Crossdressing Memories

by Dan (CA)

Brendan looked down at the eye shadow and makeup he had impulsively bought at the drugstore. He had been divorced for six months now and had been feeling suitably bored. He really hadn’t any desire to try starting dating or to do much.

Then, from the back of thoughts came his memories of when he had been younger, fourteen at the time. It was kind of crazy, but he had started enjoying the fun of cross dressing.

He didn’t know why he had done that exactly. He had no desire to be a girl. He liked being a boy. Yet, to dress up and play at having this female guise had been such a turn on.

He had tried using some of his mom’s makeup and was surprised by the results when he looked in the mirror and saw that he made quite a cute girl.

So he had experimented with that a few times and then got more daring and painted his toenails red. That had given him such a terrific boner, which he had delighted in jacking off – twice and in fairly quick succession.

It had been so much fu that he had started doing that regularly that summer while his mom was at work. Always being sure, or course to remove any traces of his playful indulgence before she got home.

On several occasions, feeling particularly daring, he had actually worked up the courage to venture out that way in his girl guise, thrilled by the boners that never failed to give him. Only, he was so afraid of having his secret discovered, he had been intimidated to do more.

Now, years later, remember his past fun, he had impulsively bought some make up and nail polish and a brunet wig. Taking his time, he reacquainted himself with putting on the makeup and painting his toenails. It was fun doing that, and even a little thrilling.

Looking in the mirror he found that the cute girl that he had transformed into all those years before, was still there waiting for him. He was pleased and delighted by the results.

He was wearing a gray striped t-shirt and gray hoodie and jeans.

Brendan slipped the jeans and his underwear down and off, revealing his reassuring maleness.

As he stood there, his penis began to grow, curving off to one side until it became sufficiently stiff to swing boldly upright.

He smiled and took it in his hand and began to stroke its hard length. God, that felt so good! It was fantastic doing this pretending to be a girl!

Suddenly he was ejaculating, his dick sending several long streams of his white cum flying through the air to land several feet away, splashing on the bathroom floor in a white overabundance.

“Oh, yeah … yeah ..” he panted as his cock throbbed repeatedly and with satisfaction.

It was so good cumming like that once again in his girl disguise. It was such a turn on!

As he finished he was already wondering … did he have the nerve to start venturing out that way? It would be a real turn on, he knew, and he decided – yes. He would try it!