Gay men's rec center donor uses money to gain access.
"Jen, I don't know. I feel weird."
"Hmm, this is interesting," she said pensively, "I've been thinking that I would be the one backing out of this, not you. To be quite honest, (and I'm surprised too), I find this whole thing kind of erotic. No, more than kind of."
She stood back and abruptly strode over to the closet where she donned a bath robe, "Maybe this is going too fast for you. Let's slow it down, take our time, have some more wine. Maybe we won't even make love tonight; I just want to explore this okay? Come over here baby."
She motioned for me to sit at the vanity mirror while she opened some drawers and sifted through the feminine accoutrements of makeup.
"Do you know how to do makeup at all?"
"No," I said, "I've only worn women's clothes. Thought about it, but I really didn't have a clue about it."
"Okay, let's have some fun then okay? Experiment a bit. I'll get us some more wine first, so just relax."
I sat there at the vanity feeling very strange, like I had been transferred into another dimension. It was not altogether unpleasant, just bizarre, as any heterosexual cross dresser would feel I suppose, at least one who had not ever come to terms with their identity. I felt my legs, so smooth in the nylon, and the skirt was slightly stretchy so that it pulled my legs together in a very feminine way. The bra was tight, maybe a bit small, as it cut a bit into my midriff, and the straps were forming a groove on my shoulders. The socks that gave me breasts presented a slightly lumpy appearance, and while I waited, I pulled them out and rearranged them so they were more smooth and natural looking. Jen came in just as I was feeling my "breasts".
She laughed, "Jackie, a lady never feels her own breasts unless she desperately wants to get intimate, either alone or with a lover. Here's your wine. Now drink and relax."
"Yes, ma'am," I said, and laughed.
"Okay, let's have some fun." She spun the chair around away from the mirror and stared at my face for a long time, thinking, "Well, I see we won't need much blush, will we?"
My face was burning up with excitement, embarrassment, perhaps humiliation too...just, well...just many things. I sipped my wine whenever I could in between Jen's art work on my face...the foundation, the mascara, eye shadow, lipstick. It seemed to take a long time, but actually it lasted only two glasses of gulped wine. Finally she said, "Well I wish we had your wig, but we don't. Doesn't matter. You look great." And she spun me around to look.
I couldn't believe it. My eyes seemed so large and feminine, and my lips...I tasted the lipstick...my mouth was so...different. I made an artificial smile and glanced at Jen staring at me, her mouth open with astonishment.
"Oh my God," she said, "Oh my God! Stand up Jackie! You look gorgeous!"
I didn't. But close enough.
Our painted lips met and we crushed our bodies together, breathing heavily as we struggled to get to the bed without breaking our embrace. Once there, she unzipped my skirt, pulled it down, and then followed with a rip at my panties. Since I had put them on first, they could not be removed without removing the garter belt. Far enough. I burst out and she pushed me onto the bed while her legs straddled me, my legs held together by the panties. We were in full lust, and she mounted me easily, yelping sweetly as there was no resistance, lubrication not an issue. I thrust wildly as she did the same, and then she slowed it down, saying, "Slower Jackie, slower, yes, yes, okay, good...yesss, oh God."
She had her hands on my ""breasts" as she pumped up and down on me, occasionally leaning over to smear our lipstick together.