I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the feeling of her cock inside me opened up the possibility for more.
One Thursday she told me that we were going out on Friday. I said ok but did not think too much of it as we often went out Friday nights.
She then said, "Since you have Friday off you need to get dressed up as Vicky."
This made me hesitate. The clubs we went to would never tolerate a crossdresser. Although I can pass as a female when I am dressed in looks, my voice would give me away in a second. She saw my apprehension. She said we were going to a new club that is open to crossdressers, transgenders, and other alternative lifestyles. After hearing this I quickly agreed.
I spent Friday getting ready to go out. I started out with a nice bubble bath. I shave off what little stubble I had. I then painted my fingernails and toenails a deep pink. The entire day I was beyond excited. I had been places dressed up as Vicky such as shopping and restaurants but this was going to be different. By the time my wife got home from work I was teeming with anticipation.
My wife helped me with my makeup. Usually I wore it conservatively but not this time. She used heavy eye shadow and bright lipstick. By the time she was done I looked like a cheap slut.
She said, "Wow, you really look fuckable. I can't wait to see the guys hit on you."
She then fixed my hair. I had picked out a tight pink dress to wear for the night. Underneath I wore a hot pink thong and matching bra. I also chose to wear a garter belt and stockings. I put the dress on along with matching 5 inch platform heels. When I looked in the mirror I was stunned. I had never looked so sexy or slutty. I was ready for our night out.
When we got to the club my wife paid the cover charge and we found a table. A waitress came over and took our order. I was amazed to see the waitress was also a crossdresser. My wife looked at me and smiled. The waitress came back with our drinks. She then said to me,
"You look great, I love your dress."
I managed to stammer, "Thank you."
After enjoying our drinks for a while my wife asked me, "Are you having a good time?"
I replied, "Yes, this is exciting."
She then said, "It's about to get even more fun."
She had noticed a guy coming over to us and she indicated this to me with her eyes. I looked over and saw a good looking man about 6 foot approaching our table. He had dark hair, was about 30 and looked to be muscular. I assumed he was going to hit on my wife but I was blown away when he looked at me and asked if he could buy me a drink. Thank god it was dark in the club as I blushed horribly. I replied that I would love a drink. He then sat down and started talking to us. He introduced himself as Chad. My wife was smiling the entire time. After a few minutes he asked if I wanted to dance.
I looked at my wife and she mouthed, "Go for it!"
We got up and danced. After a few minutes he moved closer to me and started grinding on my hips. I thought to myself, "Is this really happening?" I discovered that I was getting very excited. I started picturing this man fucking me. Embarassed by these thoughts I looked up to find my wife. She was not at our table and in a panic I started looking around for her. I then saw that she was dancing with another guy.
She approached me and I leaned into her and said, "This is crazy, we should probably go." She asked why. I said, "I think this guy wants to fuck me."
Her response blew me away. "Why do you think we came here?" She was actually giving me permission to fuck another man.
I was so excited by this time I was actually accepting this possibility. After a few dances we sat down again. Chad sat next to me and I was thrilled when he put his hand on my lap. After a few more drinks and dances Chad asked me if I wanted to get out of there. I did not know what to say. My wife overheard and whispered in my ear, "Go, I have keys to the car, have fun and call me later." I then looked at Chad and said I would love to go.
Chad and I went outside and got a cab. We sat in the back and he put his hand on my lap. I then moved my hand onto his lap. I looked at him and he leaned over and kissed me. I got more and more excited as his tongue probed into my mouth. I moved my hand up to his crotch. I could feel he had a sizable erection as did I by this point. I rubbed his cock while we kissed. A few minutes later the cab dropped us off at a hotel. Chad and I walked to his room holding hands.
We got in the room and closed the door. Chad looked at me and said, "I want you so bad." I replied by grabbing him and kissing him again. As we kissed I moved my hand down to his crotch. I rubbed his massive cock through his pants. He was rubbing my ass and moved a finger towards my crack. I then undid his pants and zipper. I could now feel his rock hard cock in my hand. Chad undid the zipper on my dress and I let it fall to the ground. He pulled his mouth from mine and whispered, "Suck my cock please, I want to feel your hot mouth on me." This was a moment of truth. Although I was very aroused, I was not sure I could take a cock in my mouth.
I decided to go slow. I started undoing his shirt and kissing his chest. I moved my mouth closer and closer to his crotch. When Chad's shirt was off, I knelt down in front of him. I pulled his pants and boxers down. Right in front of me was a very hard cock. It looked about 8 inches. I started stroking it and then I leaned forward and licked the tip.
"Oh yes," Chad said. This encouraged me to take him in my mouth. Slowly I wrapped my lips around his cock. I could feel the heat from it and smell his scent. I started to move my lips up and down as my wife did many times. This was getting me very aroused.
"God yes that feels so good. Suck my dick," said Chad. I was enjoying the sesation of his cock gettting harder and bigger in my mouth.
Chad started thrusting his hips faster. "Fuck yeah suck that dick!"
Knowing that I was making him arounsed like this was so erotic. My own cock was harder than it had ever been. "Fuck yes I am going to cum," screamed Chad. I kept my mouth on his cock. At this point there was not longer any hesistation from me, I wanted him to cum in my mouth. I wanted to feel it spurt, I wanted to taste it.
"Oh god," Chad grunted. I then felt the first spurt of his cum in my mouth. I started sucking on his cock. Spurt after spurt of his hot cum crossed my tongue. I held it in my mouth for a moment and started swallowing. I felt so wonderful going down my throat. I found myself moaning like a slut as I swallowed his cum.
When he finished cumming I stood up and Chad kissed me. He probed his tongue in my mouth and tasted the remnants of his cum. "Wow, that was wonderful," he said.
I said, "I hope there is more where that came from."
He said, "Yes just give me a few minutes."
I went to the bathroom to freshen up. When I came out Chad was laying on the bed. I went over and kissed him. I reached down and started stroking his cock. It did not take long for it to get hard again. By this time I wanted Chad to fuck my ass desperately. I moved on top of him in a 69. I took his cock in my mouth. Chad started suck on my cock as well. It did not take long and he was hard as a rock. I looked at him, smiled and said, "I want you to fuck me."
He reached in his bag and pulled out some lube. I took it and rubbed it on his cock. I felt a cold sensation as he put some lube on my ass. Chad then started probing a finger inside me. I sighed at the feeling of his finger moving inside me. After a few moments he worked a second finger inside me. This hurt a little but I foced myself too relax. It did not take long and he had my anus ready for his hard cock.
I got on my hands and knees with my ass spead as far as I could. I could not wait to feel his hard cock inside me. Chad kneeled behind me and moved forward. I could feel the head of his cock touch my sphincter. I moved my hips back to him as he started to push his cock into me.
My wife had fucked me many times with her strap on. None of that prepared me for Chad's cock as he entered me. My ass felt on fire and I thought he was going to split me in half. Chad noticed this and stopped pushing, allowing me to relax. After a few moments, the pain subsided to be replaced by the wondeful sensation of having a cock in my ass. Chad started thrusting in to me saying, "Fuck yes your ass feels so tight." He grabbed onto my garter belt and was humping me hard.
God it felt so good, his hard cock moving in and out of me. His cock was teasing my prostrate. Chad would fuck me slow and then fast. It was heaven feeling his cock in my ass. Chad then stared to quicken the pace. I knew he was close to cumming.
I said "Fuck yes, cum inside me I want to feel it." With that Chad grunted and my ass started feeling warm and wet as he filled me with his cum. Chad kept his cock in my ass until it got soft and popped out. I then turned around and kissed him again.
I got up to go to the bathroom and his cum leaked out of my ass and ran down my leg. I scooped it up on my finger and tasted his cum again. I then got dressed and left his room, feeling like a total slut at having a one night stand. I called my wife and said I was coming home with a wonderful story along with a bellyfull and ass full of cum.
My wife said, "That's great honey, I have another surprise for you when you get home."
"What is it," I said.
Her reply was, "You will have to wait and see."
And so will you.
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<a href="https://www.lushstories.com/stories/crossdressing/vickys-first-time.aspx">Vicky's First Time</a>