From my bedroom window, I have a view of the opposite neighbor’s bedroom window. I had previously observed that, on occasion, I saw a woman there who, in my estimation, did not belong there. Interestingly, that woman always disappeared into thin air. Typically, the curtains were closed for a period of time, but on one occasion, they were not. Consequently, I observed my neighbor dressed in women’s clothing. Photo from Valentina.

From that moment onward, I became increasingly curious and began observing him more frequently, watching him dress up. Over time, he began leaving the curtains open more often, allowing me to observe the transformation from man to woman. The woman he created was attractive. She wore a blonde wig, face makeup at the dressing table, panties, lingerie, high heels, and provocative clothing, including short skirts and dresses, as well as leather and patent clothing. He utilized prosthetic breasts to augment the upper torso. Following the transformation, she appeared alluring and seductive.

For hours, she traversed the house or the garden. In addition to being curious, I became increasingly aroused by her as I observed her parading around the room and examining herself in the mirror. She then proceeded through the house, and I also observed her in the garden or engaged in activities there. On one occasion, I was so aroused that I experienced an erection and masturbated in response to her appearance. I had resolved to ring the doorbell discreetly, but lacked the courage to do so. I then masturbated on several subsequent occasions.

The car in question was also present in the driveway today, and I had once again taken up a position behind the curtains for a new dress-up, but the curtains across the street remained closed this time. Moments later, I received an app from that neighbor requesting my presence at his residence in an hour for a specific purpose. I was immediately struck by a sense of unease, as I was unsure of the nature of the meeting and the identity of the individual with whom I was expected to interact.

Nevertheless, I proceeded to shower, during which I shaved my genitals. This was a somewhat futile act, as it would have been more prudent to have done so before going out. However, it was better to be prepared than not.
I then rang the bell, and I could hear the tapping of stiletto heels on the floor as a woman approached the door. The stiletto heels indicated that it was her, and I felt my stomach turn with excitement.

The door opened, and I was momentarily immobilized by her appearance. She was dressed in a short black dress with a V-neckline and shoulder straps, black fishnet stockings, and high-heeled pumps. She also wore a necklace, bracelets, and a short blond wig that partially obscured her forehead and eyes. Her makeup was also quite elaborate, with painted lips and nails.
Was Tom surprised? She said in a hoarse voice, stepping aside. “Come in, darling.” I hesitated for a moment but went in anyway. What a transformation she had undergone. Many a woman had not looked so beautiful and aroused.

I followed her into the room and had not yet been able to utter a word. What do you think? Being able to look at me from so close up is better than from behind a curtain, isn’t it? Had she observed me after all? And what, if anything, would be the consequence of this? Would she be aware of my masturbatory activities? Indeed, she had already ascertained my name, which had previously been Fred.

I took a seat on the couch, she came and sat next to me. I detected a somewhat sweet, citrusy odor emanating from her as she placed her arm behind me on the backrest and nestled against me. Her hand slid down my shoulder and neck to my hair. I encouraged her to speak, suggesting that she not be so reserved. I informed her that she had masturbated on me previously, so this was not a new experience for her.

I apologized for my abruptness, stating that it was my first words. At that moment, I turned my head in her direction. She smiled, grabbed the back of my head, and pushed it in her direction, seeking mine with her mouth. With her tongue, she pushed my mouth open and sought mine. I responded, and we began to tongue kiss. Meanwhile, she put one leg over mine and, with her other hand, reached into my crotch, where a bulge had already appeared.

My hand then proceeded to her leg, where I felt the net stockings on my hand. I proceeded to slowly move my hand upwards, until it reached the area underneath her dress, where I felt the edge of her stocking. With a swaying motion, she turned on my lap and slid forward, until she was sitting against my erect penis. We proceeded to kiss once more, and then pressed our lower bodies together.

She then proceeded to remove my polo shirt, before kissing me once more. With her fingers, she then proceeded to search my nipples and pinch them. I emitted a groan, as I am particularly sensitive to nipple stimulation, and reached beneath her dress to grasp her buttocks with my hands. They were exposed, and I massaged them with my hands, becoming increasingly aroused in the meantime. She rose to her feet, opened my pants, and assisted me in removing them. She also assisted me in removing my panties, which caused my erect penis to become more pronounced.

She assumed a kneeling position between my legs and with her mouth sought my glans. I observed as it disappeared into her mouth, I felt the warmth of her lips and mouth on my glans. I was being sucked, but after a few instances of this, I ceased because I did not wish to reach orgasm yet.

We stood up, she took me by the hand into the bedroom. She guided me to the edge of the bed on which I had to sit. She approached me, pulled up her dress, and exposed her partially aroused clitoris, which she then pressed against my mouth. I opened my mouth and, for the first time, engaged in the act of licking a man’s clitoris. I proceeded to suck on it and attempted to insert it as deeply as possible. With her hands, she held my head and guided the rhythm of the act. “You would make an excellent transvestite,” she moaned. “I will dress you in such a manner at some future date.”

A moment later, her lower body stiffened, she came in my mouth. As her clitoris relaxed, she pulled it back and her fluid ran down my lips over my chin. She licked that up and started licking me, so that her moisture returned to my mouth.

Still panting, she took a seat next to me while my erect penis was still in a state of arousal. She said, “Fuck me,” and got on her hands and knees on the bed. I proceeded to pull her dress over her naked and smooth buttocks and rub my fingers over her buttocks in search of her vaginal opening. I then inserted one finger, followed by two, and finally my entire hand. I then grabbed my penis and pushed it against her opening. She eagerly accepted it and I began to penetrate her. She was wonderfully tight, and I pushed my erect penis all the way in. I proceeded to fuck her slowly, withdrawing my penis and then thrusting it deep inside again.

She promptly turned around when I withdrew my penis for a moment and assumed a position with her knees elevated in front of me. I observed the fishnet stockings and high heels, as well as her questioning genitalia, and proceeded to insert my penis. I mounted her, my gaze fixed upon her, and engaged in oral stimulation. The pace of the sexual encounter intensified, and I found myself unable to sustain this level of arousal for an extended period. From my toes, my semen was discharged and I ejaculated within her. She received it, moaning and with her lower body trembling.

This experience was superior to masturbating in a private space, as she later stated when we resumed our conversation on the couch. This approach allowed for mutual gratification. I concurred, noting that this experience was indeed worthwhile and that we continued to meet regularly.