Gay Male cross dressing stories
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A football player of some sort, Tony had a look about him that said, "My mom let me dress myself today." He would have been an easy target to pick on if he didn't stand well over six feet tall and have arms the size of my thighs. I just want you to take off your clothes and put on this outfit," he said with a wry grin, indicating a blouse and skirt that were laid out on the couch next to him. The taste of his cum still fresh in my mouth, Tony went over to the TV to pop out the VHS tape of my escapades and said, "In case the photos weren't enough motivation."
Tom tensed up, his legs shot straight out, his cock increased in girth, his balls contracted and then he released his man juice with great fury directly into Tim’s waiting mouth. When Tom finally stopped coming, Tim took Tom’s cock and used it to scoop the remaining cum from his face back to his mouth. He placed Tim’s stocking covered legs over his shoulders, placed his fat cockhead to his opening and in one quick motion drove his entire cock all the way in Tim’s willing man pussy. Tom fucked Tim for a long time before he was able to drench Tim’s rectum with another load of hot thick man seed.
He said, "Cindy, I am going to treat you right, and take good care of your steaming hot wet pussy, so that when I'm done with you you'll be a true cock slut sissy gurl." To say he hit the spot would be an understatement and my only reply was my address and an invitation to come over that same night whenever he wanted. "You feel like a sissy slut don't you, in panties and lipstick...you want daddy to keep fucking you until he cums inside you don't you?" he asked. "Aw yeah," he shouted, "take that big dick, baby, take daddy's big fat cock up that sweet pussy cunt!" We became animalistic in our fucking and I kept looking back over my shoulder into his eyes.
As I grabbed his cock he slipped his right hand between my cheeks and started working a finger into my already lubed hole. Realizing that Sam did not cum I slowly eased off his cock and turned to kiss my way down. After another passionate kiss that slowly turned gentle I said, “Make love to me Sam. I want nothing more than to feel you cum inside me while we are making love.” Laying there intertwined with Sam still inside of me, I started feeling very emotional as we continued to kiss. After kissing him hard and pushing him back into me with my heels on his ass cheeks I breathlessly replied, “You better get that cock hard again because I am going to wear it out.”
What I do in an hour at the office, takes the morons at work two days to complete. On my way home, on the first day the wall was being built, I observed two bricklayers eating during their lunch break. Leisurely he began pushing his dick to and fro, as my mouth and throat adjusted to his entry. Pulling his knob out he told me to take a deep breath, before reinserting his cock all the way. I hoped like hell that he would be back the following day, and began praying that the wall would take forever to complete. Duane did visit the following day, and for the further week that the wall took to finish.
In the past, I had asked my girlfriends to let me suck their dildos after they had used them, and secretly always had wondered what a cock would taste like, but being confronted with the real thing was a whole different story. Maybe it was being locked up in chastity for so long and enjoying the vicarious pleasure I was giving Damien, or maybe it was the fact that I genuinely liked sucking cock and just never admitted it to myself. "Just take a deep breath," Damien said, slowly pushing the head of his cock into my ass. I couldn't deny loving the fact a huge black guy's cum was inside me, filling me, and making me his little sissy bitch.
I never would have be able to think of another boy as "beautiful" or attractive at all before the time spent on my knees serving as Tony's bitch. But now I was drinking in Billy, my mouth watering with desire, my whole world focused on him as he came close enough to wrap his arms around me, my mouth opening to his tongue, his tender lips crushed against mine. After that, I felt the tightness of his opening as I pushed deeper, wondering how far I could go, hearing him gasp a little but immediately nod after, signalling me to continue. I knew that that evening as I serviced Tony's cock, I would be thinking of Billy and wishing it was him.
We got to my apartment, we sat down on the couch and I asked him if he was married to which he said yes, that his wife and 3 kids were in Mexico and he’s been sending them money more and kept on sucking him, I got on the couch and he started to grab my ass and my waist, he spanked my ass a couple of times and kept sucking his dick, that he squeezed my ass hard and then grabbed his cock and started to slap my going to cum, I stopped got up told him to fuck me in the ass. a big grind on my face, my cock was now semi-hard and went with cum, he looked let me feel how big and strong his cock was compared to mine, mine felt like a
I know you look as guys cocks all the time and wish you were sucking them. Open your mouth and take in his cock and suck it clean.” After I finished cleaning his beautiful cock Gene told me to kneel in front of him and masturbate. After you cum I want you to lick it up and swallow it all.” I did as I was instructed and loved every minute. He then turned his attention back to Mary and gave her a very long fucking and once again shot his cum deep inside her. The entire time I was giving pleasure to Stan I had Sid’s cock in my right hand as I slowly jerked him.
He rubbed my tight virgin ass for a few minutes before I felt him start to penetrate a little, It was amazing. It’s a good thing nobody was around when I came out, coming out of the mens room looking like a teenage girl. He stopped spanking me, and got up off the bed, unzipping his pants and letting them fall. He pulled off, “Ohh, bitch doesnt like sucking cock?” He pulled my thong down around my knees and started probing with his dick, just rubbing against my tight ass. “Good thing you’re messy when you suck, my cock’s already lubed up.” He stopped probing my ass for a second, and walked away.
I know when a guy is hitting on me so I smiled back and said, “Bill I’m glad you like skinny because I am skinny all over.” As I opened my mouth he pushed forward and his cock slide right in to the back of my throat. So lost I didn’t at first see the closet door open and his wife emerge with a cam recorder in her hand. Bill’s cock slid right in until his heavy balls were resting on my ass. He kissed me and the said, “I have dreamed of this moment for five years ever since I saw you for the first time in school.
I drove there and was waiting in my car when a young man jogged up in shorts and t-shirt. “Are you meeting Dean?” Stephen asked. Dean had a tube of lube in his hand and was covering Stephen’s cock and rubbing it between his butt cheeks. Stephen held Dean’s hips and started to thrust. I leaned into it so that each movement he and Stephen made thrust Dean’s cock into my mouth. Stephen’s hands held onto Dean’s hips to steady him each time he thrust his big cock upward. With Dean’s cock still in my mouth I felt each twitch and squirt of Stephen’s orgasm. With both men finally exhausted and Dean’s cock shrinking out of my mouth, we all uncoupled and lay back on the mattress.
I thought of Philip and how he had been so surprised and turned on by me wearing my wife’s underwear, how he had kissed me sensually and how good his mouth had felt around my penis. Momentum was building quickly and the only thought I had in my head was of Philip pounding my ass while his twin was taking my hard cock down his throat. As I looked at the girly clothes I started to get aroused all over again but I knew that if I wanted to fit into my panties I couldn’t afford another erection although I did permit myself a feel from my anus to the base of my cock.
Tony held his hand out for them, I handed them over and he brought them to his face as I for the first time in my life took a pair of silky pink panties and stepped into them, I pulled them up, when they hit my dick and balls I almost shot a load, nothing had felt so nice and I liked looking pretty for Tony. I was shocked and surprised at how his finger seemed to belong there, like my ass had been waiting for it all of this time, he worked his finger around my hole as we kissed and I played with his dick and balls. Tony broke lose from our kiss "I need to fuck you, I need a girl" he told me.
“I’m actually waiting for a friend,” Jamie finally said, still refusing to make eye contact with the man as he looked back at the dance floor, hoping he would spot Rachel now. “Shhh…” Seemed to be the only response from Rachel as he pulled the boy along and finally pushed him into the very last stall of the row, quickly locking the door behind them and looking back at Jamie with a dirty grin spread across his cheeks; a grin that only meant one thing. Jamie could only stare in awe as Rachel took it deeper and deeper, who finally let out a sigh as he felt his round large ass hit the cold cubicle wall leaving it there for a few seconds.
Lionel blushed a little and tried to shift himself around, "I like a guy wearing tights (Pantyhose) maybe fancy panties or, stockings and suspenders, it really gets me hot fr fucking him, you interested?" He came back with a small case and opened it to reveal, tights of different colours, panties and french knickers, stockings with matching suspender belt, I thought they looked rather nice to be honest. I told him what had happened, he got the pill bottle and NONE of the tablets left said paracetamol on them there were only three,,, Lionel looked at me and started to cry "I had Mike here the night you split up, he must have changed the tablets, let me see what yiu have" I dropped my jogging bottoms, sat on the bed and opened my legs.....
I knocked on the room 126, and I heard him say "Its open baby, come in", and once while we were talking he said he never had a blowjob and I promised that would be the first thing I did for him. I walked over to him, and told him that I've waited months for this, and he grabbed me by my jacket and started to kiss me, and Then I kicked my shoes off and climbed on top of him, and we made out for 10 minutes. I stood their naked and he said to me "Give me my first fuck ever, and it better be good Baby", I laughed and said "I promise it will be".
As I toyed with his silky fat tube Antonio placed his hands on my cheeks and ran his thumbs over my lips, before pushing them into my mouth. After pushing my shorts down slightly Antonio said, “This hair also has to be shaved Stanley, and the hair on your legs.” Moving towards me and placing his right hand on my neck, Antonio pushed his fingers upwards into my hair. A short while later, Antonio asked me to place my arms around his neck before he lifted my body, and cradled in his arms carried me to the bedroom. Mercifully, a month later I received a call from Antonio asking me if I would employ a younger cousin of his named Juan, a twenty-one-year old whom he highly recommended.
Mike’s cock shot hot milky onto my hand and nylon covered thighs. I slowly sat on his knee and now Mike released my cock and began to wank me. The feeling of someone else’s hand on my cock was electric and it took only a few strokes before my orgasm shot spunk onto Mike’s thighs. Our cocks were hard once again and as Mike lay back on the bed I kissed down his hard body. I slowly took each toe in my mouth kissing and sucking whilst my hands stoked those hard thighs. When I came out and went to the bedroom I heard Mike in the en suite and found a pink thong, cami top and black thigh highs on the bed along with black dress.
I kissed Jake’s cock again then moved to each guy and lowered their shorts. I am not sure who was first but it wasn’t Troy, Jake or Sam. Jake was in front of me with his soft cock in my mouth when I felt someone penetrate my opening. His cockhead popped in followed by him roughly jamming the rest of his long hard thick cock all the way until his huge balls were touching mine. It had been over a week since I came last and with all that happened today it felt like I shot a gallon of come into Sam’s wonderful mouth. When we broke our kiss and swallowed the savory mixture of come and saliva I asked Sam, “Could I please suck you now?”
Both Gary and Vern laughed as I took a sip and said, “You are right about that Gary, I am a girly little sissy and I enjoy sissy drinks. I sucked on his monster cock getting it real wet, then leaned in and took his thick meat all the way down my throat until my nose was on his hairless pubic bone and his balls were on my chin. Gary said, ”Come here my sweet little girl,” as he bent down, cradled my face in his hands and kissed me full on my cum soaked mouth. Vern had slid under me into a sixty-nine position and took my ever so hard tiny skinny pee pee into his mouth.
Bernie and I were standing side by side now, holding hands when Mrs O got closer and said, “Want it or not you will show off!” She gripped my string and pulled the waistband apart and stroked my cock as she roughed Bernie by his neck and ordered him to kneel and look at my big, beautiful cock. I took my cock to Bernie’s hole and wanted to take him but my foreskin was pulled back and it started to hurt but Bernie kept pushing his ass back asking me to fill him.
On my first visit there alone I was very embarrassed and when I finally chose a movie to watch I had left the door slightly opened (so passers-by would know I wasn’t doing anything ‘naughty’!) A man had opened the door and asked to join me. When the second man came in, locked the door and offered a blowjob I just said ‘no, let me do you.’ Surprised he consented and I eagerly went down on him and he gave me a hot mouthful of cum in return! I would look out the crack in the door now and then, wondering where he had gone … looking for his return … while playing with my hard cock through my opened jeans.
I stroked myself and showed my ass and offered my mouth for cock, but I hadn't once considered kissing another man. I got my cock pointing up and was ready to just rub against Pete for a while, but my hand was there and his cock was there and his mouth was on mine and I was hot for him and it just seemed like the right thing to do... Pete unashamedly stroked his cock while he watched and answered my dirty talk with dirty talk of his own. Then he pulled me slightly and I looked down and watched as my cock went into his mouth. "I want your cock, Pete," I said, and started lowering myself onto him.