No Young Guys, But It Happened

This is a work of fiction

It's crazy that you say you'll never do something, but end up doing it and enjoying it. Like how I said "I don't date or sleep with guys younger than me." Yet it happened and I'm not ashamed to admit it was not that bad. Let me tell you about my spicy night with a young man name Lamont.

It was a cold December night, me and a couple of my friends decided to hit our usual bar. We are a group that consists of cross dressers, drag queens, and trans people. Me I'm a 52 year old cross dressing man. I started cross dressing in my 20s, but finally embraced this life style a few years ago. Before I would dress up in private and occasionally drive around dressed.

I was married for 15 years to a woman, but things eventually ended. I never felt normal in the sense of being with a woman and yet I love women. Recently a year ago I had sex with a man and found out I really enjoyed it. So I guess I'm bisexual and not ashamed to admit it. He was around my age and was white like me. He was more leaner than me and taller to my smaller heavier stature.

I'm not obese, but I do have some weight. It does make my breast look nice and my ass rounded very nice. It's not the ghetto booty, but it was plump enough to fill out my outfits. I stand around 5'6 without heels, so I'm not very tall. When I dress up in my feminine clothes, I go by the persona Cassandra. As Cassandra I like to dress more modest and wear a nice blonde wig.

I really love wearing any hosiery products like stockings, tights, thigh high stockings, and old fashioned pantyhose. When I'm Cassandra, I'm confident and relaxed to the point I can go out in public dressed. I don't dress to hook up with guys or show off like a wild woman. I dress because I feel normal like this and it makes me happy. Still I do like some of the gentlemen's attention when I'm dressed.

I do occasionally have sex as Cassandra and I do enjoy being a bottom woman in the bedroom. The experience of feeling like a real woman as a guy kisses me or we're In the middle of sex. It's easy to sleep around, but I have a few rules for myself like not dating or sleeping with people I know in my normal life, or if they're married or in a relationship, last if they're younger than me.

I do get hit on by younger guys all the time and I do enjoy the attention, but they're like children. I'll go as far as several years younger, but that's it. The youngest guy I slept with was 39 years old. That soon changed when I met Lamont. We got to the bar and the usual crowd was in. Our group settled into our usual spot and began ordering drinks. A hour in, we were pretty comfortable and were slowly pouring out into the dance floor.

Eventually I made it to the dance floor and began dancing with my friends. I wore my typical style of dress, a figure hugging cocktail style dress with black sheer pantyhose and black stiletto heels. My blonde wig with a bow on the side. The hem of the dress was a few inches above my knees and would occasionally ride up to my thighs. As the night continues on, our group slowly started disappearing. Soon I decided to leave too.

I had to order an uber when my friend with the car left before I did. I walk down the street for a bit while I was on my phone trying to get a driver to accept my trip. I eventually canceled and continue walking for a while. I decided to stop at a convenient store to rest and grab a water. After buying a water and to try uber again, a random guy walks up to me and grabs my phone.

He sprints off and I couldn't run after him in heels. I couldn't believe my phone was stolen and I have to walk home in heels. I was angry and stormed off into the night when I hear someone yelling "hey you! Yeah you lady! Wait a second!" I turn to see a tall black man running up to me. "you want to rob me too!" I scolded at him. He was slightly out of breath and holding something in his hand. I looked down to see it was phone.

I quickly grabbed it and felt embarrassed to be rude to this guy. "I saw what happened and try to get your phone, but he tossed it the dumpster. I pulled it out and it was soaked." I hurriedly try to use my phone, but it wouldn't come on. It was still wet and needed to dry urgently. "thanks for getting it back. Sorry if I was rude." I apologized. He responded with "its ok, too bad your phone wet. You need to dry fast, but you look like you're far from home."

I nodded and said "a little far from home, yes. Thanks I'll just keep going" he quickly responded "my apartment is around the corner if you want to dry your phone. I'll let you use mine, but it's dead. Trust me it's better than walking in this freezing weather." It took a few minutes of us arguing before I accepted his offer. Along the way to his apartment he introduced himself as Phillip and he was out buying some stuff at the store when he saw me get robbed.

He also mentions he lives with his 19 year old son Lamont. We get to the apartment and he unlocks the door to some music. I go in and he quickly puts my phone in some rice to absorb the water. He invites me to sit and wait while my phone dries out. We talk for a bit until he realizes he has to go to work. I feel bad and offer to leave, but as a good Christian man he tells to stay and wait for my phone to dry.

So I sit at the kitchen table for a while after Phillip left. It was weird being in someone else's apartment. Then I hear someone enter the kitchen and see it was a tall good looking young black man. He had tattoos on his face and long braided hair. He wore no shirt that revealed his nicely tone body and tattoos. He was muscular with an athletic build. He had sweat pants on and he was not worried I was there.

"what's up. You waiting for your phone dry or some shit, right?" I nodded yes and said "I'll leave as soon as it dries." He act like he didn't hear me and started lighting up a blunt in the kitchen. I was shocked because I was there and he didn't care one bit. "why you all dressed up? You out partying or something?" I didn't want to respond to him while he was so rude, but I did. "yeah I was with some friends tonight. I don't dress like this all the time."

Again I couldn't tell if he was listening or even cared. He went in the living room and sat down on the couch. I sit there wondering about if he knew I was a cross dresser and if he would hurt me. I get up to use the bathroom and come back to see Lamont with my phone. "it needs to charge for a bit." I go over to see my phone was charging and it was dry. I unconsciously sit down to be next to my phone. "Hey here take a hit, you'll feel better."

I Try to reject his offer, but he wouldn't accept it. So I took a hit and realized I hadn't smoke weed in years. It hit me right away and I was feeling more relaxed now. I lean back on the couch and got comfortable. We took turns Taking hits off his blunt until it was gone. Afterwards we did have a little conversation and he does know I'm not a natural woman. He didn't seemed to care and continue our conversation.

I don't know if it was him or how this younger generation talks that makes feel annoyed, but the way he carrys himself and his demeanor made me feel different. He was young, but felt he was top dog and dominant this whole time. Slowly I'm starting to realize I was getting turned on and feeling attracted to him the longer I was around him. No I can't think like that, he's practically a child. A child who was legally an adult and was taller than you.

Those bad boy vibes were really strong and I feel my dick getting erected. "let me check my phone now." I blurted out awkwardly and stood up quick. I try to move away from him seeing my erection. Why is this happening? Why him? Crap am I wanting him to fuck me? So many questions raced in my head. When out of nowhere his hand covers my phone screen.

"I see you're all turned on and shit. You know you ain't bad looking with that dress and shit." I looked down to see he was now getting hard. Based on the out line of his cock, it was huge. He grabs my neck and leans in to kiss me. I try to resist, but our lips locked together anyway. He tosses my phone onto the floor and turns me back towards the couch. His tongue was dancing in my mouth and he was in control. I managed to break away from his lips.

"you're too young. It's not right. You're a baby." He smiles and caresses his cock outside his sweat pants and says "nah, this here is a man size dick. Your old ass bout to get some real dick." He grabs my neck again and my shoulder to push me on my back on the couch. My legs spread open and he lays on top of me. My legs wrap around his waist and he leans down to kiss my neck. It felt so good and I was slowly losing to temptation.

He starts slowly grinding his crotch into my lower stomach and I feel his enormous cock dig in me. My hands started massaging his back and my legs tighten their grip around his waist. "oh God, we can't. You're so young. It's not right. We should stop now." He continues dry humping and kissing my neck. I let deep breaths of excitement and passion. He started squeezing my thighs gently as he starts grinding harder.

He finally answers with "let me show you what a young nigga like me can do. This young nigga about to make you become his bitch." I usually don't like dirty talking, but this some reason had me begging for it to come true. "I think you're lacking experience honey." I whisper in his ear and he answered back "let me show you what I can do. After this you going to be my bitch. You'll be asking for this dick.. no begging for it!" I giggled and he went back to kissing my neck.

Now I started to kiss his neck and face. We continue this for a bit until I feel him stop kissing and sit up. He pulls his pants down to reveal his cock. It had his skin tone, long, thick, and veins everywhere. It was jaw dropping to tell the truth. It pulsate with eagerness and excitement. I don't know if I could fit it in me and will it hurt more than usual. I was losing my excitement and anxiety was taking over until he pulls my legs off him. He then directs them onto his shoulders and spits on his meaty cock.

He manhandled me like I was an object and I lay back, accepting my fate. He rips a hole in my pantyhose and spits in his hand to rub it on and in my ass. It made me shiver from his wet hands rubbing my asshole and slowly pushing his finger in me. He repeated this process a couple times until he figures he was ready. He uses hand to guide his cock towards my asshole. His cock head pushes against my asshole and rubs all over like he teasing. Finally he started to push harder and harder, finally able to make it through tight asshole.

Pain quickly shoots up my body and it was slowly getting worse. He managed to push a few inches of his thick cock in my ass, and that was all it took before he started to pumping in and out. He went slowly pumping his cock in me. He used my legs as handles as they lay on his shoulders. The pain was immense and a new feeling joined in on the action. I was getting light headed and that new feeling was winning over the pain. He slows down to start pushing in more of his cock in me.

I lay there taking more and more of his cock. I grip cushion of the couch harder as he continues to go further In me. Finally he succeeded in plunging his full erected cock in my ass. His balls were touching my ass cheeks. He went back to pumping in and out of me, but with his full cock. He squeezes my thighs hard and holds my legs against him as goes faster. He doesn't slow down and ramps up his speed. With each pump of his hips into mine, followed by a loud wet clapping noise.

His thrust were getting harder and was making my body bounce off his. Now I was feeling really good and was like I was floating out of my body. Loud deep sensual moans escape my mouth followed by heavy breathing. The couch was shaking under us, making dragging noises and small bangs. Who ever lived under them at the moment would definitely be awake. I never felt this before and I couldn't stay focused at all.

He starts slowly down and stops to drop my legs off his shoulders. He leans over me with his cock still in me. He continues pumping, but slowly this time. My legs wrap around his waist again and my hands land on his ass as he pumps away. I feel his tight ass and his lower stomach rubbing against my erected cock. The pain was almost completely gone and pure ecstasy takes over. My eyes on their own, began rolling backwards. He lays his body on top of me and easily covers my small body.

After a few minutes of being in missionary position, Lamont stops suddenly and says " let me hit that ass from the back." He pulls out and I obeyed his command by getting off my back, then get on my knees. I lean downwards and my ass high in the air for him to continue taking my ass. He grabs my hips and quickly reenters my ass with less resistance from my asshole. I didn't feel the pain like before and instead the pleasure returns.

He pounds away harder and faster than before. I was bouncing off his body with each mighty thrust. He was using my hips to pull me back as soon as I bounce forward. He was controlling the pace and me without thinking twice about it. "OH FUCK! FUCK! OH MY.... FUCK!" I said loudly between each of his thrust. This felt so good and I was giving into my instincts by moaning like a mad woman.

He smacks my ass every so often and say stuff like "TALE THIS DICK, BITCH!" or "LOVE THIS YOUNG DICK, HUH BITCH?" he eventually grabs my throat with one of his hands to pull my head backwards. My eyes were rolling backwards again and I started to cum. I cum all under me and the couch. Even after I cummed, I was still hard and pleasure was still in control.

Lamont was going strong, but soon he was slowing down and his thrust were getting less hard hitting. "Want this nut in your ass or your mouth?" he asks. At this point I was so out of it, I couldn't even speak. I felt like I was out of my body and was drunk. Only moans and grunts escape my mouth. He stops and let's out "I'M ABOUT TO BUST!" He pulls my body against his hard and holds it there while he does one hard final thrust.

I feel him fill my asshole with his cum. He leaves his cock in my ass for a minute before pulling out fully. After a few seconds, I feel his hot cum running down my ass and legs. I lay down completely wore out and exhausted. After a while we both get our composure and catch our breaths. My ass was so sore and raw from his huge cock. "told you this young dick can put in work."

I laugh and place my hand on his chest, feeling his muscular body and our combination of bodily fluids. "well I can admit I was wrong. To be honest, I thought you would cum in a few minutes. Now I see you can go the distance and beyond, Christ we went at it for almost 30 minutes." My hand slowly starts going downwards his body towards his flaccid cock to play with it.

I started massaging it and he closes his eyes in pleasure. To my surprise, his cock starts waking up and was quickly getting erected. I move close to him and got on my knees in front of him towering over me. I place his cock in my mouth and tasted our combined flavors. I sucked the head of his cock and I was slowly stroking his shaft. I go slow at first and made sure to get my spit all over his cock. I want it nice and wet to make it easier for both of us.

He starts slowly thrusting his hips towards my mouth to match my motions. I let go of his cock and hold his hips to let my mouth do the all the work. His cock would hit the back of my mouth throat easily and occasionally gag me. It took me a few minutes before I was able get his cock go down my throat. Luckily I learned to control my gag reflexes. He goes faster and holds my head as he fucks my face.

"Fuck this feels good, but I'm ready to fuck that ass again." I stop and stand up to slip off my dress. I left my pantyhose on and took off everything else. He grabs my shoulders and guides me to the kitchen counter. He turns me around and reaches down to grab my ass. He lifts me up and places me on the counter on my ass. He pulls my legs upwards and I lean back on my hands for support.

He leans forward and I wrap my hands around his neck to kiss him. We make out and our tongues wrestle between each other's mouths. We pulls away and spits on his cock. He quickly places my legs on his shoulders again and goes back to guiding his cock in my ass. He enters me again and uses his hands to grab my shoulders. He goes to thrusting away with my legs flaying around on his shoulders.

I hold onto his neck for support as he thrusts harder and faster. "OH FUCK! DON'T STOP! YOUR COCK FEELS SO GOOD! OH FUCK!" I moaned out loudly and in pleasure. He kisses me and I return the favor. My legs fall off his shoulders and I raise them to his sides. He starts grabbing my ass without breaking his stride and pulls me towards him. We were in the middle of it before his phone started ringing.

He stops and goes to answer his phone. "yeah. Nah, I'm in the middle of something. I'll hit you up tomorrow bruh." I slide off the counter and heads towards him. He sits on the couch with his legs spread apart. He spits in his hand and started rubbing all over his cock. "how about you ride this dick. Come here." I listen to his command and crawl onto him. I straddle him and guided his cock in my ass. He sucks on my nipples as I slowly let my ass swallow his cock.

I feel his cock go up in me and I start rolling my hips. I roll them back and forth fast while I hold his shoulders. He wraps his arms around my hips to hold me places I continue riding. "FUCK BABY! I LOVE YOUR BIG DICK! OH FUCK!" He squeezes my ass hard and starts thrusting upwards to match me. I gyrate my hips in a circular motion in one way and reverses the other way.

His thrust began to be stronger and harder, actually bouncing me up slightly. So I took the hint and bounce to match his movements. Loud wet clapping noises and the couch springs were filling the room along side of our moans. "you want to taste my nut?" he moans out to me. "YES! FUCK! CUM IN MY MOUTH BABY!" he stops thrusting and rolls me off him to lay on my back. He gets up quickly and with one hand starts stroking his cock. He steps next to me and with the other hand, he holds my head up and he crotches lower while still stroking his cock.

I open my mouth wide and stick my tongue out. The tip of the head of his cock was touching my tongue. I can taste the precum and it had a tangy taste to it. His loud grunts and moans were growing louder with the anticipation of him cumming. Then finally a large blast of cum lands on my tongue and cheeks. Then the second shot fully filled my mouth and lastly a few drops landed all over my face.

His cum tasted a little sweeter than the precum and I quickly place my mouth on the head of his cock. I swallow every drop I could and try to enjoy it too. I scoop the remaining on my face into my mouth and let that little bit marinate in my mouth. We rested for a bit and cleaned up. He was in the bathroom and all I'll could think about was did I really fuck a teenager? Well I mean he fucked me.

As much as I tried to find problems with what I did, I couldn't. Honestly he was the best lay I ever had. If he wanted to fuck again, I wouldn't say no at this point. I never cummed by getting fucked before. Actually I think I wanted him to try again. My small cock was hard again and I really want him to fuck me again. Damn I couldn't resist it anymore and I get up to walk to the bathroom. He just open the door and I fall on my knees in front of him.

I started sucking him again and it didn't take long before he was hard again. Unfortunately his phone rang and interrupted us. It was his dad and he was on the way home. So I got dressed and gave Lamont my number. "text me and we can finish this the right way. See you hun." I quickly got a uber and left to my home. He texted later and we set up a date to finish our fuck session.