My name is Kevin, I’m in my 20s and I live in the southwest United States. I keep myself in good shape after having played a lot of sports in high school. I’m about 5’8 tall and weigh 165, I’ve got brown eyes and light brown hair and I’m mostly hairless on my body. That last fact used to bother me a lot, especially when I was at the beach or in the locker room, but no longer. Why? Because I’m bisexual and a cross dresser.
When I’m a man, I’m a man and I enjoy the ladies’ company. And when I am Ashley, I’m all girl.
I became Ashley at 18. I had never been with a man before, however I’d often fantasized about it and those fantasies made me realize that I was bi. I told all my buddies and my girlfriends. The ones who mattered knew and didn’t care and treated me no differently than they had before I told them. The ones that didn’t…oh well.
One night I was out with my buddies at a local watering hole and we had been drinking beers all night. I know shame on me for underage drinking, but it turned out to be one of the most important nights of my life. It was life changing as a matter of fact.
A very nice looking man came to our table and sat down right next to me. He was a doctor and knew us all pretty well from playing basketball at the Y. Even though he was about 20 years older than we were, he was a good player and was in excellent shape. I remember seeing him after the games in the shower and noticed that he had a nice big cock. Of course, I didn’t want to stare, but many times, I just couldn’t help myself. I would stare at it when I knew his eyes were closed and wouldn’t catch me. It was so big soft that my buddies and I would always comment on it amongst us on the way home from the game. I never said much, but I sure did fantasize about it a lot.
So, I was extremely happy when he came into the bar, walked across the room to our table and then sat down right next to me. My heart was racing, because of the beer and mostly because of his nearness. Sometime during the course of the evening, he brushed his leg against mine and kept it there. I didn’t move my leg away, which emboldened him to reach down and put his hand on my thigh.
I looked at my buddies, and then looked my doctor friend in his deep blue eyes. He returned my look with an intensity that I had never seen before, then moved his hand higher up my thigh to where my hardening cock was.
He squeezed it and held it and I felt the rush of blood to my cock and to my face. For the first time in my life another man was touching my cock. I was blushing and I was excited and I was getting bigger in his hand. I looked back at my buddies to see if they saw, but they didn’t. They just kept listening to the loud music and drinking their beers.
The doctor leaned over to whisper into my ear, allegedly because of the noisy bar. And I knew what he was going to say and I was nodding affirmative even before he said anything.
He asked if I want to go for a ride with him.
I yelled to my buddies that Doc was leaving, that I was tired and he was going to give me a ride home after I finished my beer. They nodded and cheered me with their beers in acknowledgment.
The doctor removed his hand to give me time to let my hard-on dwindle.
After I got more comfortable, we finished our drinks and walked out to his car – a really nice German luxury car. I got into the passenger seat, he slid in to the driver’s seat and we drove away. I couldn’t believe that I was getting picked up by the guy that I had fantasized about. I really wanted to lean over and feel him the same way he felt me, but I was too bashful to be so forward.
Doc stopped at a local gas station that had a fine supply of porn magazines and beer. And he told me to wait in the car.
“I have a surprise for you,” he said as he shut the car door.
He walked in, greeted everyone, smilingly and then disappeared behind the door where the porn was on display. He was in there for a good 5 minutes, which seemed to me like an eternity.
He came out with the beer and a brown paper bag, which contained what looked like about 4 porn magazines.
As he was getting in the car, he put the beer in the back seat and handed me the magazines. I looked at them and they all had the same theme. They were all about cross dressers and men cumming on them – cumming all over them. Some were group shots and others were just one on one sex.
Doc told me, “I really like my lovers to be men, but I really get off on men dressed up as women. Would you like to try that?”
I stammered my answer, “I’ve never done anything like this before.”
“So you’re a virgin?”
“Well, no. I’ve been with girls before,” I answered.
“Never with a man?” he asked.
“Not even circle jerks or blow jobs?”
“No,” I answered and then sat there quietly.
“Oh, Kev, that doesn’t bother me at all. In fact, I am looking forward to taking your virginity. You’ve seen me in the shower, I’ve seen you staring…” he said and smiled a warm smile at me.
He continued, “And I’ve thought about you a lot. I like how you look now, and I think I am going to love how you look as a woman.”
“Thanks,” I said.
We had pulled into the parking lot of the local adult store, where there was a lot of sexy lingerie on display.
“Wait here, Kev. I’ll be right back – with more surprises.”
After about 10 minutes, he came out of the store with one rather large bag, which he put in the back seat of the car with the beer.
“May I see?” I asked.
“Not right now, Kev. I’ll let you see when we get to the hotel.”
“Well, yes, my dear, how else would a gentleman take a young lady’s virginity?”
We drove the rest of the way in silence. My mind was racing and I was nervous in anticipation as to what was going to happen. I was hoping all my fantasies were going to come true, but I never imagined doing them as a woman.
We arrived at the entry to the hotel, Doc left the car running, pulled out a hotel pass key, grabbed the bags.
The valet said, “nice seeing you again, Doc.”
We walked past the concierge who nodded a pleasant greeting, which was returned in kind. When we entered the elevator, no-one was in there.
“Kevin, this will be the last time I call you Kev or Kevin,” Doc told me. “I want you to pick out a name that you’d like for me to call you whenever we get together.”
“I really like the name Ashley.”
“OK, Ashley. From now on you are Ashley. I like it. It’s really feminine.”
The doors opened and we walked to the hotel room, which was not a room, but a suite. It was extremely nice. The best hotel room I’d ever been in. I felt special.
Doc handed me the bag from the adult store and said, “this is for you. Happy birthday.”
“It’s not my birthday,” I said.
“No, it’s not your birthday, it’s Ashley’s.”
Just then there was a knock on the door. Doc opened it and a lady came in with a cart that was loaded with all kinds of items that I recognized from my mother’s supply, but had never used before.
“This is Marlene; she’s an esthetician and will take care of you. Please do as she asks. She’s really the best there is. I’ll see you in a little while.”
Then he left.
Marlene was all business. She took the bag from me, set up a table for me to lie down on, turned her cart a little beauty shop and told me to take off all my clothes. The way she said it told me that she had no interest in me sexually at all. She instructed me to sit in the chair in front of the mirror she had just set up and then clipped my hair. It was the shortest I had ever had it. I thought about my friends and what their reaction would be.
Then she pulled out a wig, put it on my head and styled it. I had to admit that it was really nice. She plucked my eyebrows, and then she clipped my pubic hair as short as possible and asked me to lie face down on the table. She waxed and bleached my ass, which wasn’t as unpleasant as I thought it would be. She then asked me to flip over and waxed my pubic region, my legs, my armpits and what little hair I had below my belly button.
She told me to go in the bathroom, take a shower and shave my face and handed me an enema. And she instructed me to come out naked when I was finished.
I figured the faster I was finished, the faster she’d be finished and the faster Doc would be back. So, I decided to take my time.
When I came back, she put on my makeup and did my nails. They were red and acrylic. She grabbed the bag and helped me get into my new outfit – all matching – stockings, a garter, panties, a corset with built in falsies. Then she finished me off by putting on the wig.
I looked stunning and felt so beautiful. I was all girl.
She texted Doc, handed me a card and told me I had an appointment for hair removal next week. She started to leave.
I said to her, “may I ask you a question?”
“It seems like Doc as done this before. Does he have other lovers?”
“No. He had one lover recently, but she left to go to school. She told him that she wanted to be a boy in college and broke up with him. He was devastated. He’s been looking for someone for a few months now. Doc is a great guy. Do not break his heart.”
“You better not, Ashley,” she warned and walked out as Doc was walking in.
Doc looked me up and down and said, “wow!”
I blushed for about the third time in 2 hours.
“Turn around and let me look at you.”
I did as he instructed.
“You are a vision of red loveliness. I knew you’d look so sexy in red. You have the sexiest ass. I haven’t seen an ass like that in a long time. And your lips. Those luscious lips. I want to taste them.”
He came up to me, put his arms around me, and then kissed me. Another man was kissing me for the first time and I let him. It was gentle and I was a bit tentative. But soon I warmed up to it, opened my mouth and he inserted his tongue in to mine. With his strong hands, he pulled me closer, and then slid one hand up to my head and the other down to my butt. And then he kissed me even harder.
I was on fire. I was excited about receiving my first man/man kiss. Actually it wasn’t. It was my first woman/man kiss.
My hand was on the move next. I slowly moved it down his body to get to his cock -that big spectacular cock of his. I wanted to feel it getting hard in my hand.
He had other ideas, though, and told me, “no my sweet. Not just yet, OK?”
It was agonizing, so I pouted and then he removed my put with his lips.
“I’ve been wanting to do that for a long time,” he whispered to me, “I want you. And I want you right now.”
He took my hand and led me over towards the bed. My cock was semi-hard and bulging out of my red silk boy shorts. I thought it was pretty funny that he bought me my first pair of panties and they were boy shorts.
Doc stopped just short of the bed, turned me to face him, then reached down to feel my cock through the silky sexy panties. It was growing in his hand and I wanted my penis to be released.
“Please, Doc,” I whispered, “please take off my panties.”
“Me, first,” he said, as he started to unbutton his shirt.
He was tantalizingly slow. He undid button by button starting from the top, revealing his sculpted hairy chest. I reached over to feel his chest after his shirt came off and it was spectacular. I rubbed him all over while he was undoing his belt and unbuttoning his trousers. I noticed that he was not wearing any undershorts, nor was he wearing socks. It was so sexy to see the top of his cock peeking out from his pants as he unzipped his zipper.
He was so thick. It was quite a bit thicker than the dildo I had been using to masturbate and I was hoping that he could fit inside my ass.
Finally, he let his pants fall to the floor and his magnificent man meat stood at attention. I sucked in my breath as I saw it and immediately grabbed for it. I wanted it my hot little hands. I wanted it in my mouth. I wanted it in my ass. And I wanted him to shoot his cum all over me. I wanted it all.
He grabbed my hand and said, “not yet. We have a lot of time. I want to take care of you first. I want you to cum first. After all, a gentleman knows that ladies always cum first.
With that, he reached down and pulled the shorts over my hard cock. And then he lightly touched it.
“I’m sorry I’m not as big as you are,” I said to him.
He gently pushed me onto to the bed, laid down next to me, pulled my cock up to his lips and said into it, “shhhh…you have a nice cock. I love the size of it. Not too big at all. I love it. And it is so hard.”
He softly ran his fingers up and down my cock. I looked down at his and his cock was standing straight up. It looked to be at least 10 inches long and it seemed to be just as thick. Or maybe it just looked thicker because I was concerned about it being in my ass.
“Ashley, this is your first time and I will be gentle, so just lie back, relax and let The Doctor take care of you.”
I did as he told me and then I felt his hand reach to the base of my cock and softly grasp it. Then he started jerking me off. He was taking his sweet time, making me harder than I had ever been. Then it happened. He licked me on the underside from the base to the head of my cock. I twitched from the sensation. And then he did it again. And again. And again. I was so fucking horny by this time, I wanted him to stop licking and start sucking.
He sensed that that’s what I wanted and he put the head of my dick into his mouth and swirled his tongue around the crown. Then he opened his mouth wider and went down on it. Slowly. Until the entire length of my penis was all the way in is mouth and down his throat.
The feeling was incredible. My first fantasy about him was coming true.
He pulled it all the way out of his mouth, then deep throated me again. Then he did that again. And he was stroking the base of my cock as he lowered his mouth onto me. It was amazing. I had to see it. So I lifted my head to watch my new found lover sucking my cock all the way.
I was still dressed in my garter, corset and stockings and this incredibly gifted cock sucking man was giving me the most spectacular blowjob of my entire life.
I laid my head back down and moaned at him sucking me.
He pulled my dick out and said to me, “tell me want you want me to do, Ashley. Tell me what you want.”
I started talking dirty to him, “suck me, Doc. Blow me, lover. Take my cock. Take it all the way. I love the way you are sucking me. Make me cum. I want to cum so hard in your mouth. Deep throat me. Oh my god, Doc.”
“Call me a cocksucker, Ashley.”
“Oh you are a cocksucker, Doc. You love to suck my girly dick, don’t you? You are a dirty little cocksucker and I want you to take all my cum in your mouth.”
His mouth was smooth, wet and hot on my cock. I was so close to cumming.
I told him, “holy fuck, Doc. Keep that up right there. I am so close. I want to cum in your mouth. I want to fill your mouth with my cum. I want it right now.”
I felt the surge of cum start from the depth of my balls and work its way up my cock and into his mouth. He held me down with his strong hands with my cock all the way in his mouth. I spurted about 6 or 8 shots of cum down his throat as he held me there. I couldn’t move.
“Oh fuck, Doc. Please. Please stop. Please take my cock out of your mouth. Please, lover,” I pleaded with him.
Finally, he released me. My cock popped out of his mouth and he let me go.
Then he did something that was something I hadn’t fantasized about. He climbed up to me, kissed me on the lips, opened his mouth and gave me my own cum.
I was spent. I hadn’t cum like that in a long time, if ever. It was the best blowjob I had ever had. I wanted to shut my eyes and go to sleep, but Doc had other plans.
He took my hand and placed it on his cock.
“Here you go, baby. Feel it for a little bit.”
I looked down at the monster in my hand. I had only felt my own dick and his was substantially bigger.
“Do you want me to suck it?” I asked tentatively.
“Yes, I do, but only as a prelude to me taking your virgin ass.”
He propped himself up with a pillow behind him and I knelt in front of him and started licking him the same he licked me. In my inexperience, I figured the best form of flattery was imitation. I did that the same amount of times that he did it to me, and the last time I licked him, I went as slow as I could possibly go.
I looked up at my big handsome man. His eyes were closed and his head was back. There was a slight smile on his face. When I got to the top of his penis, I stretched my jaws as far as they would go and inserted the first penis I would ever taste into my mouth. I swirled my tongue around the crown just like he did to me.
I felt like I could do that forever. I was content to lick the head for an eternity. I guess I must have been lost in concentration because I heard a camera click and looked up right after I heard it. He was holding his iPhone and grinning from ear to ear.
“Do you want to see what you look like with my dick in your mouth? It’s pretty fucking sexy.”
He turned the camera around and showed me.
There I was. Ashley. I was a girl on my knees with a monster cock in my mouth. I was never so amazed at anything in my life.
“Oh my god,” I exclaimed, “I can’t believe that’s me!”
“That’s you, baby, and you look spectacular like that. I’ll text it to you after. OK?”
“OK. Next time I want to pose for you.”
“Hmmmm, Ashley, I’d like that,” Doc said, “but now, it’s the time you’ve been waiting your whole life for.”
I felt a twinge in my cock and I knew what he was talking about.
“Reach into that nightstand drawer and pull out the condoms and the KY, my little slut. I am so ready to take your ass.”
I did as I was told. Magnums. Of course. And warming KY jelly.
He was sitting there, smiling, and stoking his cock.
“Come here, Ashley,” he said as he patted the bed.
I sat right next to him and he replaced his hand with mine.
“I’m super hard right now, as you can tell. I am so fucking turned on from sucking your cock and you licking me. I could take your sweet ass right now, and fuck you hard, but I don’t want to hurt you. I want you to relax and enjoy the next sexual experience. That’s why I sucked you off until you came first.”
“I love how you are stroking my cock right now, but I need to fuck you. Open up the condom and roll it down my cock,” he said, taking control.
I tore open the package, opened up the condom and slid it over his massive schlong. I didn’t think the condom would fit, but it did.
“Now, hand me the KY and get on your hands and knees. Get as comfortable as you want. I want to take you from behind first. Then we’ll see how you like it that way.”
I complied. I could feel his hands on my ass. I felt him open me up like a ripe piece of fruit. I felt my ass become exposed to him. Then I felt his hot breath. And then I felt his tongue. He licked my freshly cleaned, waxed and bleach rosebud. It felt sensational. He licked me from my ass to my balls. Then back again. I loved that feeling. He stopped at my hole, slipped his tongue in, then reached up to fondle my testicles. His hands were warm and his tongue was hot.
“Do you like that?” I heard him ask.
“Yes, Doc. I love it.”
He licked me again – slowly and sensuously. I stayed on my knees, and moved my hands to my own ass. I pulled my ass cheeks apart, exposing myself to him. I was face and shoulder down on the bed with my tight pucker hole opened up to him.
“That’s it, sweetheart, I love it,” he complimented me.
Then I felt something cool on my asshole. And it warmed up. It was the lube. It felt so nice. I started to do relaxation breathing in anticipation of what was coming next. He dipped a finger in my butthole and then started fingering me. Then he slipped another finger in. He had two thick meaty fingers in there. I tried to open myself even more.