He Wanted Sex In Lingerie

I have written before. I’m in my 40’s, I’m in good shape and I recently have tried having sex with men. If you’re considering it, and you’re straight and married to a woman as am I, you may get hooked. So, beware. 

Yes, I know, fucking men on the side is bad. I mean you risk STDs and you are cheating. It’s not honorable. Nevertheless, I tried it, I liked it and now sometimes I can’t seem to not do it. Particularly during a recent Halloween party.

It was a Saturday. My wife had us both at an adult Halloween gathering. It was a new group of friends and we knew very few people there. I decided to dress as Spider-Man. It was a tight sorta outfit. But I looked decent, I’m in decent shape. My wife was Wonder Woman. Yea…bad comic match I know. I was representing Marvel and she DC.

I was not even looking to hook up with a guy that night. I actually have not had any sex with men for months. Almost a year. Rather, my wife looked hot and, if anything, I was into her that night.

The mood of the party changed a bit later when people were drinking and my wife was off socializing. So, I did the same. I met a guy who clearly had a gay partner with him. The gay partner was somewhat flamboyant, seemed feminine and was friends with everyone…except my wife and I. To top that, they were dressed as Wilma and Fred. They had hilarious outfits. So, lisp, gay acting and dressed as Wilma? I figured Fred was gay.

Around midnight I talked to the guy dressed as Fred. His name was Kurt and was African American, dark skinned, muscular, hairy chested and clean shaved. I said, “Wow, your outfits are awesome!” He laughed, “Ah yea, and I’m 52, so you’re aging yourself if you know who I am.” I said, “I think even kids know The Flinstones? Right?” We continued with small talk. Kurt was dressed in basically a smock, a Flinstones smock. I was dressed in essentially spandex. As I turned to get a drink from the bar Kurt said “Nice ass, Spidey.”

I was not really thinking of Kurt that way but I was flattered. I had not been fucked by a wan in a long time. And there is something about the smell, the raw strength and the vulnerability that just feels awesome when a guy is fucking me. I’m a masculine male, but I like feeling like a guy is coming in me, like I’m a girl…I like a hard cock. I like the taste of cum. I grabbed my drink and the thoughts of this flooded my brain. I was now panicking. I was in spandex getting hard. Noooooo! I thought. I feverishly began thinking of how to solve quadratic equations so my hard cock didn’t show clearly through my spider suit.

It was no use. I order a rum and coke, turned around and hoped it was too dark for him to notice. I asked “Do you want anything?” Kurt smiled, “Do I? Mmmm…well if you’re talking drink, I’ll have what you’re having.” As I turned to the bar I again heard him flirt by saying “Any excuse to get you to turn around.” I don’t consider myself to have some amazing ass, but evidently Kurt liked it. My cock was now clearly sideways and visible to anyone who looked. I was hard as a rock. 

I continued small talk. I told him I’m a lawyer, he owned a medical business and he was engaged to Wilma…her name was actually Ben. So, my hard cock began to finally settle. Kurt brought up all kinds of small talk, we even discussed physics. Not sure how, but great conversation. My wife interrupted us saying we had to go. That was that. I was safe. I was not going to go there again with a guy.

I told Kurt, “Well, great taking to you. I will see you around.” Kurt said, here’s my card. Out of his tunic he pulled out a card. “My cell in on there. Call me sometime for lunch.” I took his card and said “Yea, that would be great.” I shook his hand and Kurt pulled me in for sort of a man hug. It was kinda awkward, but I figured it couldn’t hurt. He whispered, “I know you’re straight, but I would turn you into a woman Spider-Man.” With that strange comment we parted ways. I went home sexually frustrated. My wife was too intoxicated to fuck. Thus I went to bed horny.

First thing Monday, I called Kurt. I dreamed of what might happen, I fantasized and I was sexually frustrated all day Sunday. I almost even felt that my asshole was wet thinking of Kurt. That’s not possible, but damn, I was into him.

Kurt picked up and said, “Hello, Kurt here.” “Hi Kurt, this is Jack from the Halloween party Saturday.” Kurt paused, “Spider Man! I thought you’d never call.” I said, “Well, networking marketing, you know I like expanding my network. I am up for lunch.” Kurt and I talked a bit and he wouldn’t commit to lunch. We were into about 10 minutes of small talk and I was now figuring he was just flirting and really had no interest. That was fine. Then as he could tell I was about to move the conversation to a close, he said, “Will you text me, sext me? Hot pics? I’d like to see that ass with no spidey costume and your body?” I paused. Again, another very strange and forward request. I started, “Uh, well I…uh.” Kurt was polite, and said “Look, I kinda gotta go. But let’s sext. I’ll send you some hot pics.” I then reluctantly agreed and we hung up.

I was working remotely from home. So, I decided, against my better judgment, to text this guy naked pics. So, I trimmed my body hair, made sure my pubes were in order. I shaved my balls, shaved my ass so it looked clean. What an erotic feeling. I never took naked pics of myself except for maybe a dick pic. I was hard while shaving thinking of being fucked and I imagined his black cock in my mouth. I was so turned on.

I took three pictures. I got on all fours with my ass and back arched showing my curvy ass. I laid on my back with my cock hard. Then I took one with my underwear and my bulging hard cock filling them. I finished shooting for him within an hour. But I struggled with where these would end up. I couldn’t get my self to push the send. Then I did. I sent a man sexting pics. I could end up on the internet or on the news if I ever entered politics. What was I doing?

Kurt called immediately. “Hello, this is Jack.” Kurt was softly spoken, “Can I make you my girl today?” I was already hard. “Yes, I should not, but yes. Please.” Kurt rasped, “Wow, you are hot, you want it bad don’t you?” I said in a submissive way, “Yes.” Kurt then said, “I need you to shave all that hair on your chest, your arms, legs and stomach. I don’t like hair. Keep the hair around your dick, but trim it short. Be clean, very clean. I don’t like surprises. And I have an outfit for you.” I paused, this was a very long list. I asked, “When do you want to meet?” Kurt quickly said, “Now.” I agreed, we exchanged our goodbyes and I got to work looking shaved.

I never shaved my chest or arms. That was easy. I never shaved my legs. I have to say, as I did so my cock was fully erect and now I had precum. I was preparing for sex. I tasted my own precum as I prepared. It was sweet and salty. I had no time to run to the store, but knew exactly what meant by clean. I found an enema, emptied it, washed out and replaced it with warm water. I douched deep and twice. I had not done so in a while and as the nozzle pushed past the nerves on my sphincter, my entire body tingled. I was going to fuck this guy even if he wanted me to look like a girl doing it.

I was ready. I got to his house in a small gated community. He had a nice little place. I walked up to the door, and I was nervous. Very nervous. I had on a T-shirt, boxers and jeans. I didn’t know what this strange guy was actually into, and I just assumed I would also be into. He was very dominant though.

Kurt opened the door before I could know. He smile and said welcome. Kurt was dressed in tennis shorts and had no shirt on. His hair was less formal than the party and he immediately ushered me in. I heard the door close and he locked it behind me. I was almost shaking at this point. My hands were cold and I kept having thought that I shouldn’t be doing this.

 “Did you shave?” Kurt asked politely. I said back, “Yes, and it was quite an experience,”. “Oh yea,” Kurt replied, “How so?” I told him how I never shaved before. Further we discussed how I would explain to my wife my newly shaved body. As we talked, familiarity kicked in and I began feeling more comfortable. “Let’s see you naked Jack.” Kurt said, “Can I take off your clothes?” I sighed, “Yes.”

Kurt gently helped remove my shirt. As he did so he brushed his hand over my chest. “I like what I see.” My cock was now hard and exploding out of my jeans. Kurt gently unbuttoned and unzipped my pants. “Can I kiss you?” Kurt said softly. I didn’t respond, rather I pressed my lips against his as I felt his mouth open. I slipped my tongue across his tongue as I felt his hand slide into my boxer shorts holding my hard cock tightly. Kurt let go and backed away. I went in for more. He gently pushed me away. “Easy” he said as he removed my pants and underwear. “Mmm, you have a beautiful cock” Kurt said hungrily. He turned me around and went behind me. I felt his lips on my neck as his hand fully grabbed my ass cheeks. “Oh my, your ass is plump and deep.” Before I knew it, Kurt was on his knees. “Mmmm,” he moaned you smell amazing. I could feel him kissing and running his tongue up and down my ass crack.

I was moaning with pleasure and my mind was racing thinking of Kurt’s cock fucking me. Kurt then stood up and was clearly hard. I turned and saw his large cock through his tennis shorts. He was big and his cock had to be amazing. Kurt kissed me again on the lips, and pulled away. He walked over to the couch and said “Put this on.” It was lingerie. They appeared to be white. “Meet me in the bedroom, once you’re dressed.” He walked back into a dark hallway. I stood there naked and extremely horny.

I sat on the coach with the unfamiliar lingerie. They were white, clearly not new. Perhaps they were his lovers? I was not sure. I first looked at the underwear. They were sexy as it would pertain to girl standards. However, they had no back and a satin lacy pouch for the front. As I slid them on over my smooth shaved legs my cock fit in nicely and it held my balls tightly inside. He also had a top. It was white and backless. It was satin with white lace and clearly made for a flat chested female. I slid the tight top on. It was tight and showed my back, with a lady area over the nipples. Then there were stockings that seemed to come up to my thighs. I slid them on one at a time. I stood up and looked in the mirror. I was in lady lingerie. I actually looked and felt sexy. As I walked, my cock was tightly packaged in the panties and my man pussy was completely exposed. As I neared his room the excitement and nerves built. I could feel precum oozing onto my panties.

Kurt’s room was modern and stylish. He was a low white bed, cool lamps and a large bay windows overlooking a lake. He drew the curtains, which were also stylishly appointed. He walked from the bathroom, this time naked with a semi hard full cock. His tight black curls made his dick look bigger than what I imagined. I was 7 inches hard and he was at least that semi hard. That was going to be a lot to handle.

Kurt said nothing but approached me and immediately open mouth kissed me. I breathed heavy as I could feel his cock growing between us as our tongues clashed deeply in each others mouths. He was a sting and deep kisser. He deep strokes of his tongue were almost too much, he brushed his hard cock on my panties almost making me cum. I had to pull away. 

Kurt whispered, “Don’t pull away, I’m going fuck you so good baby.” My lips and tongue again clashed with his. I was so excited that as he continued to jump me my cock exploded in a small orgasm. He kissed me deeply as he reached into my panties grabbing my cock. He milked my cock wiping the abundance of cum onto his chest and stomach. “Your cum smells so good,” Kurt said hungrier now. “I wanna fuck. Can I fuck you baby?” I nodded. I came and was partially satisfied, but I was still semi hard and very horny. “Fuck me”, I said as I got on his low bed on my hands and knees. I arched my back like a good girl exposing my raw asshole.

Kurt said, “I’m on prep, can I fuck you bareback?” I was too invested to say no. I whispered, “I want you so badly, please fuck me bareback.” Before I could finish Kurt’s strong tongue was lashing deeply in my ass. He was rimming me better than I had ever felt. Each thrust of his tongue sent waves of pleasure through my body. Kurt reached around and pulled my messy cock out from my panties. He pulled it down and began sucking the tip. “Your cum taste so good,” he said as he sucked my now erect cock. As he let it go it sprang forward. Then Kurt slowly worked two of his large fingers into my ass. He licked my taint and balls, rimmed me and finally reached his fingers to my prostate. He began a rhythm, in and out. He was going to make me explode with an orgasm, but stopped.

Kurt came around the bed. “I want you to taste my precum.” I was now facing his hard black veiny cock. It was dark and amazing, he smelled like a man and I could faintly smell his cum. His cock dripped it and I took the head into my mouth. Kurt had a lot of girth and his cum was perfect. His precum was driving me wild. He was no more than 9 inches, but was very thick. He moaned as I massaged his balls and worked his thick cock into my mouth. I relaxed my throat and pushed the head back deeper and deeper. I could tell Kurt was enjoying this as his dick was tensing up and I could taste his salty sweet precum more and more. Now I was moaning as I knew he was going to give me his seed. The smell of Kurt was dirty, manly and musty. The taste of the cum. I wanted more. I would have swallowed every drop. Kurt suddenly pulled his cock from my mouth and was breathing heavy. “You are going to love the way I fuck you.” Kurt then had small streams of semen dripping from him. He was going to cum hard had I kept going.

Kurt went around me and again put his tongue in my hole. He intentionally left saliva this time. He was going to fuck me. My body was reeling. I wanted his thick full cock worse than I’ve ever wanted a cock before. I looked back and I saw him taking the cum I earlier left on his chest and he was wiping it on his hand, this his cock. “You’re going to love this.”

Kurt’s hard thick cock pushed against my asshole and it was big. It was hot and the cum and saliva made it very slick. Kurt whispered, “Relax, I’m going to make you feel good.” As I arched my back pushing against his hot stiff cock, I could feel his head slipping past my hole. But still there was girth, it didn’t go right in. I could feel Kurt adding more Alicia to my hole and he pushed the head through again. This time it was easier and went a bit deeper. He pulled out, and the next time he gently pushed again, even easier and every pleasure nerve in my body was activated. I could feel waves of pleasure from my asshole up through my body. I reached back and pulled his ass into me. His full cock then slid into my canal deeply. I heard him moan loudly, “You are so tight, you’re gonna make me cum.” I pushed my ass back and began grinding his cock. “Oh no, you’re going to make me cum.” Kurt pulled out.

He then turned me over. His cock was stiff and shaking it was so hard. My cock exited my panties and was dripping with precum. I was ready for more. I complied with his non-verbal request and spread my legs lifted them up. Kurt gently grabbed my knees and exposed my man pussy. Kurt took his hard cock and slid it into me deeply, stretching me but filling me with him. Our lips met and our tongues lashed in and out as he thrust in and out of me. It was the most incredible sex, as he thrust his dick deeper into me his tongue was deeper in my mouth. I could smell the dirty sex, the saliva, the cum, I could hear his heavy balls slapping into my ass and I could hear the cum and saliva between his raw cock and my ass. I moaned loudly as I could feel him hitting my prostrate. He hit it again, and again and again. I couldn’t take it anymore. I began cumming wildly all over my stomach, with each thrust of Kurt’s cock pushing the semen out. He pulled out of me, lubricated his dick with my cum and pushed his 9 inches deeply back into me. “I want you to show me how a girl fucks me. Ride me!” He turned on his back with his aching hard member jutting out looking for sex. He guided me to ride him.

Like a woman, I crawled onto him and grabbed his hot black cock. “You want me to fuck you?” I moaned in a sexy manner. Kurt grabbed my hips, and said “Yes, baby fuck me hard, fuck me like you want it, take my cum.” As he aggressively pulled my hips over his manhood, I grabbed his cock and directed into me.

I sat up and thrust my hips forward jutting out my stomach like a woman. My panties were covered in cum but were there. Panties. My bra. It was all too surreal. My pussy was being fucked deeply and I was riding him like a girl. I felt so sexy. I rubbed my nipples through the satin sheen top. My nipples were hard a sensitive. I pushed my ass out and tried to grab his cock as I pulled up and them slammed down filling me up. I wanted him to cum in me so bad. I was being penetrated deeper than ever before. “Fuck me.” he kept panting, “Right there, fuck me!” As I slammed his cock into me up and down I could feel him tightening up. He was going to cum. “Fuck, fuck, fuck, keep going. Fuck.” Kurt grabbed my shoulders and pulled me down to him, as he kissed me heavily while moaning. Kurt began the thrusting hard. I was on top, but he was kissing me and thrusting his hard cock deeply and hard in me. Smack, smack, smack and then he exploded. His hot cum poured deeply in me.

Kurt thrust his hot member deeply into me and released my lips as he moaned in ecstasy. Stream after stream pumped into me. I could feel the warm hot cum flowing out of me onto his public hair. His delicious hot pubic hair.

I fell off of him. We were both spent. I had an incredible prostate orgasm and Kurt came more than I could imagine. After our sex, Kurt got up and rushed me out. “My fiancé will be home.” He said. I cleaned up in the bathroom, took off the lingerie and got in my clothes. Kurt ushered me towards the door. I handed him the lingerie and he said “No, keep them. You’ll need them maybe again sometime?” I smiled and winked. “Sure.” Off I went.

Here I am today. I did it again. You might ask, what did I tell my wife about the shaving? I told her I just wanted to see if she thought it was sexy. Ironically, she did not. She thought it was weird. And so, another great great sexual experience. I have vowed again to not keep doing this in 2023.