My First Experience With A Shemale – Part 1

I was on my knees with my hands holding her butt. The smell of her orifice is something that is still fresh in my nose, even after hours. I inserted my tongue between her butt cheeks. I could feel the hair around her orifice on my lips and my tongue. It tasted a little sour, a little tangy.

But what aroused me was the feeling of her asshole, it’s wrinkled border on my tongue and the hair around it. My mouth was open wide and my tongue incessant. After a little while, her hole started to give in to the pleasure it was receiving.

It was opening up a little to give out a little prolapse that is common for someone who receives anal. In between the wrinkled border of her asshole and the hair was soft and meaty. I now had a hand on my penis as I stroked it. Another splitting her butt as I used my tongue up and down and around her asshole.

It was wet with my saliva. The aroma that was arising from there went straight up my nose, inspiring me to put more effort into what I was doing. After I could feel an orgasm building I left my dick alone. I used both my hands to spread her butt cheeks.

Like a hungry animal, I licked the area with a dedication that I have never shown towards any act throughout my life. I wanted more, my mouth and my nose were between a tight, round, smooth, and firm butt. I could feel her ass cheeks pressing against my face.

I let them go off my hands. My face was now between her ass and I started caressing her thighs to make her feel loved. At the same moment she started thrusting her butt into my face. All this wasn’t met with a cold reaction. I could hear her moan and say ‘yes’ every time my tongue completed a lap around her hole.

In between I will use a finger to penetrate her anus, the tightest thing it ever came across. Inside was soft and warm and now I wanted my dick in it. I withdrew my face and kissed her butt cheeks. Now standing up I started finding a way into it.

I was nervous honestly admitting, I couldn’t penetrate even though I was rock hard. Partly because of the tightness and partly because it was my first time. So I asked her whether she has a lube. In response she spat saliva on her hands and applied it on her ass. I tried again only to fail at this attempt.

Soon I realized that my cock was dry. So I spit on my hand and lubed my rubber covered member and started rubbing it around her hole. This time she used her hand to spread a cheek aside making it easier for me. And Eureka, it is in. I could at that very moment feel her sphincter rub against my glans.

At this point I knew my dick was in her. So I start thrusting myself I could feel her sphincter tighten over my shaft. At this time she brings her arm behind grips my ass and says, “Don’t let it out now.’ I was hard and inside her and thrusting. She was now moaning asking me to thrust harder and deeper.

It was a frustrating Sunday evening in September. I had been to the market picking up medicines and groceries. I had no plans for a sexual escapade anytime soon. Rather I was hungry and in need of a cold beer and some smokes. I ate some finger food in the market making my stomach ready for a nice cold beer.

I drove around the town sipping on beer and smoking, noticing the everyday stupidity of people around. Also in my plans for the evening was to refuel my car as it was nearing to running on fumes. It is a long line usually to wait for your turn at the gas station but it was short this time.

And on many occasions whilst waiting in such lines, smoking I had noticed crossdressers prostituting themselves. In the dark side lane adjacent to the road where everyone will line up for a vehicular refuel, these finely dressed trans genders will ask people to come.

Men, young and old, rich and broke all will make rounds in an impression to find a prostituting woman. But will turn away after knowing the reality. But some who will go try them will come out happy and pleased. I had noticed this for quite a while ago.

And so tonight I was planning to venture near them and try their services. I have tried straight hookers a couple of times. They are abusive ill-mannered bitches with no regard for your purpose of attaining pleasure. So I felt like trying these cross-dressing hookers once.

Instead of driving into the usual lane, I drove straight into the side lane. No one was there until the end of it. I could see them sitting on a wall in complete dark, four of them chatting amongst themselves. I had my target locked. Turning around I switched to the main lane and got my car refueled.

It must have taken ten minutes or so, the longest of my life. I had a couple of condoms on myself and decided to use them instead of what the hookers usually provide. I doubt that they reuse them. Safety before pleasure is necessary. I request the reader to keep safe sex a priority because you have only one life.

Anyway coming back to the scenario I was building up. I parked my car a few paces from the station. I took the exact amount of money I supposed will be needed. I placed my phone in the glove compartment, locked the car, and started walking. I went up to them and in a rusty dialect I asked about the charges.

They must not have got what I said and with politeness one of them asked me what I said. This time I politely asked how much would it cost. It was what I had supposed it to be. So I gave them the cash and followed one of them. As a part of the deal I told that the rubber to be used will be mine.

It jumped over a wall just about 3 feet high into what I figured out was a park, now dark and deserted. As soon I entered the place I took no shame in unzipping my pants and taking out my limp member. I started stroking it in an attempt to harden.

I followed her for a few paces after which she stopped between a few trees and bushes. Still stroking my penis to make it hard I asked for her name. She was shying to tell but still replied and asked my name. After these obligatory exchanges that are usually not customary I simply took her name.

I said, “Please pleasure me.” She replied with a small laugh and caught hold of my dick. To my surprise unlike the hookers I had encountered in the past, her approach was gentle. She gently took a grip of my shaft and started stroking it.

Now I am duty-bound to describe this ‘Shemale’ to the readers. Must have been 5’10 and built more than average. Had sharp features, dusky skin, and had the right amount of makeup to hide the masculinity.

She hadn’t stuffed rag under her clothes to make up for breast. Instead what appeared that she must be administering herself hormones quite common amongst the transgender. She was wearing a red salwar kameez or ladies suit commonly worn in my country.

She had a particular fragrance that was floral. though not smelled very costly but also wasn’t a cheap one, must have been ittar. Whatever, all this made me nervous and excited. I always had an attraction towards shemales and trans men.

Now gently stroking me she can make my dick hard, but still it isn’t at its 7 inches of length that it attains. She now asks for the rubber and places it on my dick. She asks me to pull my pants and boxers completely down and reveal my member to her completely.

I do so and as my pants fall revealing my legs and crotch she gently moves her hand caressing my thighs and my butt. Her touch is so warm and gentle that it sends me into a fit excitement that makes my legs tremble. Caressing my waist, thighs, and butt with one hand and stroking my penis with the other she looks at me.

She asks me to be calm. I try to control my trembling and take deep breaths. Seeing that I am ready to go she takes my dick in her mouth, slowly using her lips to press against my glans. She uses the same motion but increases the pressure each time.

She starts to blow me full-fledged as a professional, stroking my shaft with a hand and pressing her lips against my glans. My dick head is now swollen and I notice that she took a few nibbles on it, a pleasure I have never encountered. I am trembling and my legs are shaking.  She again asked me to calm down.

I take control of my legs and straighten myself up. At this she goes back to work sucking my dick applying the right pressure and strokes. She looks me in the eye while doing it and it complements her with grunts, moans, and by saying, “It feels so good.”

She stops smiles at me and grab hold of my balls and says, “Yes, it’s fun,” and gets back to work. This time with more fervor and intent as if she was enjoying pleasuring me. Now things were in a perfect tune her mouth worked my penis. One hand was caressing my right thigh and waist.

And her other hand was gently squeezing and rubbing my balls. I was so aroused and excited. I rose my polo shirt above to my chest leaving my midsection completely naked. Noticing this lust ignited in me she started to deep throat me.

She left hold of my balls and start rubbing both her hands on my tummy gently cratching it with her nails. She stops to catch a breath and at this moment I asked, “How is my dick, is it good?” She gives a nice look holding it from the end of the shaft.

My member now completely engorged with blood pleases her sight. She asks, “Will you fuck me with it?” At first I was not able to figure out what she said. But when she repeated those words I knew what she wanted. Crossdressers usually pleasure their patrons with a blowjob.

They are skilled at it and make people orgasm and discharge by just oral skills. But my penis at a length of the 7 inches and a girth of around 3 inches must have been something exciting for her. I said, “Yes I will love to put this into you.”

She gave me a four or five strokes deep throat and stood up to undo her salwar. She drops it down as she turns around to reveal a behind that was thick and round and as shapely as it should be and utterly feminine. She bends over and spits on her fingers and applied the saliva between her butt cheeks.

With this act I could figure out how tight her butt is as it didn’t yield even a bit. Her fingers disappeared in between its two halves.