It had been so long since I had some dick.
I haven’t posted anything here in a while but tonight was a good night and I thought it was worth sharing.
I’ve been so incredibly lonely the last year or so, my relationship with the girl I was with for the past 6 years didn’t survive the pandemic. Apparently when you quarantine two people in the same apartment, they quickly grow to hate each other. As frustrated as I was, I didn’t want the relationship to end, but it wasn’t my choice.
In the year since the split, I have dated a couple girls and nothing came of it. Neither lasted beyond the second date. I hooked up with another girl at the bar and had a one night stand but that was the only sex I have had since the breakup.
My ex-girlfriend was very open to my bisexuality in the beginning of the relationship but about a year or so into it, she began to change.
We would regularly cross dress together. She loved fucking my ass with her collection of strap ons. She enjoyed being the man sometimes and I loved being a woman.
When I first started having sex with men I was always the top. I had a friend, Jayson, that would let me fuck him. He was my first boyfriend. Later on as I got into my 20’s I started craving being a bottom. It eventually lead towards cross dressing. When I got into it, I went all in. I had an entire wardrobe, not just underwear and lingerie but shoes, jeans, shirts, dresses.. like, an entire wardrobe for any occasion. 99% of the time I would sleep in women’s underwear and nightgowns and such. I love the feel of the lace and silk on my body.
Since the break up I had completely ignored that side of me. I believe she did her best to push that side of me away and make me forget about it the best she could.
About a week ago I was digging thru my closet and found a bag with a bunch of my lingerie and panties and such. Just the feel of the silk in my hands turned me on a bit and I decided to put the silk nightgown on. I pulled a pair of cotton panties out of the bag and put them on. I immediately went to my bedroom and masturbated. I ended up sleeping in them that night and it awoke everything inside me that I buried over the past few years.
Over the past week I’ve more or less lived as the girl version of me: Stephanie. The only time I wasn’t in women’s clothes was when I went to work. Yesterday I went to work and wore panties, a bra, and even nylons under my suit. I sat in my office staring at my computer all day dreaming of going home and masturbating. I wanted to shove a dildo up my ass so bad!
At 5 o’clock I raced home. As I entered my apartment I ripped off my suit, and jumped in my bed. I started stroking my cock. I reached over and grabbed my 6” dildo and suction cupped it to the wall. I picked the 6” one because I hadn’t done this in a long time so I had to start smaller.
I got on all fours and pressed my tight eager hole against the tip of the dildo. As I backed against it, the tip slipped inside my ass.
“Oh shit!” I moaned out
It felt so damn good! I slowly pushed back a little more and slid it in a bit deeper. I began to rock back and forth and as the dildo slid in and out of my hole, I began to lose all focus on what I was doing. Before I knew it a hot wad of cum squirted all over my bed. I had never cum hands free before. It was quite good!
I finished up and took a shower. When I was done I put on a pair of soft cotton panties, and some cute pajama pants, and a girly tank top. I even pulled out a blonde wig, put it in a ponytail to complete the look. For so long I had natural long hair and didn’t need my wigs anymore. Popped some popcorn and spent the entire night watching old episodes of the OC. When I was ready for bed, I masturbated once again and slept like a baby for the first time in ages.
When I woke up this morning I was happy. Happy for the first time in a long time. I enjoyed fucking myself last night!
As my stay-at-home Saturday went on, I did all my chores dressed in my women’s clothing. I lived the whole day as Stephanie. By evening I was so horny!
I laid in bed, my sweatpants and panties wrapped around my ankles and my tank top pulled up exposing my tiny tits. As one hand pinched and played with my nipples, my other hand stroked my cock pretending I was playing with my pussy. By the time I was done I had made the decision to go out. I wanted some real dick!
I showered once again, and looked for something to wear. I started with a red lace bra and a matching thong. I pulled out a set of red silk stockings and a garter belt to match. I found a tight white mini dress and some heels. I put on my blonde wig and did my makeup and stepped out of the house as Stephanie for the first time in over 3 years.
I went to the bar that I used to frequent. Technically it’s a gay bar, but I’ve met plenty of straight people there as well.
After about an hour sitting at the end of the bar, the bartender hands me another martini and points to the other end of the bar to an older man. He appeared to be in his late 40’s, he had salt and pepper hair, light stubble beard, a fairly good physique and was wearing a gray suit, similar to the one I wear to work.
I smiled at him and took a sip of the martini. He smiled back, stood up and walked over.
“You have a beautiful smile.” He said as he sat next to me.
“Thanks.” I replied turning toward him and flashing my smile once again.
“I”m Paul.” He said
“Stephanie.” I said back melting at how I felt so good to tell him I was Stephanie tonight!
We talked and had a couple more drinks together. He was funny and intelligent. He had a similar job to what I do for a living but I pretended I knew nothing about it so I could make him think I thought he was interesting, when in truth he wasn’t.
I’m 27 now and I hadn’t been with another guy since I was 24. Paul was actually 51. We casually discussed the age difference and I pretended that it was a little weird when in reality I didn’t care.
“So listen.” I said stopping the conversation dead in its tracks. “I’m gonna make this real easy for you. I haven’t been fucked in a long time. You’re not my type for a relationship but I’m gonna let you fuck me tonight, ok?” I explained.
“Wow! That sounds good to me.” He said as he finished off his drink and stood up and took my hand.
We walked the six blocks back to my apartment. He held my hand the entire way back which was kind of sweet. We talked a bit more and he seemed like a sweetheart. He was divorced and lonely as well. Has 3 kids. The truth was, he was too old for a relationship, plus I don’t even know that I want a relationship with a guy right now, but he was sweet and I wanted to be fucked by him!
As we got to my apartment door, I turned towards him and kissed him as softly as I could. As I pulled away, he grabbed me and kissed me much more passionately. His stubble tickled my face, and his tongue swirled with mine. His cologne smelled like an old guy which was a bit of a turn off. I prefer a man’s natural smell as opposed to cologne. His hands grabbed a hold of my ass cheeks. He had strong hands! His mouth moved to my neck and he began sucking and kissing my neck and ears. I fumbled thru my purse looking for my keys to the apartment. His hands hiked my dress up in back and he squeezed my bare ass. Then he pressed himself against me squishing me between him and the door. I could feel his hard cock pressing against my lower stomach. I finally pushed him away as I found my keys and opened the door. As it shut, he resumed groping and nibbling on me. My cock so unbelievably hard as well.
I couldn’t wait any longer, I got down on my knees right there in the entryway and began undoing his belt and pants. I aggressively yanked his pants and underwear down to his knees. His cock popped straight up and the tip hit my nose. He was HUGE! His cock was at least 9” and thick! I had been fucked by cocks this big before, including my own 8”. A long time ago my ex and I bought one of those kits to make your own dildo and we made a clone of my cock. She would use it to fuck me all the time. Oddly enough, she took it when she left me.. hmm..
I was a bit nervous seeing his cock because it’s been so long since I had been with a man, and even longer since I was with a man this big but I knew I was in too deep, no pun intended, and had to go the distance.
I was so turned on that any nerves I had vanished as quickly as they came as I grabbed hold of the base of his shaft, opened my mouth and stuck his cock in my mouth. My head bobbed back and forth and his cock slid in and out of my mouth. Gliding across my tongue and hitting the back of my throat.
I continued to suck his cock for a few minutes before he grabbed my arm and stood me up. He grabbed my dress and yanked it up over my head. He bent down and ran his tongue from my belly button up to my bra. Goosebumps covered my body. As his tongue reached my bra, his hands slid underneath it and pushed it up. He started to lick and gently nibble on my nipples as he reached around and unhooked my bra and throwing it across the room. My cock had fallen out of my thong which was so skimpy that it’s amazing I’m able to keep it in there when I’m soft. His hand reached down and started to rub the tip of my cock.
“Holy shit, you got a big dick!” He said returning to my neck and earlobe
“You do too! I want it in me!” I said trying to catch my breath
I grabbed his hand and led him to the bedroom. I didn’t want anymore fore play, I just wanted to get fucked! I reached in my drawer and grabbed some lube and a condom and handed it to him. I held out my hand and he squirted some lube in my hand and I rubbed it on my ass. I got on all fours and felt him get behind me. I took a deep breath as his tip hit my hole and pushed. It’s different when there’s a real man behind you instead of a dildo stuck to the wall. You don’t get to decide how hard you’re fucked.
Before I could let out the breath in my lungs his tip popped inside my hole.
“Oh fuck!” I cried out.
His right hand on the base of his shaft hold it in place and his left hand now on my hip, holding me in place. As he pushed his cock deeper, he pulled me closer. His cock was almost all the way in now!!
Then he pulled his hips back and his cock slid out a little, then thrust it a little deeper. He did it again and went even deeper this time. Each thrust he went a little deeper.
“Wow!” He grunted
“Oh my god, are you all the way in?!” I asked giggling and moaning at the same time
“Mmmhmm!” He grunted again
His thrusts we’re getting harder and harder now. I felt his balls swinging forward and slapping against my balls and legs.
Paul leaned forward and put his hand on the back of my head and shoved it down into the pillow. I couldn’t breathe as I screamed into the pillow. He was fully pounding my asshole now! It hurt a bit and I couldn’t breathe too well but this was more than I hoped for. I wanted to be thoroughly fucked, and that’s exactly what was happening! He pulled his cock out of my ass!
“Roll over, I’m gonna cum!” He yelled
I didn’t hesitate! I rolled over and sat up in time to see him rip the condom off. Paul had his hand squeezing the base of his shaft. I grabbed a hold of his cock as Paul released his grip. Before I could fully open my mouth, a hot load of cum shot on my face hitting me just above the eye and a huge glob on my nose. As I opened my mouth and stuck out my tongue, another hot shot of cum spurted in and landed on the back of my tongue and slid down my throat. The glob from my nose dropped down onto the tip of my tongue and down my chin. Another spurt hit my chin and a final spurt hit my chest. As the last few drops slowly trickled out, I put Paul’s cock in my mouth and sucked the last of his hot cum out. I swallowed as much as I could, wiping what was left on my face and putting it in my mouth.
“Wow! I needed that!” He moaned out letting out a sigh of relief.
“Christ, so did I!” I said wiping up a few drops of cum on my chest and licking it off my finger.
Paul collapsed on my bed and laid down. I laid next to him out of breath. My asshole hurt a bit but I loved it! I needed that!
A minute or so passed and Paul finally broke the exhausted silence..
“You gonna fuck me now?” He asked
“Do you want me to?” I asked
“If you want to, you can. I can take it.” Paul explained
I rolled over and reached in my drawer and grabbed another condom. Paul rolled over and I spooned him. I put the condom on, covered it in lube and softly pressed my cock against his butthole. Once inside I fucked him for about a minute before I felt like cumming. One final thrust and I exploded inside his middle age ass!
“That was unexpected.” I said rolling on to my back with the condom, full of cum still tightly wrapped around my cock.
“Well, seems a little unfair for me to get all the pleasure.” Paul said rolling over to face me.
“Trust me, you may not think so, but tonight I got more pleasure being fucked by you, than fucking you. When I say I needed that, I meant it.” I confessed “..wanna get cleaned up?” I asked
Paul and I went and took a shower together as I liked doing after sex. We made out in the hot shower for a few minutes, soaped each other up, and I ran my fingers thru his manly chest hair which I hadn’t noticed he had since he didn’t take his shirt off during sex. I love a man with manly chest hair!!!
Paul and I dried off and went to bed. We slept naked together and he held me until we fell asleep. This morning when we woke up, I sucked his cock before he left.
Just before I started writing this we spoke on the phone. I wasn’t expecting this but we decided that we would continue to see each other. It’s going to be casual as he’s only seeing Stephanie. The guy side of me still wants a girl…
We’re going on a date tomorrow night, if it goes well, I’ll kiss and tell haha!
👄This will be the best oral sex you have ever experienced.👅