My Journey pt 1: Losing my anal cherry and the mix

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My Journey pt 1: Losing my anal cherry and the mix
So I’ve been putting off writing about my first official anal experience as my thoughts about it still remain unsure, whether it was 100% consensual or not. However, whichever way I look at it at the end I did go through one hell of a “slut” period.

Here is the breakdown:

So to skip some boring details but provide some background.

The gurl that ended up taking my anal cherry was, at the time my ex gf, who just so happened to be a ts prostitute (something I wasn’t aware of until about a week or two into our relationship but was ok with it. She wasn’t a street walker but more a call girl and she was officially my 2nd gf to date at this time and we had met in a gay bar. At the time i considered myself straight and wasn’t aware she was a ts until we started getting really close in the booth and we naturally “clicked”.

With her, I had the privilege of having a lot of “firsts”.
1st ts experience
1st giving & receiving anal
1st giving a bj
1st receiving a facial
1st swallowing

I think that covers all of em. Of this list receiving anal penetration from a real cock came as one of the last things.

Most of the time we had sex usually consisted of very sensual and intimate sex, of course with the occasional rough hard sex. Part of it was due to our feelings towards each other but the fact she was a prostitute was a large contributing factor. Especially, the nights she had “dates”, she loved to cuddle after she got home and took a shower, which usually ended up with us getting hot and heavy under the sheets. But bursa escort bayan as a part of her occupation she was always paid to do whatever her clients wanted which could be hard fast sex. So as her bf at the time i felt it was my job to make her feel loved hence why almost 90% of the times she was on a “date”, I’d top her night off with nice slow sensual love making. OF course during her times of heat, I’d pound the living crap outta her since that’s how she liked it but also was the only way to satisfy her at those times.

Well, the night I lost my cherry was no different than any other time she was out on a “date” but something didn’t quite fit. Even after a shower and cuddling/some foreplay, it seemed like she wasn’t able to relax. Eventually, I thought her mood changed as she started to become more dominate, very much more than usual even during her horny periods. I went with it, figuring it might help her mellow out.

Well, after a good period of time sucking, kissing and fondling each other, she stood behind me stroking my cock, which usually meant she was ready. She then asked me to reach over the bed to grab the lube. So I did and handed it to her. Next thing I know, she just pushes me face down into the bed then I feel lube being drizzled between my cheeks. Before I realized what was happening, she had already popped her head into my virgin hole. In utter shock, I naturally clinched down on her. Her reaction to this was grabbing my shoulders and did a push/pull action, burying her cock balls deep in me in one thrust.

For a ts escort bursa her size, 5’9 no more than 140lbs, she was well equipped. 7.5-8 in cock that was 2-2.5 inches thick. A lot bigger than any other plug I ever used for sure.

She essentially knocked the wind out of me and my body’s reaction was to clinch even harder. She then took this as a signal to pound my once virgin ass for a solid 30 mins. Of which, she had me utterly speechless for a good 5-7 mins as I attempted to adjust to her size. Then, somewhere after the 10 min marker a switch flipped in my head and from what I remember/she said, I started pushing back on her in total ecstasy. The longer she fucked me the more frustrated she became and the harder she’d fuck me. Part of the reason she fucked me for so hard and long was the fact that her hormones made it very difficult for her to cum. Eventually, she reached a point where she just pulled out and held my head to her cock while she jerked her and plastered my face with her cum, leaving me on the bed a sweaty mess.

Immediately after, she cleaned up and left the apartment. I remained on the bed for about 20 mins in utter shock from what just transpired. Covered in cum, barely able to sit, ass gaped wide and bleeding, I cleaned up as best I could and headed to my place. Given the circumstances, I was fine but the next morning/day, the events of the previous night kept replaying in my head. My feelings were doing a roller coaster and I couldn’t figure them out. Basically, the betrayal of what transpired but the fact I did enjoy it. About bursa escort a week past where I didn’t make any attempts to contact her or return calls.

She knew something was wrong and eventually I agreed to talk. When we talked, I expressed ALL of the feelings I felt, initially betrayal of being forcefully taken but also the fact I began to enjoy it, and she also opened up about why she had snapped and taken me forcefully. From her explanation, one of her regulars clients, who she used to have intimate bareback sessions with prior to us dating, had an argument about her services. He basically wanted the usual intimate/bareback session they normally had but she refused because of our relationship. He then pinned her to the bed, forcefully kissing, fucking and breeding her, then threw the money he owned her on her, while saying “a whore is a whore, here is your money whore”. While wiping tears from her eyes, she then mumbled “what really bothered me was the fact that I liked it”. She then followed by saying “this wasn’t the first time I was forcefully taken and liked it” and told me about a close friend who regularly used and m*****ed her when she was younger. She always resisted his advances, to make it seem like she wasn’t gay (as she identified as male then, she wasn’t aware at that age she was a transgender). However, something she never told anyone before was that she secretly enjoyed it and often masturbated to the thoughts of what he’d do to her next time.

Funny, thing is that when she told me this, I actually started getting turned on and hard. This opened up a whole new aspect to our relationship and my sexuality.

More to cum with part 2 🙂

Anyone is more than welcome to provide their comments or thoughts on this.

FYI, I still do occasionally ponder about this to this day.

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