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I am a cross-dresser who has for years enjoyed looking and acting like a woman. Lulu, my wife, started to enjoy this side of me once she discovered how easily she could dominate me. She likes to expose my transvestism to unsuspecting souls.

At first it was something simple like holding panties up to my waist while shopping for lingerie. But it has progressed to her telling me to buy specific items like a pink bra, a red garter belt or a black teddy. She also insists that I tell the sails clerk that the items are for me. I will be severely punished if I don’t comply, so when we go into the lingerie department and asked what we’re looking for, I will answer, “A pink bra. I wear a 36A.” It never fails to raise eyebrows. I love the embarrassment of it all.

My wife loves to embarrass me outdoors too. We will go to a public tennis court with me dressed in a white shirt and shorts with bright pink panties and a bra that will clearly show through underneath. It never fails to provoke stares. I have also gone to the tennis courts wearing a tennis dress with full makeup and a blonde wig. I’m quite convincing when dressed as a girl, so this doesn’t bother my game. But what does bother it is the fact that I’m also wearing tight nipple clamps and have a buttplug in place.

Lulu thinks I should experience womanly feelings and adventures as much as possible. So in bed I must be ready to accept her strap-on dildo and open my mouth so she can feed me my semen when I come. I also make regular visits to a beauty saloon for wig styling and facials.

A real surprise came a few weeks ago. Our tenth anniversary was fast approaching, and we had talked about exchanging vows again. We had arranged to hire a minister in a small chapel and have another couple, our best friends, stand up for us. This would be on a Wednesday night, and we would take off the rest of the week for a second honeymoon.

I should have known nothing is as expected when Lulu is involved.

She called me at work and told me to meet her at a bridal shop later on so we could get fitted. I thought she meant that I would be renting a tux. But when I arrived at the shop she was inside talking to the owner. They gave me a strange smile when I walked in. The owner looked at me and said, “Yes, I have something will fit him perfectly.”

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Third of the “Deb’s Tails” series. There are more in the works; Deb has told me several others, I just need to find the time to write them down.

My wife, Deborah, often tells me “bedtime stories” of her sexual adventures. Some of them I know are true, either because I was there, or because she has corroborative evidence. Some of them, I’m sure, are fictional. Others, I’m just not sure about.

I don’t know about the truth of this one. It sounds like the kind of thing she’d do if she were in the right mood, but since I wasn’t there, I can’t vouch for it.

If you’ve ever heard anything about the New York subways, you probably think you know what they’re like. Noisy, obnoxious, and crowded. Most of the time that’s true, but as any New Yorker will tell you — once you get past his pride in living in the least livable city in the country — that some trains can be practically empty if you pick the right times and routes. Many evenings, around 10 or 11, even the busiest routes start emptying out, and by midnight it’s sometimes possible to have a car to yourself.

In all fairness to New York, though, it does have it’s good points. The Circle Line is one of them. It’s a mini-cruise around Manhattan (it is an island, you know!) Any place that’s got a decent-sized body of water has something similar. Seattle has trips around Puget Sound, New Orleans has riverboats running along the river. The Circle Line cruise is really beautiful at night with the city all lit up, but in the middle of winter, you can — and probably will — freeze your ass off.

Deb and I often have separate social lives — an inevitable reaction to work-related gatherings where people sit around and talk shop. What usually happened in New York was that I’d stay home and play with my techie-toys while she was out partying with her colleagues, or she’d stay home with a book while I was out cheering for the Mets. Naturally, that meant a few solo subway rides for both of us, often at somewhat odd hours.

This is the story of one of those trips as Deb told it to me (albeit, with my title).

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Sarah and he had been best friends ever since they both could remember. Whenever one of them had a problem, the other was always there to help. Over the years, they had become very close, and had developed a trust that few can claim to know. They were a team, and their friendship was a given, never doubted or questioned.

Lately, Sarah had been having problems with her boyfriend, and was coming to him more and more often for help and advice. On more than one occasion, she would be crying uncontrollably. She found solace in his arms, and quite often remained there for hours on end, while he caressed her and made her feel better. Soon, she began to become more and more confused. She felt a great deal for her boyfriend, and yet she looked forward to being with Joel whenever things went wrong, and that confused her. Once, she even went over to Joel’s house, crying about something that never even happened, simply to be held by him.

His arms wrapped around her, and she felt extremely warm and safe. Almost like a big teddy bear in reverse. Her arms wrapped around his torso, and she buried her face within his chest. Her blonde hair fell around her face, so that he could not tell exactly what she was thinking. She felt a warmth elsewhere, a feeling that surprised her, especially since it was related to Joel, her best friend. She grew worried. What should she do? Should she tell him how she felt and risk losing his friendship? What would change between them?

She soon found out. Her boyfriend broke up with her one day, and the ensuing argument they had totally wrecked Sarah. She sped to Joel’s house, where he was studying in his room. Her eyes, streaked red with tears, told Joel everything he needed to know. Sarah took one step into the room, and her legs gave out. She fell, arms pitched forward as she approached the floor. Joel leaped out of his chair and managed to save her from hurting herself. He lowered Sarah’s limp body to the floor, and then picked her up and brought her to the bed.

She lay in the fetal position, crying hysterically. Her hair was once again covering her face, and Joel tried to stroke it away with his fingers. His large hands paradoxically stroked her fine hair, and she felt better immediately, although the pain of what happened still held her in shock. Sarah lifted herself off the bed, and embraced Joel. He ran his hands up and down her back, saying soothing words to her, hoping that she would feel better soon.

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It had been months since I had seen him. Three months to be exact, three months of loneliness and frustration of the emotional and sexual kind. The intensely sexual kind. Three months of becoming literally a mistress of the art of masturbation and self-pleasuring. Three months of experience which I couldn’t wait to share with Brian.

These were the thoughts that filtered through the sleepiness of my jet-lagged brain as I stared out the tiny fiberglass window of the plane. Not that there was anything to see but the fluffy whiteness of clouds, so there was no view to distract me from my contemplation. And considering the reunion soon to be at hand, I could think of little else but finally ending three months worth of grueling celibacy.

I checked my watch again. Still an hour and a half remaining in the flight. With a sigh I lowered the window shade and nestled my head against the pillow I had stuffed between the seat and the wall of the airplane. My gritty eyelids inexorably lowered, and I dozed…

He stroked my face and gazed into my eyes as I squirmed underneath him. I gazed back earnestly, all of the need and desire mirrored blatantly there for him to see. But still he teased me. Lifting his hips, he probed my pussy with just his cock head, and in my sensitized condition, could almost feel the slit slide like a custom-made groove over my clit. I arched against him further, seeking to suck him inside of me, needing the penetration so badly I thought I would die.

Although I knew he wanted it almost as badly as I did, he still withheld. “Just a second,” he said, “Need to make sure you’re wet enough.” Then his mouth was on mine, his tongue plunging into my mouth aggressively. My eyes were closed, my head swam, but still I could feel his hand snake down between our two sweating bodies, inch into my damp muff, and slide a finger slowly over my clit and down between the cleft of my slick pussy lips. He pushed his finger inside of me, up to his bottom knuckle, and wiggled it around, testing the waters, as his knuckles continued to grind into my hot mound.

“Oh God…” I moaned shakily, “Please…” His hand left my soaking cunt, and slithered up between our torsos, leaving a slimy trail up my abdomen. He stopped to cup one heavy breast, and roughly pinched my nipple. I gasped.

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I hated this feeling. I can can tell exactly where he is standing: over to the side and back a bit. Around the corner of the bar and moving into the hallway. To the bathrooms? Sigh. I am feeling, well, heh, warmed up.

Mmm. If I take a deep breath [BJ breaths in], I can feel the my top tighten against my breasts. As there is no bra tonight, I can feel my nipples rub across the knit fabric. A thick yarn. Rub, rub. My legs too; movement, or squeezing is good. There is that slippery sensation and a bit of dampness on my panties. Arrgh!

What would he be like? I’d love to run my hands through his hair; to feel his hair tickling my fingers. To trace a finger down his chest. What would the hair be like on his legs? Soft and fuzzy like some forest animal? Or strong, tickling my hands as they rubbed his inner thighs? To kiss his neck. He has a beautiful neck. I love to kiss necks; a sloppy sucking kind of a kiss. His ears too. Then to move down to his chest. Maybe nibble a nipple? Wonder what he likes. Across his stomach, which I imagine as a washboard. And then, oh! I should stop thinking like this! Dam it, I’m married!

I open my eyes. Hey — where did Jamie go? Oh, there out slithering with that guy she met on the dance floor. They look like they are having fun. If anything Jamie says is true, boy is he in for a treat tonight! Wish someone would do that sort of thing to me!

Wait. Here he comes again. I can feel that tugging in between my legs. I try to squeeze it way, but it is still there. And stronger. It must be really wet. Mmmm. Oh! He’s coming closer. Checking me out. Ah yes, the usual male scan. Rests a while on my breasts — I push them out and feel my sweater rub across my nipples. Wonder if he saw the expression on my face. Moves down to my legs. I’m wearing a short mini-skirt so he should get an eyeful.

Yikes! Eye contact. I’m locked. I can feel a flood of heat into my face. Good thing the strobe lights, etc. don’t show anything. He looks around at the dance floor. At Jamie. Why did he do that? Back at me. Oh my! He’s coming over. He’s asking me to dance!

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