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The agreement was that Hope would meet John on the ground level of the apartment building at the elevator bank. They would rise together in the elevator to Hope and Tom’s apartment on the eighth floor. The agreement was that for Hope and Tom’s 10th anniversary, Hope would grant Tom’s ultimate wish–to watch another man fuck Hope while Tom watched.

Hope nervously paced the ground floor, waiting for John, wondering if she would regret her agreement with Tom. She loved Tom and very much wanted to please him, but she had never shared her body with another since their wedding and worried about the consequences for their marriage.

Yet, after much discussion and mutual reassurances, both Hope and Tom had begun to feel an unequaled sense of anticipation…of excitement. Now they had only to hope the careful selection of John as a partner would not be regretted.

Hope turned as she heard slow, solid footsteps approach behind her. She looked up into John’s smiling face, his eyes dancing with light.

“You sure you want this?” he said as he brushed Hope’s hair from her face.

“An agreement is an agreement,” Hope smiled as she pressed the elevator signal “UP.”

Hope’s heartbeat began to quicken as she pressed the elevator button for the eighth floor. She quickly wiped away a narrow line of sweat upon her upper lip and hoped John would not notice as the elevator began to rise.

John smiled and Hope felt drawn to the lively crinkles around his eyes as he did so. John was well-built, at least eight inches taller than Hope and she wondered if he liked short women. She asked him his feelings and John responded, “You’re not short. You’re petite.” They both laughed.

John smiled again and reached across the elevator to pull her closer to him. His hands caressed her breasts and suddenly his hands grasped her narrow waist, lifting her and bracing her against the elevator wall as he pressed his body against her. As John’s warm mouth covered her lips, his tongue darting back and forth, Hope felt his hardened dick shove into her crotch. She gasped for breath as the elevator door opened and John lowered her to the floor.

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Their eyes had met at the turnstile….his fare ticket had been returned with a “See Attendant” notice, and his blush was very noticeable against his blonde beard. Rachael smiled sympathetically as he moved aside and let her through.

Sexy eyes she thought to herself as she walked to the escalator descending to the train platform. Hearing the train doors open, she ran quickly down the slowly moving stairway and arrived just in time to see the doors closing and the train pulling away. “Nutz!” she mumbled under her breath, and moved to her accustomed queue position, where she opened her novel.

The ill-fated mad dash to the train platform had made her warm and she removed her long coat, dropping her book in the process. As she bent over to pick it up, her rear end bumped against the person in back of her, and she swiftly straightened, turning to apologize. Now it was her turn to blush as she saw that same blonde beard and sexy eyes she had encountered upstairs at the turnstile. She had noticed him many times before, and had imagined he had watched her a few times as well, although she didn’t think it was true.

She averted her eyes quickly, not knowing what his thoughts were, but she couldn’t restrain her own. She tried to go back to her book, but couldn’t concentrate. The stranger had stepped forward to the side to look down the tunnel for an oncoming train, and she could see the slight bulge in his suit pants in spite of the jacket he held over his arm. He stepped back in place behind her, and she went back to her story.

Soon, she felt something push gently up against her ass, which felt much like a briefcase. He must have made a mistake, she thought, and mentally forgave him. Shifting from one foot to the other, she couldn’t help fantasizing about this stranger behind her. She had noticed he was about her age, of average height and weight; the kind of teddy bear she would love to hold and suckle. His face was that average-guy good looking, with strong cheekbones (what she could see beneath his beard), and smiling blue eyes.

Well, what am I doing day-dreaming about him” she asked herself. After all, he probably wouldn’t even LOOK at me. She unobtrusively tugged at her slightly snug blouse, smoothing it over her breasts, and rounded hips.

She had been uncomfortable all day, noticing how this blouse accentuated her large breasts, and how the new brassier she was wearing held them up and allowed them to bounce MUCH too much when she walked.

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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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