Searching for throbbing helmets to polish :P

Man in Ipswich, East Midlands, UK

Joined: over a year ago
Last on: 16 hours ago

This is a true story :)

In recent years, I've personally explored the realm of buttplugs, dildos, and prostate stimulation. I found pleasure in these activities, occasionally pushing my boundaries by experimenting with larger dildos to gauge my comfort level. However, I always maintained control over these experiences as I was the one guiding the intensity, speed, and depth of penetration.

Craving a different experience, I started searching online for a unique encounter. While the idea of a man engaging with me didn't particularly arouse me, I knew there were alluring transgender women out there, and I set out to find one in close proximity.

One evening, as I browsed the internet, I came across Victoria, who appeared to be the perfect match. She exuded beauty, had an attractive physique, and boasted a generously sized member. Without hesitation, I dialed her number, and our conversation began. Her English was sufficient for communication, and I straightforwardly expressed my desire for her to pleasure me with her well-endowed member. Over the phone, she sounded enthusiastic and eager to oblige, reassuring me with affectionate phrases like "yes, baby, okay, baby, anything for you, baby. Come now."

I might admit that my own excitement might have colored my perception, as I felt like I'd hit the jackpot. Victoria was just a 15-minute drive away, and she provided me with her address. I set off in my car to meet her.

The area was bustling, with various shops and eateries, but I was fortunate that my rendezvous with Victoria was scheduled for 9:00 pm, offering the cover of darkness. The street was well-lit, and parking was easy. I informed her of my arrival via message, and she promptly responded with her apartment number.

As I made my way to the door, a mix of curiosity and nerves surged within me. I was uncertain about what to expect – perhaps a deceptive portrayal or a significant age difference. The unknown kept me on edge. Upon knocking on the door, I waited briefly.

The door opened, revealing a staircase leading up to her apartment, and Victoria was concealed behind it. Stepping inside, I greeted her nervously, my gaze averted. As I began ascending the stairs, she suddenly stopped me, saying, "Hey, wait a minute." I turned back to find her standing there in alluring black lingerie, complete with a bra, thigh-high stockings, and a garter belt, without any panties. It was her, just as her pictures had portrayed her. I was taken aback by her height, as she stood at nearly 5 feet 11 inches, a significant contrast to my 5 feet 7 inches.

Victoria pointed to her flaccid yet impressively well-endowed member, instructing me to greet it with a kiss. I obliged, bending down to kiss her penis. She then led the way upstairs, and I followed, admiring her figure.

Upon entering the bedroom, dimly lit with background music creating a pleasant ambiance, I handed over the agreed-upon payment of £150 for an hour. Victoria inquired if I needed a shower, and although I didn't, I took one for good measure. The bathroom was clean and well-stocked with towels. Afterward, I rushed back to the bedroom, with only a towel wrapped around me, and there she stood, still dressed in her enticing black lingerie. I was in awe.

Overwhelmed by nerves, I sensed that Victoria could read my unease. She took the lead, gently kissing me as she removed the towel from my waist. She guided my hands, one to her breasts and the other to her penis.

Touching another person's real penis felt uniquely strange, as those who've experienced it can attest. Her flaccid member, although not fully erect, was undeniably substantial. I began to second-guess my decision to let her penetrate me without any warm-up. Typically, I started with smaller butt plugs, but she would be thrusting that massive weapon of hers inside me, a thought that left me increasingly apprehensive.

After some kissing, she turned and began to grind her buttocks against my penis, making me progressively harder. Her buttocks were firm, not as soft as a natural derrière, but still pleasing. After this sensuous buildup, she positioned herself in the doggy style, offering a full view of her anus and dangling penis and testicles. Doing something entirely new to me, I began rimming her, sliding my tongue deep into her anus. She clearly enjoyed it, as she responded with delight each time I paused to catch my breath, her penis growing heavier with each breath, and the sheer size of it made it hang lower and lower.

She turned to face me and sat on the bed. Her penis, slightly curved, stood fully erect. I wanted to take it in my mouth but quickly realized my mouth was too small to accommodate it entirely. I could only manage to fit the head into my mouth. I couldn't emphasize enough how colossal her member was. At this point, I realized I may have bitten off more than I could chew – literally. Though I had practiced with my own dildos and handled them comfortably, her penis seemed overwhelmingly larger. I grew more nervous, knowing that her impending penetration was imminent.

After some stroking and licking of her penis and testicles, she instructed me to lie on the bed. I complied, and she began stroking my penis and playing with my testicles and anus. She then reached for a condom, leaving me to wonder whether it was for me or for her. She unwrapped it and proceeded to roll it onto her own penis. I watched with anticipation as she lifted my legs, positioned herself with my legs against her body, and generously lubricated her penis.

She began to slap her substantial member against mine, highlighting the dramatic difference in size. As she repositioned herself to attempt penetration, she reassured me to relax and promised to go slow. Despite my attempts to remain calm, I couldn't help but brace for the initial discomfort of her entry. She began pushing her head inside, and I felt every inch of it – a sensation I could not ignore. I asked her to stop, and she withdrew immediately, assuring me it was okay and that she would try again, this time with more care. She reapplied lube to my anus and her penis and made a second attempt. Slowly and patiently, she pushed her head inside, and this time, the initial pain was less sharp. I could sense my opening beginning to stretch. She withdrew and then pushed deeper with each motion, gradually filling me up. I had never experienced anything of this size penetrating my anus, and it was stretching my limits both in girth and length. She continued to thrust, increasing in speed. My body started moving involuntarily on the bed, and I was getting a taste of what it meant to be helplessly taken. She leaned over to kiss me while still thrusting, and I struggled to breathe as I kissed her.

After several minutes, she instructed me to get up and assume the doggy style position. In my mind, I wanted to continue feeling dominated, so I arched my back as best as I could, offering my rear end for her pleasure. More lubrication was applied as she slid in effortlessly. She held onto my hips, thrusting vigorously, and I found my arms splayed out to my sides, with only my face pressed against the pillow preventing me from being pushed off the edge of the bed. I was completely submissive to her and her well-endowed penis. She continued to penetrate me forcefully for several minutes, a sensation unlike anything I had ever felt before.

Eventually, she slowed down, almost coming to a halt, but with her penis still inside me. At this point, I began to push back against her, moving my body in rhythm with her thrusts – it was my first time attempting this. She finally pulled out and removed the condom, instructing me to suck her penis again, which I eagerly agreed to. Using my hands and mouth, I did my best, but her member was simply too large for my mouth to accommodate fully. I focused on her head and length, giving it plenty of attention.

Approaching the one-hour mark, she donned another condom and told me to lie down on the bed. After lubricating her penis once more, she eased her way back in, this time not only thrusting into my anus but also stimulating my penis with her hand. After a few minutes of intense thrusting, I finally climaxed, ejaculating everywhere, including onto my own face and the pillow beside me.

Gradually, she reduced the intensity of her thrusts and eventually pulled out. She provided me with wet wipes and tissues to clean up, while she took a quick shower.

With my sense of time somewhat clouded, I began dressing. Victoria returned and asked how the experience had been. I was still in a daze at this point, my legs trembling uncontrollably, and feeling thoroughly drained. I asked if she wanted me to pleasure her again, even though I was fully dressed. She seemed surprised but agreed, as she had not reached climax yet. She sat on the edge of the bed, and I resumed licking and sucking on her penis. It seemed like she was enjoying it, but I suspected I might have exceeded my allotted time. She most likely had another client waiting outside. She reassured me that it was okay and guided me to stand up. I knew it was time to leave.

We both descended the stairs, and she saw me to the door. Before opening it, she requested that I bend down and bid her penis goodnight – a thoughtful touch. I left her apartment and made my way back to my car. A few people were still on the street, waiting for food deliveries, but nothing that would raise any suspicions.

For my first encounter with a transgender woman, I would rate the experience 10 out of 10. It exceeded my expectations, and she indeed matched the woman in the pictures. It was a disappointment that she didn't reach climax, but I wouldn't let that lower my rating. Would I return? Absolutely. I occasionally look out for her, but unfortunately, I haven't seen her in the Ipswich area or its vicinity since.

Matt

35 years old, Bi-curious

5'6" 168cm
Average
Non smoker
Don't drink
No tattoos
No piercings
Size: Average
Role: Oral
Caucasian (white)