A Crossdresser Takes the Plunge

Let’s take the case of a crossdresser named Lin, not Linda, not Lyn or Lynn but Lin. She has gone through all the usual steps in life — trying on the panties, adding a bra, enjoyment leading to sexual arousal, ejaculation and purging only to return to it later. Any of these steps could be an ‘end of the line’ for most males. However, for Lin, as with almost all crossdressers, next comes trying on more femme clothing and starting to acquire a wardrobe, more arousal, more purging, perhaps an episode of getting caught.

Yes, most of us have ‘been there; done that’ eh? Later comes the makeup and eventually Lin was able to find herself a wig. Heaven! It was getting harder to store all her stuff at home so she invested in a Public Storage locker. She liked the way she looked. Lin got a video camera and started recording herself, standing, sitting, walking across the room, usually a hotel room. She would even take short trips down the hotel hallway or out into the parking lot, all recorded on film for her and only her to see.

The strange thing was that the more Lin practiced her art and the better she felt she became at expressing her femme self the less desire she felt for sexual release. It was becoming more important to Lin to be all that she could be as a feminine image rather than sacrifice the feeling to a short-term sexual urge. The arousal was still there but satisfaction could wait. Lin had other things she wanted to do.

Other things? Yes, Lin liked the way she looked but she could not help wondering how others would see her. Soon trips down the hotel hall were replaced by trips to the mall. Stops at the vending machine were replaced by visits to a city’s trans-friendly night club.

How did that go? Lin noticed that she did get more than her fair share of second looks. However, no one seemed overly obnoxious toward her and the store clerks were very friendly and accommodating when she wanted to try on dresses and other clothing. She developed the hypothesis that it was more important for her to be ‘presentable’ as opposed to ‘passable’.

Lin was by nature a gregarious and friendly person. Friends told her male self that he should be in politics. However, he declined feeling that it would be a tremendous personal disaster if he were to be outed. But HIS friendliness carried over into Lin’s personality. Women liked Lin and they shared advice. “Be expected to be noticed,” said one, “after all you are near six feet tall.”

“Stay away from really high heels. You are tall enough already.”

“Wear large print dresses and blouses,” said another.

Even her wife chipped in some advice. “You really should keep those nose and ear hairs clipped,” she would say.

The advice kept coming. “You have lovely blue eyes so stay away from blue eyeshadow.” That one threw Lin for a loop and had her running to the mall restroom to cleanse some color off of her eyelids.

Yes, Lin had become comfortable enough going out that she used the ladies’ facilities. Even if it was just for a day, a weekend at a time; a week at most Lin had reached the stage of blending into the typical single girl’s lifestyle. She had other t-gal friends who she met from time to time. She liked going shopping. Her storage locker had grown several times. She liked going to galleries and museums and with friends to movies and concerts.

She had everything a single girl could want except she did not have a male friend, a boyfriend, a lover. At one point Lin must have said to herself, ‘I like the way I look. My t-friends say nice things but what about men? I do get hit on occasionally at drag bars but I haven’t been interested. Maybe I should give it a try. Am I sexy enough to turn on a man? Can I really consider myself a woman if I have not excited a man to the point of his climax?”

Now you may think that was a very bizarre thought process. Do we really need sex to feel fulfilled, to feel validated? I will leave that to you to judge for yourself. This is Lin’s story.

It seems Lin is a bit of an obsessive-compulsive character. When she gets an idea in her head it is not long before she acts on it. So it was with her idea to test if she could arouse a male lover. This was not a small step for her. She had always considered herself heterosexual. Her male ego had two ex-wives and three children to support that idea.

Her planning was extensive. She would go to a city and to a drag bar that she knew attracted a lot of admirers. She had seen other t-gal customers pairing up with the men. She knew what was going on. She knew she had to prepare. She bought a ‘butt plug’ from the local adult store. She practiced giving blow jobs to bananas but that was tough. She loved the taste of bananas. She knew she would not be allowed to bite the head of a date’s penis. She had heard about the gag reflex and she worked to overcome it.

The butt plug was more difficult. She was very tight down there and she could not seem to relax. Even with a lot of lubricant entry was not easy. Why? She wondered. Thicker stuff comes out; why is it so difficult to get something in? It would not be long before Lin started to discover the answer.

It just happened that Lin’s work had her going to Montreal, Canada for several days. Of course, she would be in male mode for work but she planned to stay over some extra days and nights to enjoy the pleasure her femme identity gave her and to try find a man for her experiment. Back in those days her ‘go to club’ was the Pyramid Club, upstairs above a strip club called Chez Cleopatra. While her normal evening at the club had been Fridays when she could join up with a group of partying crossdressers this time it would be Thursday to Saturday.

That fateful Thursday night Lin arrived at the club early expecting the place to be near deserted. Things usually did not get going in Montreal until almost midnight. The club had a two-drinks-for-the-price of-one policy before 11 p.m. to try to attract an earlier clientele. It usually did not work but this Thursday the club was busy.

Lin was soon to learn that it wasn’t the drinks that brought in the customers that Thursday evening. No, it is probably the same in many cities but Thursdays seem to be the night that many married guys make excuses to be out for the evening. It may be poker or bowling or a work meeting they tell their wives but it is typically a little ‘walk on the wild side’ for these would-be Romeos. Then there are the guys who have been in town for conventions or sales meetings. Their business has basically wrapped up, but their return home is not until the next day. Time for a little wild side action.

At the Pyramid Club the tables were arranged in a U-shape around the stage and dance floor. Lin grabbed a free table against a back wall where on previous visits she noticed was favored by single girls. While she was prepared to wait and listen to the music, it was not long before a waiter appeared with a drink ‘compliments of the monsieur at the end of the bar’. At the Pyramid Club sending you over a drink was code for requesting permission to join you at your table. The waiter added that he was a nice man and he spoke good English. Lin told the server to send him over. This was it; she thought to herself, do or die.

I am not going to go into a lot of details. I have dated a lot of guys at the same Pyramid Club. Some were really nice but rarely would I have been treated as royally as Lin was. First time lucky or did she have that certain ‘je ne sais quoi’ that attracted men like bears to honey?

Lin told me the whole story about how her new friend took her to his hotel room, poured her a drink and retreated to take a shower. He returned with a towel wrapped around his waist. It dropped away as he climbed onto the bed with her.

“But you are not gay. How could you get yourself to go with him?” I asked.

Lin said she was surprised how easy it was to let him kiss her, for her to fondle him, for her to give him oral sex. She had had bigger bananas, she said, but none as hard and later she came to appreciate how nice it was that he had showered and washed himself down there. Lin’s banana practice apparently paid off. She knew how to back off before gagging, how to even incorporate all those tricks that her wives and girlfriends had tried on her. She also knew how to take and swallow his discharge without tasting it.

He must have liked their sex but that did not stop him from expecting her to leave straight way. “All through it I did not feel particularly aroused” she added. “To me he was the subject of an experiment to see if I was sexy enough to turn on a man. In the end he was just another banana.”

“Experiment a success, I assume?”

“Totally,” said Lin. As she left, her ‘date’ did something she did not expect. He handed her three crisp Canadian $100 bills. She guessed that was what he thought was the going price for sex at the Pyramid Club.

“I thought it was more like $30,” I told Lin.

“That was what I found out later,” she said, “but in the meantime the $300 was great incentive to have me coming back for more.

“The next day I found to my relief that the experience had not changed me,” she added. Lin explained that giving oral sex to a man had not made her crave men or crave their penises. It did seem to make her enjoy being able to turn men on. Homosexual? Probably not. I like to consider it being somewhat ‘ego-sexual’. Lin enjoyed the feeling of her own pleasure, no matter how it came.

That was Lin’s first exposure to the world of admirers. She loves them. I love them. In the next while we were to have some great discussions about our admiring friends and what might make them tick. I am looking forward to telling you all about them.

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Tags: crossdressing, featured, sex

Category: crossdressing