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danisharemedy · 1 year

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Nervous But Ready

Transgender erotica

It has been about a year since my divorce was finalized. My ex-wife and I were married for 3 years and had no kids, so the divorce was relatively painless compared to other people we knew. We've always been friendly to each other, but we just didn't love each other like we thought we did when we first were married, and the honeymoon stage had already set in.

We broke up soon after we mutually agreed on a divorce, and I moved into an apartment an hour or so away from her. I refrained from seeing people while we were married, on the advice of my attorney; however, I had a strong desire to meet someone new and move on. I figured I'd meet a girl walking around the block, and then we would laugh like kids before kissing each other.

Before I met my wife, I had very little experience with women. She was only the third woman I had sex with. I wasn't a stud like my older brother and was often thought of as a “nice guy”. When our marriage started to suffer after about 2 years, I started watching more and more. Our sex life was practically non-existent as my wife seemed to show no interest in us. It seemed like every time I asked her about it, she had an excuse of some sort. I think she was seeing someone else, but I'm not entirely sure. She never admitted infidelity to me, so I just didn’t think about it.

Around this time, a friend of mine told me about an acquaintance who had met a transgender woman and dated her for a while. He surprised me because he never seemed like the type to lead such a lifestyle. Although I have always been pro-LGBTIQ, it never crossed my mind to think about transgender people and sex in the same line of thinking, but after I started watching porn, I periodically came across transgender pages on some porn sites. I didn't know at first that I was going to be looking at transgender women, but after hearing my friend's story, I looked and was amazed at how attractive some of them were. For many of them, if I passed them while walking, I would never recognize them and would simply find them very attractive. I think I suffered from internal transphobia, but I had a feeling that soon things would change…

Also, when I started watching porn online, I realized that I was especially interested in watching women giving blowjobs. It struck me that these women willingly allow men to cum in their mouths or on their faces. I came across a video where a girl was wearing a cheerleader costume and had to please an injured football player. She was a little shy at first, but when she started kissing, she started to undress. She then knelt and stroked the black cock in her mouth until the semen descended her throat and onto her face. I thought it was porn and not necessarily reality, but I had a girlfriend in the past who seemed to like this too which made me know that this scene could still be a possibility in my life. Oddly enough, she was my wife's half-sister, but we broke up. once my wife and I met.

This was not the case with my ex-wife as she rarely took me in her mouth and never let me cum in her mouth. To be honest, my wife didn't really like sex other than the vanilla missionary positions. The closest we came to anything kinky was when we blindfolded each other on one occasion.

As I watched more porn, I realized that I am not afraid of cocks and am more interested in what it is like to give a blowjob. I wasn't attracted to men at all, but I was very attracted to some transgender women and their dicks increased that attraction. I started fantasizing about being with a transgender woman while masturbating. I wanted to feel what it was like to hold a cock in my hand and run my hands through my veins while the head was in my mouth.

So, finally, after signing the divorce papers, I decided to explore the possibilities. The lack of interest in men in general made going to a gay bar unpleasant, and I didn't know if there were any transgender bars. So, I decided to search the internet for options. In doing so, I came across several websites offering trans women escort services. I thought it was probably dangerous, but after reading many profiles, I learned that many of them express on their pages how serious they are about preventing sexually transmitted diseases and protecting their partners with the use of frequent testing. But the main thing I liked was that they were willing to keep everything a secret. Most likely for married men or someone like me who was new to the industry.

There is one that really interested me. Her name was Leila. She had long French braids and chocolate brown eyes. She was amazing and reading her online reviews of her wowed me. It was obvious from the reviews and photos that Leila was quite well endowed and could cum, even multiple times in one session. She was also willing to entertain newcomers like me, and she said she was happy to take responsibility and play a dominant role.

I jerked off to Leila reviews several times and every time I wondered if I had the guts to blow someone. It was strange that the reviews themselves were written as erotica. If I had tried to meet someone like Leila, I would have to know a thing or two beforehand. So, I experienced the tasting myself.

First, I felt my pre-cum while I was masturbating. It was salty at first and I felt so guilty that I didn't do it for several days. After a few times, I started liking the taste, but I knew sucking cock would be a very different experience. I finally worked up the courage to try and lick up some of my own cum after I came on my chest. I took my finger, swirled it in a pool of cum and brought it to my mouth. It was ok, but not great. I kept doing it and it eventually became a routine that I grew to love. I fantasized about sucking someone else off while trying myself. Eventually, I decided that for me to experience something closer to reality I would need to cum directly in my mouth. It took a few tries of flipping my legs over my head to aim right and cum in my mouth, and it took a few more tries for me to not be afraid of it. Probably about the sixth time is when I swallowed what was in my mouth and didn't have any gag reflex. My gag reflex wasn't triggered by the taste. The taste wasn't that bad. It was more about getting over a mental block that it is okay to swallow cum.

Eventually, it got to the point where I was ready to see if I could meet Leila. She had a telephone number where you could arrange a meeting. One Sunday afternoon while I was masturbating, I decided to call her, thinking I wouldn't be able to reach her and would have to leave a message from her.

She answered! "Hiii, this is Leila!”

“Um, hi. I saw your adt on the Internet and wanted to know if I could make an appointment."

“Okay, Darling, tell me about yourself. Where are you from and what do you do?” Her voice was very soft and feminine. I really couldn't tell the difference from a female voice.

"My name is Timothy, I'm a local resident, recently single, and I code and build language learning apps."

"I see, so what are you interested in? What are your fantasies?"

"I'm new to this, actually, this is my first time."

"It's okay Darling. So, what are you fantasizing about?

“I have read some of your reviews online and fantasized about what they write. I love that you are fully dominant and exceptionally beautiful.

"Thank you, Darling. I do a lot of things, so it's hard for me to understand what you're talking about. Can you be more specific?"

“Well, I've read some reviews about you liking to be on top, so I like that. I really liked the review where you took the lead and got blown by a guy and you came inside his mouth many times.

"That's interesting. I think I know what you're talking about. Do you want me to set up our date?"

“Yes, I think that would be a great idea!”

“I like being in charge,” she laughed. “Have you ever been with a man or a trans woman?

"No to both, but I've experimented with myself."

"What do you mean?"

"Well, you know, I masturbated and got a taste of myself."

She laughed as if enjoying the conversation. “How many times and do you like it?

“I've done it many times. I've worked on the technique, and I like it. I think about it a lot, especially when I masturbate."

"This is very perverted, Darling," she said with a soft laugh. “I like doing it too. Have you already learned to swallow?

“Mostly, I think.” I started imagining it in my mouth when I answered. “I tried several times to cum in my mouth and sometimes I hit the tongue. I even tried to lick it off my hand."

“Oh, I like it. Did you swallow it or spit it out? I hope you don't mind all the questions. I'm just fascinated by straight people who try it and love it."

"I'm not against the questions. I've never told anyone before, so it's a little embarrassing. I spit at first but now I swallow most of the time”

"This is incredible!" she said enthusiastically. “I hope you like it because I find it intoxicating. So, do you dream of doing what you just described?

"Well, in a way, but I'd like to try it with someone else. Like I would want to feel someone else’s cum in my mouth"

"Interesting. Ok, Darling, what day do you want to meet me? I can meet in a week, starting on Wednesday."

"Thursday or Sunday free?"

"Not for some time. I can meet during the week on Wednesday at 10pm. Or we can reschedule if you need to meet on Thursday or Sunday. Wednesday is best for what you are looking for. How long would you like to come to our meeting?"

"Wednesday is fine. Would you like to do it for a couple of` hours?"

"It looks perfect." She received my e-mail address and said she would send me her home address.

“Excellent. See you then,” she said. “Don't forget the test results. This is written on my website.”

I ended the call. I couldn't believe I had the courage and booked a time with an escort. I was shaking with nervousness and continued my jerking off while looking at photos of Leila. When I was ready to cum, I opened my other hand and tried to cum into my palm. The first few shots hit my laptop screen, then I was able to grab the rest in my hand. "Damn it," I thought. I really didn't want to cum on my laptop. I looked at my hand and thought maybe I'd get a chance to suck Leila. I needed to prepare. I looked at my hand again, moved my face to my hand and licked it hard. I then looked in the mirror at my desk and saw my tongue was lubed up with cum and then I swallowed it. I figured if it would be sweeter or saltier than mine. Not so bad, I thought. I can do it.

The next day, I signed up for an examination at the clinic. Also, to prepare for possible penetration, I bought a few small dildos from a local sex shop and tried shoving one up my ass a few times to get used to having something inside. It took a while, but I finally got it all together over the weekend. I even tried sucking on another dildo to get used to having something like this in my mouth. And just the day before my appointment with Leila, I shaved a little and shaved my genitals. I usually keep my hair short and neat, but I thought a clean-shaven one would be the most attractive.

Wednesday finally arrived. When I got home from work, I showered and got ready. I was shaking and nervous again. At one point, I almost backed out and started making excuses not to go, but again I looked at photos of Leila on the Internet and decided to go. I won't lie, they excited me, but I was still a little nervous. I could just give her a tip and walk away if I wanted to just go back home.

Leila's apartment, or workplace as you might call it, was very nice and felt luxurious. From the outside, you wouldn't have guessed that this is where the escort invites her clients. You would think this would be where a rich family or people of the sort would live. I went to the door and rang the bell. The door opens. Leila stood in front of me in a short black silk dress and high heels. Her blonde hair was tied back, and her wispy bangs barely reached the tips of her eyes. Her lips looked moist and almost natural in color, and there was something shimmery about her face and neck, like tiny sparkles, but not too much. She looked incredibly sexy. Her legs looked very toned and slightly muscular, and her feet were sexy and small with red nails that matched her toenails.

"Hi, I'm Tim. We spoke on Sunday a week ago".

She looked at me. "Wow, you're cute," she said with a big smile. "Come in." She held out her hand and I reached out and took her hand. Her hand was soft and warm.

I entered and saw a small narrow corridor. To the right, just behind the door, was a soft bench. Opposite the bench to my left were hangers on the wall and a small table to the right of the hangers. Above the table is a photograph of Paris. On the table was a jar with the inscription: "Donations are welcome." Opposite the door on the opposite wall hung a large wall mirror, and to the left of the mirror was the entrance to her apartment.

“Sit down, Darling.

"Of course." I sat down and she sat to my right. She grabbed my right hand, put it on her knee and held it.

"How are you feeling? Nervous?

"Yes, a little," I said. I felt shaking.

“You have nothing to worry about. If there's anything you don't like, let me know. You still want our time though, don't you? Or are you not interested?"

“I am still very interested”

I am so very glad to hear that.” she said with a soft laugh and a smile. "I remember you saying you wanted it, so if that changes, let me know."

"Of course!"

“Did you get me the test results I asked for?”

It was folded in my jacket pocket. "Oh yeah, it's right here." I pulled out the form, the results were clear. She looked at them briefly.

"Fine. Thanks. I have to be careful; you know." She folded the paper, reached into my jacket, and slipped it into my pocket, then I felt her fingers and her hand on my chest. She squeezed my left pectoral muscle. "Oh, you're smooth," she said. “I love strong men. Why don't you hang up your coat here and come here in about a minute? I am freshening up now”

She got up and went to the door, then turned to look at me. She gave me a seductive wink before walking away again. Her big ass jiggled with each step and I was mesmerized. She was cute! I couldn't believe how sexy she was in real life. She already looked good to me in the photos and obviously they hadn't been enhanced. Her dress was partially unbuttoned, and I could see her gorgeous cleavage and something black underneath her. The bottom of her dress was just below the crotch, and I noticed how tanned and firm her legs were. Finally, she left my presence through the door.

I got up and figured it was time to cancel if I wanted to. And believe me the thought crossed my mind. But I didn't want to leave this opportunity. I got so far that I had to go all the way. Leila looked great and was well worth checking out. I took off my jacket and hung it on one of the hooks. Then I looked at the donation jar and decided it was better to put the money in the jar now than later. I paid the suggested donation listed on her website and added much more than was asked for. I wasn't worried about the money so if I left early, she still deserved the full amount for taking the risk to meet me. Next to the jar, framed for a photograph, were the previous week's test results. Her name was on it although some of the other information was redacted.

I turned to the mirror and looked at myself. My shirt was buttoned all the way except for the top, and I decided to unbutton one more button to look more casual. Has it been a minute? I waited a little longer and headed for the door. My legs were shaking but I had resolved I would go at least a bit farther.

When I got to the door, she was standing inside and to my right, smiling. She turned to me and stopped in front of me again. She had shed her dress and was wearing a black lace lingerie piece with a plunging neckline that framed her barley-firm breasts. The sides of hers were open, her thongs were wrapped around her back, and her crotch was barely covered tiny panties of the same color. She was still wearing her black high-heeled shoes.

Behind her were the glass doors were open, and in the bedroom, I saw a large double bed with a crisp white sheet. There was an armchair next to the bedroom.

Directly ahead was a small sitting room with a sofa and two double sofas with coffee tables, and to my left was her kitchen.

Leila approached me sexily. The mesh looked very enticing, and her hard, brownish nipples poked through the fabric. I couldn't help but stare.

"Hey, sexy," she said, slowly approaching. I turned to her as she stopped in front of me. “Do you like my dress?”

“Oh yeah, I like it. You're amazing." I was surprised by the question because it sounded unbelievable.

Leila smiles. "Why did you come to me, Timothy?" I hesitated, still stunned by her beauty, and couldn't find her words. "Do you want a big juicy cock?"

"Yes," I said. She leaned forward so that she almost touched me with her body.

“I remember what you said on the phone. You like to taste yourself." She smiled into her eyes and brought her face close to mine. "I think it's so hot," she almost whispered, running her tongue over her lips. "I love the way my cum tastes too."

I felt my cock begin to firm up and was incredibly turned on by how sexy this all was. She grabbed my hand and led me to the center of the room closest to her bedroom. She turned around, unbuttoned my shirt, and put her hands on my chest. "Oh, you're so hot," she purred to me, squeezing the muscles in my chest again. She then she let her fingers slide over my nipples and her stomach. She pricked me with her fingers. "I also like your toned abs." She reached out, pulled my shirt off my shoulders and arms, and tossed it onto the sofa.

“You have a sexy body. I want to lick you”

"Thanks, Darling." She stroked my chest again, then leaned in to kiss me on the lips. I hadn't kissed in a long time, so it was thrilling. She knew she had been drinking red wine.

“You're nervous,” Leila said. "Relax Darling. She kissed me again. Her tongue touched my lips, and I took it into my mouth. She was like any other girl kissing and I started to relax a bit. After a minute or two she stopped kissing me and she slid one of her hands up the front of my pants and squeezed my semi-hard cock in. I immediately released a groan and threw my head back.

"What do we have here?" she asked, looking at me with a smile.

"Uh", I was incredibly slow to react.

“You seem to be a little nervous. What do you want to do with it?” She smiled devilishly, looking into my eyes.

"I want to fuck you."

"Of course. Maybe it's possible," she giggled. "You want to be fucked too, don't you?"

"Yup."

“Good, because I meant to. But I'll like to have my way with you first, Darling." She pulled both of her breasts out the lingerie, grabbed my hands and put them on her. Do you like how they feel?"

"They feel great." I squeezed them gently and realized she liked it.

"Don't worry, you won't hurt me." “Feel them.

I squeezed tighter and ran her thumb over her nipples and they got even harder.

"Mmmm, that's so cute, honey."

She reached out and unbuttoned my pants. "Take them off."

I took my hands off her and took off my shoes and pants. “Socks too,” she said.

I took off my socks and threw them aside. She then massaged my cock through my boxers. “He looks very hungry, Darling. I cannot wait to see it".

“I can't wait to show you,” I laughed. Leila laughed too, but then she returned to a more serious face.

She took my hand, put it on her panties and said, "Touch me." I felt a slight sick in my stomach, but not what I expected. I think I was just nervous.

She knelt down and took off my shorts. My cock was pointed straight at her face. She grabbed it and stroked it several times, then she kissed and nibbled on the head. "Dear God, you are so huge! And I love that you shaved. I can't wait to play it later,” she said with a cheerful expression.

Later, I thought? She stood up and kissed me on the lips again and explored my mouth with her tongue. I used my hands to stroke her bare back and explore her entire body as far as I could go, then she stopped kissing me. She walked over to a chair near her bedroom door, turned to me, and pulled her panties off. Her cock leapt out from under her legs and headed down. Her cock was long and well formed, as I would have expected from photographs of her. She was also completely shaved. She sat down. As I wanted, she had many visible veins and, surprisingly, her dick was bigger than mine.

“Come here Darling” I approached the chair and stood in front of her completely naked.

"Get on your knees and take off my shoes, please." I looked at her feet. They were as sexy as any other girl I've been with. I knelt down and she lifted her foot into my lap. I took it in my hands and found a buckle to undo her straps. I then started to worship her feet sucking the toes. I then moved my tongue down the arch of her foot making sure every inch of her foot was wet. I then put her foot down looking to her for more instruction.

She then used her toes to push my cock and keep it hard. She put her other foot in my lap, and I took off my shoe.

Leila then used both legs to briefly massage my cock and I felt tense. I put her hands under her legs and lightly stroked her calves as she stroked me with her toes.

“You are so beautiful, Darling"

"You are so cute," I said, looking briefly into her eyes. Then I let my gaze travel up her body to her sexy breasts, her flat stomach, and then her cock still dangling between her legs. It was probably 5 inches and still mostly soft. I've never been in front of another member like this before. The closest thing I had to another dick before was a shower in the locker room while in sports, but then I wasn't looking at anyone. I realized I was staring and looked into Leila's eyes.

“Are you ready Darling?”

I nodded affirmatively as I slowly put my head down. This is it. This is what I tasted my own precum for. I started off just by smelling it let its scent fill my nose. It had its own special smell, feminine like my ex-wife, but with more hormones filling the air. I was so nervous, and Leila could tell which is why she started to run her fingers through my hair.

“If this is too much Darling we could stop and just sit down for a while. I’d understand.”

“I am a bit nervous but...”

“But what Darlin-ughh”

She let out a small moan as soon as I kissed it. After I kissed it the second time…

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