Losing my crossdressing virginity
This is the true story of my first time with a man while fully crossdressed.
I answered an ad in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before agreeing to meet.
I took the bus to where we had arranged to meet, it was a flat in a not great area of town. Nervously I rang the buzzer and entered the block, getting the lift to the fourth floor I went to the door and rang the bell.
The door was answered by a man in his early fifties of middle eastern appearance who showed me into the flat and told me he was married and this was a friends flat he was borrowing for the day and I assured him I would be discreet. He showed me into the bedroom and left me to get ready. I took off my clothes and put on a red satin bra with black lace trim matching suspender belt and pulled my seamed stockings up my freshly shaved legs, I then pulled on my matching satin panties, I then put on my black chiffon rah-rah skirt and cream satin shell blouse with a black ribbon at the neck and did a little dance in front of the mirror to see how the skirt bounced and floated across my bottom.
By this time the man I had met was starting to get impatient so I hurriedly put on my make up with lots of red lipstick as he'd asked and my long blonde wig.
I was now ready for him.
He told me to sit on the end of the bed and stood in front of me and unzipped his flies, my whole body was trembling through excitement and nerves as he pulled out the thickest cock I have ever seen, not long but a huge girth, grabbing it with both hands I rubbed it gently until it started to get stiff,
"Put it in your mouth." He ordered me.
So I did, licking the tip first I could taste his salty juices taking more of it in my mouth I could feel it getting harder and harder and smell his musky balls bouncing around near my chin. After a while my jaw began to tire due to the massive size and I tried to pull away but he grabbed the back of my head pushing me right down to the hilt which made me gag as his dick hit the back of my throat.
"To be a real girl you've got to take it like this!" he said as I pulled away and he repeatedly pushed his fat cock as far down my throat as he could.
Eventually I struggled free and said maybe he should just fuck me, but first he wanted me to lie face down so he could push up my skirt and ride my panties so he could get his cock even harder, I agreed he could. Lying face down on the bed he lay on top of me pushing up my skirt he humped away frantically, holding me down with all his weight on top of me he pulled my panties to one side and slipped a lubed up finger into my tight asshole I moaned with pleasure as he slid it in and out, after I was well lubed he pulled out his finger and still holding me down grabbed his rock hard thick cock and pushed the head between my butt cheeks I resisted at first as he wasn't wearing a condom but he held me down and kept pushing it in, after the head was inside me the pleasure of having this wonderful big cock in me overcame any worries I had and I relaxed and pushed my hips back taking the whole thing inside me feeling him thrusting in and out was making my clitty cock hard and I got onto my knees so he could take me doggystyle and I could play with myself. After a very short time I felt his hands tighten around my waist, he pulled me hard back onto his cock "I'm cumming!" he moaned as I felt the huge cock twitching as he shot his load inside me, which then made me shoot my cum all over the satin of my knickers my cock had been straining against.
As he pulled out I felt his cum running down my thigh onto the tops of my stockings he quickly got dressed and I changed and took my make up off. We have never seen each other again.
I answered an ad in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before agreeing to meet.
I took the bus to where we had arranged to meet, it was a flat in a not great area of town. Nervously I rang the buzzer and entered the block, getting the lift to the fourth floor I went to the door and rang the bell.
The door was answered by a man in his early fifties of middle eastern appearance who showed me into the flat and told me he was married and this was a friends flat he was borrowing for the day and I assured him I would be discreet. He showed me into the bedroom and left me to get ready. I took off my clothes and put on a red satin bra with black lace trim matching suspender belt and pulled my seamed stockings up my freshly shaved legs, I then pulled on my matching satin panties, I then put on my black chiffon rah-rah skirt and cream satin shell blouse with a black ribbon at the neck and did a little dance in front of the mirror to see how the skirt bounced and floated across my bottom.
By this time the man I had met was starting to get impatient so I hurriedly put on my make up with lots of red lipstick as he'd asked and my long blonde wig.
I was now ready for him.
He told me to sit on the end of the bed and stood in front of me and unzipped his flies, my whole body was trembling through excitement and nerves as he pulled out the thickest cock I have ever seen, not long but a huge girth, grabbing it with both hands I rubbed it gently until it started to get stiff,
"Put it in your mouth." He ordered me.
So I did, licking the tip first I could taste his salty juices taking more of it in my mouth I could feel it getting harder and harder and smell his musky balls bouncing around near my chin. After a while my jaw began to tire due to the massive size and I tried to pull away but he grabbed the back of my head pushing me right down to the hilt which made me gag as his dick hit the back of my throat.
"To be a real girl you've got to take it like this!" he said as I pulled away and he repeatedly pushed his fat cock as far down my throat as he could.
Eventually I struggled free and said maybe he should just fuck me, but first he wanted me to lie face down so he could push up my skirt and ride my panties so he could get his cock even harder, I agreed he could. Lying face down on the bed he lay on top of me pushing up my skirt he humped away frantically, holding me down with all his weight on top of me he pulled my panties to one side and slipped a lubed up finger into my tight asshole I moaned with pleasure as he slid it in and out, after I was well lubed he pulled out his finger and still holding me down grabbed his rock hard thick cock and pushed the head between my butt cheeks I resisted at first as he wasn't wearing a condom but he held me down and kept pushing it in, after the head was inside me the pleasure of having this wonderful big cock in me overcame any worries I had and I relaxed and pushed my hips back taking the whole thing inside me feeling him thrusting in and out was making my clitty cock hard and I got onto my knees so he could take me doggystyle and I could play with myself. After a very short time I felt his hands tighten around my waist, he pulled me hard back onto his cock "I'm cumming!" he moaned as I felt the huge cock twitching as he shot his load inside me, which then made me shoot my cum all over the satin of my knickers my cock had been straining against.
As he pulled out I felt his cum running down my thigh onto the tops of my stockings he quickly got dressed and I changed and took my make up off. We have never seen each other again.
12年前
