My first Cross Dresser and me

By Toby

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Tags: cross dresser, crossdressing

Added: 08 Jan 2007 Views: 25024 Avg Score: 4.56

My first cross dressing experience
I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said she wanted me to fuck her.

I started kissing her neck and started down her soft body, I raised her bra to expose her nipples and sucked them up hard and continued down. I stopped at her clitty and kissed, licked and sucked at it for several minutes before taking each ball into my mouth and sucking gently. As I was doing this I slowly and gently spread her legs pulling her ass off the bed ever so slightly. When I saw her ass pussy peeking out I slowly ran my tongue to it circling slowly. Toni let out a loud moan and I just planted my lips around it and started tongue fucking her slowly. She began raising her ass from the bed to give me better access and I told her to roll over.

I got up long enough to get the lube from the nightstand and laid back down behind her. I wanted her to be very excited for this so I spread her ass cheeks and again went down on her fine ass pussy, tonguing her for several more minutes before asking her if she was ready. She said she was, but to be easy as she was still a real man virgin. I raised to my knees as she did also. I placed a large amount of the lube on her ass pussy and began rubbing it around, inserting my finger slowly, just a little at a time. Toni talked about how hot if felt and I told her it was the heating lube. I continued this for several minutes until I was fucking her deeply and began inserting two fingers, this took awhile but was exciting me so much that I was already dripping. I asked her if she was ready and she said yes. I took another large amount of lube and lubed up my little, very hard clitty.

I placed my clitty at the entrance to her ass pussy and began pushing slowly. I had to hold it in place but continued to push when suddenly my clitty was inside. I slowly be began pushing and was all the way in as she moaned for me to stop. Toni asked me to just stay like I was and I did. After a minute or so she began moving her ass from side to side and then told me to fuck her like she needed. I started slowly, not wanting it to hurt too badly. Her ass started keeping pace with me and soon we were fucking each other. I grabbed hold of her hips and started stroking with a purpose, and that purpose was me, I was about to cum. I told Toni I was about to cum and she said to cum inside her, and to come deep inside her. I did as I was told, when I felt the cum reach the top I pulled her hips to me until I felt my balls on her ass and then let go. I must have cum at least 8 or 9 times. It was wonderful.

I rubbed the small of her back and squeezed her ass cheeks as I pulled myself out. Toni fell onto the bed and I rose to go and get some warm washcloths to clean us up with. I cleaned myself and then took my time cleaning Toni slowly and softly. When I was done we both drank some soda and cuddled for a few minutes before I kissed Toni and told her it was my turn. I knew it was going to be good because her little clitty was already rock hard and dripping wet.