First time Crossdressing

I needed to relax for his shaft and gland head to slip pass my anal sphincter muscle. I relaxed more with Ray being able to insert his erection halfway into my man-cunt. I was tight and there was no lube; I had to reach behind me and spread my cheeks. With a last push, he was all the way in. Ray started to thrust in deep then slowly withdrawal.

He grabbed my bra began to squeeze, pinching my nipple at the same time. I tighten on his member inside me, gave him pleasure. The speed picked up; the thrusts were deeper, and each time I cried a moan of pleasure. Ray held my hips, so I could not move, and he climaxed was way up inside me. Everything happened so fast that I did not realize Ray did not wear a condom.

I collapse on my side, Ray rolling with me, his manhood still inside me. We lie there for a few minutes, when his relaxed cock slipped out of my now dripping wet anus. He patted me on my butt and said I was hot in pantyhose. He started to dress, mentioning that he had nothing to eat. He told me to stay dressed. I went to the bathroom to go clean up. I kept the stocking on, put the panties back on and wore the bra; I was dressed as a sissy under and a guy?s clothes outside.

We drove to a restaurant with my sissy thing under my clothes. We had a pre dinner drink, another dinner drink during dinner, and an after-dinner drink. Ray made comments about being able to see my red bra through my shirt, and the man at the bar was looking at me. Ray was joking, but I still felt humiliated and self-conscious about being dressed. Ray would say I was dressed in sissy clothes, and that it suited me. During dinner, Ray went on how sexy I was; he said I was an enjoyable lay.
After dinner, I was thinking I would go home, but Ray asked, "Do you want to come back to the motel room?"

Well, the story continues; we returned to the room; we did what we did before. I fell asleep and may be I felt Ray in me one more time, or it might have been a dream. The next morning Ray woke me with his morning woody; he used me again. I left the motel tardily in the morning, went to my place, cleaned up, and was two hours late arriving at work.

I received a text message from Ray, I have extended my stay another night, I want to meet you tonight.
I sent a text message back; sure, what do you want me to wear for you this time?