Wife Left Me so I Could be a Girl

The bra cupped my breasts perfectly and I noticed my nipples getting bigger and pushing against the bra right before my eyes. I had a slight gasp and caught my breath. I was wearing a perfectly fitting bra and panty set. I found a pink full slip and put it on and finished off my outfit with a garter belt and a pair of nylons that felt like they were custom made for me. I stayed dressed as a girl all day wearing nothing but lingerie.

That night I went to the closet, selected a nylon and lace pink nightgown and put it over my lingerie and went to bed as a girl. I quickly fell asleep and woke up two hours later with the hardest erection I had ever had and a pair of nipples that were so huge they pushed up through my training bra and my slip and my nightgown. I flicked at them with my fingers and in less than a minute I felt like I was going to pee the bed. Instead my little hard erection jerked in my panties and I ejaculated for the first time in my life at age 23. I ejaculated without touching my little dick, and the semen poured out of my cock and soaked my panties. I was groaning with delight as I filled my panties again and again with my little squirting cock. It was a wonderful feeling and a relief to me as I proved I could ejaculate which was something I was not certain up until that night that I could do.

There was no way I was going to donate my mother's extensive lingerie collection as I fit into it perfectly, but at the same time my thoughts turned to wanting to have sexual intercourse with a biological female. I spent the next several months looking for a girl to date and I found a beautiful one in a church group I had been a member of for about three years.

Sharon and I began dating and in a very short amount of time found ourselves at that moment when we each wanted to have sex with the other, but both of us were virgins. In what was a surprise to me, Sharon took the lead and said she wanted me to be the first man to "fuck her deep" and she wanted me to do it tonight at my house as she lived with her parents. Sharon was two years my junior and was just about 22 the night we both stripped naked and got into bed with the sole intent of having intercourse.