I had sex with a man for the first time in a long time and I wanted more!
My phone rang early this morning and woke me up. Immediately I was annoyed since I was on vacation from work this week but when I looked at the number, I noticed it was Paul.
Paul was an older man, in his early 50’s I had hooked up with a few nights ago. When I met him at the bar, I was fully intended to be a one night thing. I’m in my late 20’s, a man of his age is not what I’m looking. The night was so incredible though and he treated me exactly how I wanted to be treated that I decided to see where this went. Plus, for a 51 year old man, he was gorgeous!
“Hello?” I answered
“Yeah, is Stephanie there?” He asked
I love that he asked for Stephanie! It turned me on to be honest!
I pretended to go get Stephanie and proceeded to get into my cross dressing other side of me.
“Hey sweetie!” I said in the most feminine way I could.
Paul asked me if I wanted to get some dinner tonight, and as nervous as I was about going out in public, I agreed to join him. It’s one thing getting dressed up and going to a gay bar but going to a nice restaurant or a movie theater is a totally different thing.
I started getting ready by showering and shaving every hair on my body that wasn’t on the top of my head. We were just going to a steakhouse, nothing fancy so I decided to just dress for the situation.
I started by putting on a fake chest piece that I had. When I first started cross dressing, I had gotten a fake tits chest piece that wears sort of like a shirt, but the tits were stupid big. It looked ridiculous. I still have it but rarely do I wear it. This newer one is a B cup which looks much more realistic to my frame.
Next I picked out a bra and panty combo. Despite dressing somewhat casual tonight, I wanted something sexy underneath. I picked a black silk pair of panties and a black bra to match. I had gotten these from Victoria’s Secret website but don’t remember ever wearing them. The bra fit perfectly on my fake B cup tits!
I grabbed the tightest jeans I have and squeezed into them. Then I put on a cute little top that I have. I did my makeup as best I could, I admit I’m still not good at it and probably never will be no matter how many instructional videos I watch on YouTube. Put on a blonde wig, gave myself a quick look in the mirror and wasn’t completely pleased with my appearance but Paul was going to be here in 10 minutes and I didn’t have time to do anything different.
When I heard the knock on my apartment door, a lump formed in my throat and I got butterflies in my stomach. I opened the door and saw Paul standing there with a smile. He was also wearing jeans and a sports coat. He had shaved his facial stubble clean except for a mustache which for some fucked up reason I found sexy as fuck! I wanted to pull him inside and suck his cock right then and there!
I contained my libido as I locked my door and we headed to Paul’s car. He held my hand as we walked and he opened the car door for me. Salt and pepper hair, chest hair, a mustache and he opens doors for girls? Totally old fashioned and it made me so fucking wet!
We had a fairly uneventful dinner. We talked about stuff, but truthfully the age difference does make it hard to have much in common. Once I was out in public and focused on Paul, I completely forgot about if people were staring at me or if they even noticed I was a man in drag or anything. I just enjoyed myself. Paul made me very relaxed. After dinner we stopped and got some ice cream. Then went back to my apartment.
As we approached my apartment door, once again his hands got grabby. Maybe some girls would’ve been offended by this but I wanted him so bad that I was annoyed it took him this long.
We made out for a few minutes in the apartment hall. A few people came thru and saw us and I didn’t care, much like the restaurant, I was so focused on Paul.
We opened the apartment door and sat on my couch. I offered him a beer and he accepted. As he took his first sip, I climbed between his legs and began undoing his belt and pants.
“You’re not gonna let me finish my beer?” Paul asked
“You’re a man, and you work hard for a living. Let me treat you like a man.” I said as seductively as I could
Paul say back a bit as I pulled his jeans and tighty whiteys down to his ankles. He took another sip of his beer, as I grabbed his shaft and put the tip in my mouth. I began to run my fingernails up and down his thigh. I could feel his goosebumps forming.
Paul set his beer on the table next to my couch and started unbuttoning his shirt. As he opened his shirt revealing his dark chest hair. My tongue began to swirl around the tip of his cock as I looked up and made eye contact with him. I started running my hand up his stomach to his chest to run my fingers thru his chest hair. Paul’s head fell back and he stared at the ceiling. Seconds later I felt his cock start to swell and then a blast of hot cum hit the roof of my mouth and slid down my throat. A second and equally strong blast did the same as the first. A third and fourth followed and as I tried to keep up by swallowing it, cum began dripping down my chin.
Paul looked down at me as I spit his cock out. I wiped the cum from my chin and put it in my mouth. Paul took my hand and pulled me on his lap. I straddled him and he kissed me intensely.
“No one has ever made me cum that quickly before.” Paul said. “I’m kind of embarrassed.” He added
“Don’t be. I’m flattered.” I said back with a smile and returned to kissing him, then I climbed off his lap and Paul finished his beer.
“I didn’t ruin the night or your plans?” He asked
“It’s only 9:30, the nights not over. We got all night!” I answered. “I’m gonna go put something more comfortable on, why don’t you pick out a movie for us to watch.” I added as I headed for my bedroom.
When I got to my room I dug thru my “other” dresser that I keep all my girl clothes in and found some Pink shorts to wear. I shimmied my way out of those tight jeans and slid the shorts up my legs admiring how soft and smooth I had made them for a second. I took my shirt and bra off. Then I removed the fake breasts piece I had on and just put on a comfortable tank top. I took the time to place the lube and a couple condoms on the side table drawer next to my bed so I was prepared. I walked out to the front room and Paul was sitting on the couch in his underwear and nothing else. It was quite hot today and I didn’t have my AC on while we were gone so it was a bit warm in my apartment. I didn’t care because his sweat was making his chest hair gleam.
I say next to Paul and cuddled up next to him, running my fingers thru his sweaty chest hair again and kissing him as I draped my smooth leg over his hairy leg. His hand slid up my thigh and squeezed my ass cheek.
“You took the tits off?” He asked
“Yeah. That damn thing is made of rubber and makes me sweat like a pig. Is that ok?” I explained
“Of course.” He responded
We started watching a movie but it didn’t last long. A half hour into the movie Paul’s hand began to move up and down my thigh. I could see his cock getting harder and harder inside those tighty whiteys he had on and I knew we weren’t going to finish this movie anytime soon.
Once again my fingers returned to his chest hair and I began kissing his shoulder and neck. Paul turned towards me and we started making out passionately. His mustache tickled my nose but I loved it. Stephanie has some serious daddy issues to be so attracted to this type of man.
“Don’t you wanna finish the movie first?” Paul whispered
“I’ve never been this horny in my life! If we sit here another hour watching this movie, I’m going to explode!” I explained as I stood up and took Paul’s hand.
I didn’t even bother to turn off the tv as I lead Paul to my bedroom. Paul closed the door behind him and walked towards the bed where I sat on the corner. I yanked down his underwear and his cock stood straight up. 9 inches of pure manhood stared me right in the face again and I opened my mouth and put it inside once again. I proceeded to suck his cock for a few minutes until I just couldn’t take it anymore!
“Lay down!” I demanded
Paul did as I said and laid down on my bed. I took off all my clothes, grabbed a condom and put it on his big dick. Squirted a bunch of lube on it and set the tube aside. I straddled Paul and reached down and grabbed his shaft and placed the tip against my eager hole. I sat down slowly as his cock slid all the way inside me. I cried out in pain as his entire manhood went inside me. It hurt like hell for a few seconds until I realized how badly I wanted his cock! I ignored the pain knowing it would subside any second and began to ride Paul’s dong. My hard cock slapped against his stomach with each grind I did. I leaned forward and placed both my hands on Paul’s pecs feeling his chest muscles and grabbing a hold of his chest hair. Then I squirted cum all over his stomach and chest. It was the single most intense orgasm I’ve ever had!
“Holy shit that was amazing!” Paul’s said
“You have no idea!” I said out of breath
“My turn!” Paul exclaimed “..get on your hands and knees!”
I did exactly as he demanded. I loved that he was such a manly man that knew exactly what he wanted and took control!
I got on all fours and Paul positioned himself behind me. Just as I did when I sat down on his cock, he plunged his entire manhood balls deep inside me. My asshole was much more eager now and offered much less resistance. Still though, there was a second or two of uncomfortable pain. Then, Paul grabbed ahold of my hips and began fucking me. Deep, and hard! I moaned and cried so loud that my neighbors definitely heard me.
“Oh god! Fuck that ass!” I screamed out.
When Paul fucked me a few nights ago, he didn’t last very long, but that blowjob I gave him 45 minutes ago must’ve really helped. Paul pounded my ass for almost 10 minutes! We changed positions a few times. As badly as I wanted his cock inside me, I wanted to send him home a happy man.
We were in a missionary position now as Paul pulled his cock out of my stretched out ass, ripped the condom from his sweaty cock and sprayed another hot load all over my stomach. I swiped some of it up with my finger and put it in my mouth. His cum tasted amazing. I could tell he ate a healthy diet. I’ve sucked dicks of unhealthy guys and their cum doesn’t taste as good. Paul’s cum was white gold! No matter where I go or what I do, I don’t think I could ever get sick of his cock and cum.
We were a hot sweaty, cum covered mess so we got up and immediately jumped in the shower together, just as we did a few nights ago. Again, we soaped each other’s bodies and made out a little bit.
“Will you spend the night with me?” I asked as we dried off
“I’ll have to leave early so I can go home and get some clothes for work but yeah, I’ll stay.” He answered
Paul went to my bedroom first and climbed into bed naked. I put on some scented girly lotion for him and joined him. We laid awake talking for a little while and it was really hard not to jump his bones again. Lying there naked with him just made me think about cock and cum constantly!
His phone alarm went off at 5:30am. I was already awake as I couldn’t sleep. As the alarm went off, Paul reached across my body and shut off his phone. I felt his hard morning wood cock against my leg. I knew he was hard because as I couldn’t sleep, I took the blankets off and stared at his dick, even gently playing with it making it harder as he slept.
“I gotta get up, babe.” He said in a groggy voice
Loving that he called me “babe” made me all warm and fuzzy feeling on top of my perpetual hornyness around him.
“Let me take care of this before you go.” I said as I grabbed a handful of his cock.
“You’re gonna make me late to work.” He said in his least resistant voice.
“Not if you cum as quickly as you did last night.” I said back with a chuckle as I put his cock in my mouth again.
Once inside my mouth, there was no resistance from him. Once again I sucked his cock and longed for his cum. Shortly after I heard him moaning a bit and sure enough a warm load of cum hit the back of my throat. I sucked every last drop from his balls, swallowing every drop.
“Keep treating me like this and I’m gonna have to marry you” Paul said as he got up and began to get dressed.
He then went to the bathroom for a minute or so. I was a little put off by that marriage comment but I took it with a grain of salt. I’m sure he didn’t mean it.
“You busy tonight?” Paul asked as he re entered the room fully dressed now. “..I thought I’d come over after work tonight.. if that’s ok with you.”
“Of course!” I said laying there naked with the taste of cum still on my lips.
I saw Paul to the door, kissed him for a minute or so and told him how excited I was to see him after work. I immediately went back to bed as I knew how exhausting it was getting my ass pounded last night and if tonight is like last night, I’m going to need my rest.
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