around his waist. I leaned in and kissed him. Then I kissed him a second time and then I felt his hands around my waist and he squeezed my ass. We kissed in the parking lot for a minute or so and then I agreed to follow him back to his place.
After a short drive I arrived at Ben’s apartment building. Once again I we parked next to each other and spent a minute or so kissing in that parking lot as well.
“Let’s go inside before someone sees us.” He said nervously
Some might be mildly insulted by that but I understood why he was nervous and scared so I just agreed and we went u to his little studio apartment.
The only furniture Ben had was a bed and a gaming chair so I sat on the edge of his bed as he grabbed us a couple more beers from his refrigerator. He handed one to me and we both took a big drink and placed it on the desk.
“Now, let’s see what you got for me.” I said as I grabbed him by the waistband and pulled him in front of me.
I unbuttoned the front of his jeans and pulled his pants and underwear down. Ben’s dick was between 5-6”, nothing special but it was rock hard!
I wrapped my cold hand around the base of his shaft and put his throbbing cock in my mouth. The first thing I noticed was his cock smelled and tasted amazing! I appreciated his cleanliness!
Ben let out a loud sigh and began running his fingers through my hair as my head bobbed back and forth on his dick.
“God, that feels good!” He moaned
Ben stood me up and lifted my shirt over my head. I quickly unbuttoned my jeans and shimmied out of them. Ben had removed all of his clothing in excitement and I finished removing mine as well!
The first thing Ben did once our clothes were spread all over the floor was grab my tits. He leaned in and began sucking on one of my nipples while pinching the other. Let me be crystal clear here: I FUCKING LOVE MY NIPPLES PLAYED WITH AND SUCKED ON! I can’t get enough of it! I have had orgasms just from my tits being sucked on!
Ben was really enjoying himself with my tits and I had no intention of stopping him. He had his cock in one hand, mine in his other hand and my nipples pinched between his teeth with his tongue flicking it. I thought I was going to shoot cum all over the room at that moment.
“I want to fuck you so badly!” He groaned before aggressively kissing me
“I want you to fuck me!” I responded “..how do you want me, baby?”
“From behind!” He muttered as he began shuffling through his desk for something
I got on his bed on all fours. I had my big ass pointed directly at him and I wiggled it for him. He continued to shuffle through his drawer but stare at my ass in anticipation. Then he finally found what he was looking for. He pulled out a tube of lubricant.
“Wait, do I need a condom?” He asked
“I’m clean but if you want to that’s fine with me.” I answered
Ben slammed his drawer shut and jumped on the bed. He didn’t have a condom which I was glad. He quickly squirted some lube on his dick, smacked my ass and positioned himself behind me. I felt to cold lube touch my ass hole and then his cock begin to push. Seconds later he had thrust his entire cock inside me. It hurt for a few seconds, but I didn’t let him know that. I just buried my face in his pillow and began to moan as Ben thrusted his manhood in and out of my eager hole. His hands had a firm grip on my hips and he wasn’t wasting anytime savoring the moment. Right from the beginning he was fucking me as hard as he could. If his cock was bigger I would’ve turned around and smacked the shit out of him but he was just the right size for this.
Ben had been fucking me for no more than a minute when I felt him squeeze my hips and bend over my back. He let out a loud groan. He had cum inside me!
As quickly as he had came, he pulled out and collapsed on the bed out of breath. I laid down next to him equally out of breath.
“Sorry that was so short.” He said gasping for air
“It’s ok. As long as you enjoyed yourself.” I answered
Normally I would’ve wanted to go a lot longer and do a lot more than 50 seconds of fucking but Ben was sweet and it was his first time so I didn’t want to make him feel bad. Plus I hoped when he caught his breath, we’d go for round two. Unfortunately, that didn’t happen.
We laid and talked for about a half hour before I realized round two wasn’t coming and I got up and got dressed. I left after we exchanged numbers. We agreed to meet up again.
Ben texted me a few times after that and we agreed to meet up again next week. I wasn’t super excited about it but I wasn’t going to say no.
Then Ben made it interesting. He threw me a curveball like no one ever has. I went from mildly interested in him to full scale holy shit!
We began talking and sexting back and forth about things we liked and things we wanted to do to each other. Most of it was just him being overzealous. I liked his enthusiasm. And as someone in their mid 40’s, seeing his youthfulness excited me.
One particular thing he mentioned turned me on so much that I almost drove the 45 minutes to his apartment right then and there!
Ben wants to roleplay.. with me being his mom! What?! Since I was just a kid I have been unbelievably attracted to my mom and always wanted to fuck her. I never did such a thing with her but the fact that he wanted to do that, coupled with my kink, that sent me off.
“I would love to be your mommy.” I answered
