First Time – Gay Sexual Stories

A crossdresser takes the next step

It was going to be just another fun night. I was finishing fitting my wig and started outlining my lips with lip liner, and followed up with some Revlon red lipstick. While not great looking, I had a great pair of lips when painted with lipstick. For the past few years, when going on business travel I always took the early flight and packed some of Brenda’s clothes so I could crossdress as soon as I got to the Hotel. I had been a closeted crossdresser for years. Tonight I was going to wear a very pretty red and black …

Wearing my favorite lingerie while camping and I get some unexpected visitors

While In college I enjoyed visiting a small state park camp ground not far from campus. The sites were far apart from one another and the trees were thick, so I was pretty isolated and out of view of other campers. I had been cross-dressing for years and enjoyed being alone in the woods where I would wear what I wanted undisturbed. I still lived in the dorm on campus and didn’t have much privacy, so I treasured my weekend getaways. As I set up camp, I had a bra and pair of panties on under my shorts and t-shirt …

A Bad Day brings about an unforgettable experience

It was a rainy and cold night when I entered the smoke-
filled bar just off the Interstate. A series of personal
defeats had sent me home for the comfort of my most
recent lover. My unexpected early arrival found her in
the arms of another and after a flurry of ill
contemplated accusations, we were soon on our separate
ways.

Fearing further confrontations, I eased my wheels into
the unimposing parking lot and with a dash of cologne
entered the dimly-lit room awash in the mid summers rain.
My full intention was to drown my sorrows in solitude and…

Am I Gay? Or What? husband seeks Gay Experience

The day started off innocently enough. I had stayed at home
to do some work on my computer away from the hustle and
bustle of the office. I slept in a little later than normal
since I would not have to put up with the commute.

My wife had already taken the kids up to school and had gone
to work herself. So, the house was all mine. I got dressed
in my usual work at home outfit of jeans and casual shirt,
quite a contrast for the usual 3 piece suits. I was
thinking to myself with all this …

A summer with his aunt, who happens to be incredibly hung

Max leaned against the windowsill of the sparsely decorated guest bedroom, staring out over his Aunty as she sunbathed by her glistening pool, laying on her back she reclined luxuriously on the sunbed, sunglasses resting across the bridge of her nose, soaking in the rays on her already sun-kissed skin. She had expressed to him earlier, with one of her seemingly trademarked smirks, her concerns of adopting tan lines and so, shamelessly, she sunbathed nude.

Max watched as she stretched out her arms, yawning before settling back, her skin warm with the sun, body slender and lithe, mature but not …

Tag: First Time