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“He’s obsessed with boobs,” complained Maria, a new recruit to Mistress Jennifer’s cadre of dominant feminizers of hapless men. “My husband Bob just stares at any woman with a full figure–the fuller the better.”

It was easy to see why this disturbed her. Maria, though extremely attractive, was a petite, small-boned woman who was far from buxom. I was privy to this conversation, along with Teasing Tammy, because Jennifer, Maria, and Tammy’s sister and dominatrix, Susan, intended to use us to bring the unsuspecting Bob into a trap–a trap that would deprive him of his manliness forever, it seemed.

Tammy, though only 16, had been designed by Susan and Jennifer as the ultimate cock-tease, with full 35 C breasts. Although my own alternate persona, Sissy Dani, was generally less generously endowed, for this adventure I was also padded out to Playmate-like dimensions.

We were sent out to meet Bob at one of his favorite hangouts, a bar that specialized in attracting men who “appreciated” bosomy types. I was dressed for “bear”–a skin-tight white satin cocktail dress that played up my bogus breasts with a very short skirt, five-inch white satin heels, and dramatic make-up. Tammy had also been dressed to look older: She wore a black leather outfit, also extremely tight and short, with six-inch heels and equally dramatic make-up.

Our instructions (enforced by the post-hypnotic suggestions that created our submissive personalities) were to approach Bob, get him to buy us drinks, and then get him back to Jennifer’s house for his own transformation.

Within minutes after we arrived, I spotted Bob at the bar. “Well, hello there,” I cooed as I approached him, playing up my charms as much as I could.

“Hello yourself, little lady,” Bob replied, smiling. He looked me up and down, pausing noticeably (as expected) at my bust line. “And who’s this little heartbreaker?” he asked, as Tammy sidled up to his other side.

“That’s my sister, Tammy,” I replied. “I’m Dani.”

He put his arms around our waists, in the process letting his hands graze our “boobs.” I suggested he buy us a round of drinks. He made the order, and I told him and Tammy to find a quiet table and I would bring the drinks when they were ready. Bob readily agreed, seeing a chance, I suppose, to make a little time with the enticing Tammy while alone.

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It was a hot June day. The kind of day that made you feel that you were swimming in the air rather than breathing it. I was sitting in front of the fan trying to stay cool. I was completely naked. I looked down at my body examining the source of my greatest shame. I have an o.k. male body except for the size of my chest.

From the time I was 10 years old I had always been embarrassed by my chest. I remember how free I had once felt being able to run around at the pool with my shirt off, no more. Where a perfectly flat chest had been as a little boy now I had developed larger breasts than some women I knew. I found it hard to buy clothes that fit because of them. I always have to get a large chest size even though the neck and waist is always much too large.

I remember the day at age 13 when it finally hit me that I was different. I was playing happily in the local pool with some friends. I was oblivious to anyone’s looking at me, I had convinced myself that I was too self conscious. It was then that a 16 year old girl called me over to her and said, “Hey Mickey, why don’t you buy a bra!”, I ran back into the pool–crushed. I felt like I had been hit by a cannon ball. I thought to myself, “I wish I were a girl, I would be accepted, even admired for my chest, my breasts, my boobs… if I were a girl.” I stopped going to the pool. Even now some 20 years later I can still feel the pain of that day. I started to sob softly as I remembered it. It was only in private that I felt comfortable with my shirt off and my large breasts exposed. I wonder what they would look like in a bra? Or wearing a dress that was designed with a full cut top and a narrow waist? I wonder what it would be like to get completely dressed as a woman and go out on the town wearing a bra and a dress, and jewelry and having long silky sensual hair? I had never shared my fantasy with anyone, although the thought of it felt thrilling.

As the fan continued to whir, I was awakened from my daydream by the doorbell ranging, I wiped my tear streaked face with a towel and slipped on my shorts. When I pulled open the door a friend of mine, Wendy, bounced in full of excitement and life. Wendy had just been shopping and thought that I could use some company. She said that her apartment was full of the day’s purchases and she wanted to model everything for me. Since her hair was now cut very short she said had even bought a long wig for a more soft feminine appearance on special occasions. But even with her short hair there was no doubt that Wendy was all woman, her curvaceous body was the envy of every woman and the lust of every man who saw her. She had an athletic body that told you she worked out, but she didn’t allow herself to become all skin and bones, you could see her womanly figure tugging at her bra, and her full hips filling her skirt. Even at age 35 she looked like a fresh yet sensual teenager.

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When this story began, you may remember, I slipped Wanda’s panties and little bra from her basement laundry shoot, took them upstairs to my room one afternoon after school, thinking I was all alone in the two-family house we shared. After I put them on, masturbated, sniffed, and rubbed them all over myself (I was careful not to cum on them, but into my hand, which I wiped carefully with tissues as well); I returned them to her laundry shoot when I started to do my family’s wash for my mother, who had left instructions in a note. While I was in the basement, Wanda came down from her first-floor apartment, aroused me, and led me upstairs to my room again, for my virgin fucking and sucking. I had little reason thereafter to put her panties on, fucking and eating her delicious cunt was far more exciting that masturbating with nylon panties on. I loved cunt-licking far more than anything else sexual I had ever even dreamed about. Now you’re about to read about the second adventure with Wanda and her bisexual husband, Wayne.

The following Saturday night, after a boring, sexless week of impatient waiting, Wayne and Wanda had invited me downstairs for more sex play with them, beginning again at 8:30. My friend Richard agreed to cover for me again, if my parents called, and I had given him Wayne and Wanda’s phone number to alert me to call home or to come home. (I was lucky enough to go until 11:30 again with no call, so the second Saturday night orgy was uninterrupted and wonderful.)

When I knocked on their door at precisely 8:30, two, not one, sexy women greeted me: Wanda, the delicate, and a stranger with big tits, which a jersey top could hardly contain. I wanted immediately to release those jugs from her blouse even before Wanda told me that she was Wilma, her sister-in-law. It was dark in the living room, and again Wanda led me down the hallway to their back bedroom. In the darkened front part of the apartment, however, Wilma grabbed me in her strong big arms, pressed me to her voluptuous chest and french kissed me with the largest, searching tongue that ever entered my mouth. She turned me on good; and I had already come downstairs with an erection. I reached up for her mammoth mammaries, but she forced my hand away from them casually. I accepted that and figured that I could wait until she took them out to show me and to have me suck them later.

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When I walked into the bar, I didn’t notice her at first. I sat in a booth in a dark corner and ordered a drink from the waitress.

The waitress returned with my drink, and when I went to pay her for it, she said it had already been taken care of by the blonde at the end of the bar. I looked, and there was Sandy, sitting on a stool at the end of the bar. God, she was gorgeous! Wearing a white blouse, short black skirt, and black fishnet stockings, she sat with her legs crossed, and I could see far up her skirt. She was, without a doubt, the best looking woman in the place.

Sandy smiled at me, and, as she walked over to my table, I couldn’t help but notice her nipples, erect against the soft white silk of her low cut blouse, and the slow swaying of her breasts. She stood in front of me and asked if she could sit with me. “Sure”, I said, and she slid into the booth with me.

She told me that she was a receptionist in the hotel, and that she had just gotten off work a few minutes before. She said I looked like the kind of man she’d like to spend some time with, as she traced patterns on the inside of my thigh with her long nails. As she stroked my leg, her firm, warm breast pressed against my arm with urgency.

Sandy looked me in the eyes, and said she had a room upstairs and she’d like to take me there. She stood, took me by the hand, and led me out of the bar to the elevator. Arm in arm, the warmth of her body and the scent of her perfume were really getting to me! My cock was straining against the front of my pants, my balls tight and full.

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To Miss Stephanie,

It was almost time for Stephanie to get home and Alicia was getting warm with excitement at the thought. She was finishing the vacuuming, the last of the housework that she had told her to do that day. Nothing thrilled her more than playing servant to the tall, imperious girl she had married. She was so beautiful and she loved her so much – that kneeling in submission before her was the supreme pleasure in her life. She had a hard-on in her tight panties, beneath the frilly white apron that covered them, truly a slave of love to that girl.

She heard the front door open and a tingle of titillation went through her. Then she stepped into the living room : a gorgeous creature with long dark hair. She stood with hands on hips, watching her finish her tasks, clad in the white silk blouse and neat black skirt she had worn that day to the office where she was a rising young executive. She had a look of disapproval on her face as she stepped across the freshly vacuumed carpet and dropped into an easy-chair.

“I’m tired, Alicia,” she sighed. “it’s been a hard day, one conference after another. And some of my underlings are no better than you. Inefficient. I have to do everything myself.” She nodded, shutting off the vacuum cleaner as she motioned for her to set it aside and come to her. “Remove my shoes,” she snapped, “and then massage my feet.”

“Yes, Mistress,” she said, hurrying over and addressing her in the form she most liked to hear. It thrilled her just to say those words, the submissive words of a love slave, and she was soon on her knees at her feet. (click to read entire story…)