Alone With A Sissy

Home alone with the wife conveniently out of town for the next four days, Mark wanted badly - badly - to act on his urges to be intimate with a man, to hug, kiss, touch, rub, stroke, suck, the whole progression of lovemaking. He was starting from scratch, as his gay friends also were his wife's friends and he didn't want to take a chance that a careless word might slip.

(He found it humorous that his wife had an affinity for gay men and claimed she had highly developed gaydar, when her partner secretly longed to have gay sex and for years had been feeling the cravings he was feeling tonight.)

Mark wanted the hookup on his own terms. That meant at home, his or the other man's, in bed, not a car in a poorly lit section of some park or a rest stop on the interstate. So he did what he believed to be the only thing he could do: troll Craigslist for a man looking for the same thing he wanted.

It was midafternoon, after he'd dropped his wife at the airport, and he sent messages to a half-dozen men who he thought he could turn on. To try to seal the deal he attached a photo to each message: one showing him lying on his back, grasping his erect dick, another showing his whole fat body in the woods in a park an hour from his house that he'd taken in the summer. In fact he had been sending that and other pictures from that memorable afternoon in the park to many emails before now. There were some response but no meetings, and that's how it was going tonight.

Okay, screw it, Mark thought to himself as he checked his inbox for the tenth time and saw nothing for a tenth time. I have to do something about this horniness enhanced by several ounces of vodka. I'll dress up.

He went upstairs to his bedroom closet and removed his sweaters from a shelf to reveal his treasures in a shopping bag. Emptying the bag on his bed, Mark admired his women's underwear:

- the first thing he bought, a Playtex 18-hour longline bra with a dozen snaps that he'd gotten at a thrift store. (He had lied to the clerk that he was in a play and had to dress as a woman.)

- black pantyhose and beige pantyhose discarded by his wife. Easy. Never mind the runs.

- a black front-close brassiere and silky black panties he had bought brand-new at a Target in the middle of the night with no one around to see him in the lingerie section. He ran it through the self-serve scanner and no one was the wiser. He never washed anything because he liked the smell from his groin and the panties would become stiff with dried semen over time.

- red low-cut panties he had found in a parking lot, the tag still on it. I must have been meant to have those panties, Mark thought to himself.

- a light-pink bra he found in the street! How was all this women's underwear showing up outside, discarded? One of the straps had broken; he would fix it with a safety pin.

- his favorite, a beige padded bra bought during another late-night run to Target. He loved the way it held his man boobs just so, as if it had been fitted to him.

- a black garter belt and black thong bought at a store catering specifically to drag queens. He liked the feel of the thong in his ass crack but when he cut the legs off a pair of black pantyhose bought at the corner gas station and, after 15 minutes of fiddling with the clasps, he felt sexier than ever. He would take photos of himself and admire his womanly-proportioned legs without the knobby calves he'd seen on so many drag queens.

- a crucial acquisition: shoes, at a Salvation Army secondhand stre. He had managed to find a pair of woman's white size-12 shoes with one-inch heels - high enough to be able to walk in and not so low that they didn't look feminine. A bigger pair would have been easier to walk in but he wasn't going far, just enough to admire himself in the mirror and take pictures.

Mark loved his women's underwear. He was so conflicted about his sexuality, not comfortable with masculinity as defined by society and not so feminine as to stand out from other men. When he wore his women's underwear he knew where he stood. He looked like his idea of a woman, never mind the body hair or the body fat.

He didn't possess anything that had belonged to his wife. He saw her in her underwear every day and there was nothing different or forbidden or sensual about it.

But he had pushed his desires further after his mother-in-law went into an assisted-living facility and would never again wear the undergarments she had at her home. He went into her chest of drawers and took a big black bra, a big white bra, big black silky panties, plain white cotton panties and a silky black slip. His mother-in-law was a big woman and her underwear fit Mark well. He had fantasized for years about stripping that very underwear off his mother-in-law and fucking her as she gladly took his cock into her old woman's cunt, crying for more, more dick she had been denied for years by her disinterested husband. He would think of her when he pulled her panties up to his hips and snapped into place the bras that had held his mother-in-law's old saggy breasts that nevertheless formed much of his fantasy about fucking the happy old woman.

With the array of underwear spread before him, Mark would make an evening out of trying on different combinations and making photos of himself that he would admire, and masturbate over, later. His first choice was the old favorite black 38C front-close bra that his man breasts filled perfectly, the garter belt and black stockings, his mother-in-law's smooth black underpants and those tight but pretty shoes. Setting the timer on his camera, he made a half-dozen pictures of himself to file away with the dozens of others he had made over the years.

Mark didn't always end his dressup sessions by masturbating. But tonight he had read a couple of Craigslist postings from men looking for other men to dress up with. It frustrated him because their photos showed so little - just butts in frilly panties and stockings and pantyhose. Nothing as elaborate as the sissy he had made himself into! So he lay back on the bed and caressed his man breasts with his left hand while reaching down inside the black panties to grasp his hardened dick and stroke, stroke some more and curl his toes inside those white shoes until he shot sperm inside the panties as he groaned in ecstasy - and, moments later, fantasized fruitlessly about being with another man, either as his his sissy or as another sissy to fondle.

Mark peeled off his panties and bra and garter belt, taking care to leave the stockings attached. He slipped his feet out of the shoes and placed everything back in their bags before stuffing them back in the recess of his closet and pushing his sweaters into place where his wife would not see them.

Just for the hell of it he looked at his Craigslist email one more time and wouldn't you know it, two men had answered his posting about wanting quick sex that night.

But now it was 11:30 p.m. and he had to go to work in the morning. He answered the men and said he hoped they could get together in the next day or two. He didn't want to spend four nights doing nothing more than dressing up; hell, he could do that while his wife was out shopping.

Mark was anxious. Could he make anything happen over the next four nights? Please, you men on Craigslist, he thought to himself, see what I want, see what I need. If you want I'll dress up for you. I'm good at it and you'll like it.