An Expensive Addiction Ch. 02

A week went by following my first encounter with English, my tranny escort, before I found myself craving another. Every day when I jacked off I thought of her sexy slender body and that big thick, long, uncut cock. The feeling of her hands running through my hair and then pushing on the back of my head to force her cock into my mouth...then the incredible sensation of having her cock spurt a huge load of hot tranny cum as she forced me to swallow it all. Just thinking about it made my cock hard. I knew that I was going to be seeing her a lot more, and just hoped that I could control myself enough to keep my addiction a secret. There was no communication between us following that first time, and I figured that was normal considering she was an escort. I saw her ads posted on the escort pages and wondered how many other guys she had forced to swallow her cum since I had. In a way, it kind of made me a little jealous, but again I reminded myself that she was an escort.

Work that week flew by, and I got enough done that I was able to get back to town on Thursday instead of Friday. My girlfriend was coming in this weekend for a party on Friday night, so I was excited about that. We hadn't seen each other in two weeks so it was a given that she would want to have sex Friday before the party. While that thought got me horny, I couldn't help but let me fantasies drift back to English. I knew that I needed to see her soon. Once I got back to my apartment that Thursday I touched base with all of my buddies to see what their plans were. As usual all they wanted to do was get stoned and go out to the bars, but I decided to play it cool...I had other things in mind for my evening. I got off the phone with Dan after I told him I was going to take it easy, and thought about calling English, but decided to have a beer first.

Once I sat down at my desk in my office with that cold beer, I pulled up English's ad on the escort site and saw that she had taken a new picture! She was wearing that tight blue corset again with some fishnet stockings and her tall platform heels again. I started to feel anxious as I pulled out my phone and dialed her number, but before I pressed "Call" I finished my beer and grabbed another from the fridge. When I got back into the office I sat down in my desk chair, picked up my phone, and called her. After 5 rings her voicemail picked up, and it was the standard "you have reached the voicemail of nine five one....yada yada yada" message. I hung up, disappointed.

Since she seemed to be pretty text friendly, I sent her a text saying, "Hey English this is Joe, I met you last week at your place. Would love to see you again tonight, let me know if you're available." Maybe it would be a good idea to watch a movie and get to sleep early tonight, tomorrow night was going to be a long one at that party. I drank my second beer hoping to hear back from English, but once I went to the kitchen to get my third and hadn't heard anything I figured it was a bust. With her escort ad still pulled up, I opened a new incognito browser window and went to my favorite porn site to find a good video. My cock was semi-hard already, leaking precum into my boxers. Once I went to the "Tranny & She-male Videos" section, my cock was hard as a rock.

I pulled down my boxers and started jacking off to a video of a shemale pounding two different guys asses with her big cock. This girl was really getting into it, slamming her cock balls deep while the guys groaned for more. I started pulling on my balls with my other hand to keep myself from cumming too soon, I wanted to watch more of this video before I blew my load. When the shemale pulled her cock out of one guys ass and jammed it in the other guy's mouth, I felt my orgasm start building. That was incredibly hot and turned me on so much I couldn't control myself, a few seconds later I was spurting cum onto my hands and the floor in my office. Thankfully it was a tile floor, so cleanup was easy once I went to get a tissue from the bathroom.

Deciding that I should try to distract myself from jacking off for awhile I went into the living room and started looking for a movie to watch. A few minutes later I started my fourth beer and found a film, turned it on and got comfortable on the couch. One of my buddies texted and said I should come join him at the bar, but I didn't bother responding. Engaging those guys just gave them the idea that with more peer pressure they could get me to come out, so it was best to just ignore them. After an hour or so of the movie I had finished that fourth beer and fallen asleep on the couch. I'm not sure how long I was asleep before my phone started ringing, waking me from my sleep. As I sat up on the couch and grabbed my phone, I saw that it was English calling me back.

A momentary panic set in for a variety of reasons, first I was nervous as hell to see her again, second I thought it might be too late already, and third I was feeling buzzed and tired. I answered though, and sheepishly said "Hello?"

I heard her husky voice again, "Hey Joe, it's English, how's it going?"

"Things are going good, I was just watching a movie and having a beer at my apartment," I replied.

There was a pause before she said, "Well do you still want to see me tonight? I'd love to see you again sexy..."

Now I was getting turned on, but I thought about saying no because I knew I should just go to bed at this point. I didn't though. "Yes baby, I would love to see you. I've had a few beers, could you come to my place this time?"

"Sure, that sounds good, but I won't be able to come for an hour or so, and the donation will be 200 for an outcall." I didn't really want to wait an hour, so this time I was the one who paused.

But I was really horny and knew I wanted to see her, so I said, "Yeah that's great, I can take a shower and get ready for you. Could you wear that blue corset with the outfit from your new pic on that ad?"

She giggled and replied, "Sure sexy, I'll wear that outfit just for you. Text me your address and I will let you know when I'm on the way."

We got off the phone and I sent her my address, then decided I should smoke a bowl to calm my nerves before I got into the shower. Taking a shower while stoned was always a great feeling and would be a good way to pass the time. After I packed the bowl and took two hits I got into the shower, letting the hot water and steam wash over me. Strangely my cock wasn't hard, but I didn't think much about it. Once English got here, that wouldn't be a problem. About 20 minutes later I got out of the shower, and as the steam rose off my wet skin I realized how drained I felt. There was a 5 hour energy in my fridge so I walked to the kitchen, chugged it, and went back to the bathroom to finish drying off.

After I got dried off and dressed, I went back into the living room and sat down on the couch. I checked my phone, and it had been almost 45 minutes since English had called. The nervousness started creeping up again and I could feel that 5 hour energy mixing with the four beers in my stomach, which was starting to gurgle. Not a good sign...I just hoped that things would calm down before English got here. I went to the bathroom and ate two Tums before going back to the couch. Sportscenter was on so I got caught up on the world of sports and tried not to check my phone every two minutes to see if it had been an hour yet. By the time an hour had passed since our phonecall, my stomach was turning over and I knew I had to take care of that situation.

15 minutes later I emerged from the bathroom feeling much better, but I still hadn't heard from English. I sat back on the couch and waited to hear from her. After awhile, despite the 5 hour energy, I fell asleep again. Just like before, my phone woke me up an hour later, and of course it was English. After I answered, she said that she was close to my apartment, but had taken a cab and needed me to come outside to pay for it. I wasn't too thrilled about that, but there wasn't much I could do at this point besides put my shoes on and head outside. 5 minutes later her cab pulled up, and I walked over to the cab drivers window. English got out and came up behind me while I paid the driver with my credit card, because the only cash I had was her donation.

Once the cab had left, we walked into my apartment and I closed the door. English reached by me to turn both deadbolt locks, and I noticed that she was wearing an overcoat style jacket that went just a little past her knees and was tied at the waist. She had on those platform heels I asked her to wear, and I could see the fishnet stockings too. After a brief kiss and hug, she stepped back and untied her jacket, dropping it to the ground to let me observe her beautiful body in that tight blue corset. She had on a very short black miniskirt that was covering the garter belt holding up her stockings, and looked like the hottest thing I had ever seen. As she saw the lust in my eyes she started grinning, then pulled me closer for another kiss while she wrapped one of her legs around my waist. Once our kiss ended she asked me, "is that weed that I smell?"

"Yeah, I smoked some after we talked to calm myself down...I hope that's not a problem," I replied.

She cocked her head a bit to the side and smiled, "of course not! It smells good, do you have some that I could take a hit of?" I led her into my office and packed a bowl in my bubbler. She took a big rip, held it in like a pro, and exhaled a huge cloud of smoke.

She coughed a second, and then said, "that's some good shit! Weed always gets me super horny. Do you have something I can drink? Water is fine, but I'd prefer a coke..."

I went to the kitchen and retrieved a coke for her and a beer for myself, then walked back into the office and sat down on the couch. She came and sat next to me, opened her coke, took a big swig, set it on the table, and leaned towards me for another deep kiss. As our tongues tangled with each other she gently reached down to massage my cock through my jeans and boxers, then she grabbed my balls and squeezed them. I reached over to her cock and massaged it to return the favor, and I could feel her getting hard through the thong under her miniskirt. She stood up, took another swig of her coke while I took a chug of my beer, and then she slowly pulled down her thong, letting her cock swing free.

She sat back on the couch and I knew that she wanted me to suck on her big uncut shemale cock, so I got on my knees between her legs and gripped the base of her shaft with my right hand. I gently massaged her balls with my left hand, and slowly started taking her cock head into my mouth as I pulled down her foreskin with my hand, pumping her shaft as I took the head deeper. She moaned and started running her fingers through my hair, and in no time she was face fucking me again. From this angle I really couldn't take her cock into my throat, and was starting to gag everytime she pumped into my mouth. "Good boy, take my cock, I want to feel you gag on it. Get it sloppy with all that spit!" No problem there, my mouth was watering and heavy thick saliva was starting to stream down to the base of her cock.

After a few minutes of that, she asked if I wanted to head to the bedroom. Before we left the office she took another swig of her coke and then another hit from the bubbler. We walked down the hall to the bedroom and she told me to take off my clothes and lay down on my back on the bed. I complied, then she asked, "Can you turn on some music? I like rap." I got my phone off the bedside table and turned on a rap Pandora station on my bedroom stereo. She set her bag down on the foot of the bed, then took off her miniskirt but kept on the heels, stockings, garter belt, and corset as she climbed onto the bed and got between my legs. My cock was at full mast when she started sucking on it, and after she deepthroated me a few times I felt her finger pressing on my asshole, just like last time.

"I don't know if I'm ready for that yet baby..." I told her. She went back to pulling, squeezing, twisting, and massaging my balls and left my asshole alone.

A few minutes later she told me, "Roll over onto your hands and knees, I want to eat that sexy ass!" I had never been rimmed before, but was so turned on I thought it could be a fun experience. Once I had turned over and gotten into the doggy position, she grabbed my cock from between my legs and started slowly squeezing and jacking my shaft, then I felt her breath on my hole...it kind of tickled. The first time her tongue touched me I flinched away a little, but she used her spare hand to pull my hips back and started flicking her tongue back and forth over my hole. It felt absolutely amazing! I never would have imagined that someone licking my ass could feel so great! She licked around for a minute, and then stuck her tongue just a bit inside my still virgin hole. That was a crazy sensation but it felt awesome and I didn't want her to stop.

She kept it up for a few minutes, and then pulled her head back away from my ass. I felt her finger massaging around my wet hole, and then gently pushing inside. This time I didn't protest, she obviously knew what she was doing and I was loving it. My cock was pouring precum all over the sheets while she gently jacked it off, slowly working her finger all the way inside me. I heard her husky voice say, "yeah baby, you like that don't you?"

I couldn't lie, and panted, "yes, I've never had anything in my ass before your finger last time, but it feels good..." She giggled, and then started to push her finger in and out, slowly fucking my hole with it. I was really into it, and was getting more turned on with every stroke of my cock and each thrust of her finger. She knew exactly what I wanted...

"English, will you fuck me? I want to feel your cock inside me, but you need to go slow since it's my first time..." I sheepishly asked.

There was a short pause before she answered, "yes, I want to fuck that sexy ass, but you need to suck my cock some more to get me hard again. And I want to get a water, you stay here, I can get it myself." She got off the bed, walked into the kitchen and I heard the fridge open. I positioned myself on my back, with my head hanging off the side of the bed so that she could face and throat fuck me with that big cock when she got back. As I was getting situated and preparing myself to be throat fucked, then ass fucked, I thought I heard a cabinet open in the kitchen, but didn't think much of it. She walked back in the room, and was on the other side of the bed from which I was facing, but was very pleased with my new submissive position. I heard her set something down on the bedside table and then she walked around to my side of the bed.

She lined up that big cock with my mouth and slowly stepped forward, pushing into my mouth. Instead of pushing deep into my throat like I assumed she would, she pumped her shaft while just the had of her cock was in my mouth, then pulled out and started slapping my cheeks with her thick uncut cock, leaving my spit and saliva running down both sides of my face while she said, "yeah, take my big cock you slut!" I got really turned on by this, and reached around her legs to pull her hips towards my mouth once I got her cock back in my mouth. She needed no more encouragement than that, and was shortly giving my throat full thrusts with her long shemale cock, pushing past my mouth and into my throat with the head of her cock, and holding tightly to the back of my head as I gagged and choked on it, before pulling out to let me take another breath. Saliva was running down into my eyes but I was absolutely loving this dominant side of her. She pushed into my throat and then I felt her lean forward over my body, holding my head on her cock with her right hand and reaching for her bag with her left. I heard her reach around in her bag for a second before she stood back up and released my head so I could gasp for air.

Then her cock was pushing back into my mouth, and I heard the "ding" of an iPhone starting to record a video. I started panicking at this point, but she grabbed my hair with her right hand and thrust deep into my throat, gagging me and cutting off my air supply before I could say anything. "Shhhhh, take my cock you slut! You're doing so good I wanted to get a video, I can see the head of my cock in your throat and it looks like you're trying to swallow it!" I was really starting to panic since my air was cut off, and I could feel blood rushing to my head. She pulled out of my throat for just a second, and then as I took one ragged breath from around her thick uncut cock, she twisted my hair in her fist as she plunged back into my throat. Then she held her cock there for what seemed like an eternity, as I repeatedly gagged on the thick invader. Despite the fact that she was getting more aggressive than I had wanted, I was still really enjoying this.

As she stepped back away from me and her cock slid from my mouth I heard her phone stop recording. I coughed a few times and took some deep breaths before sitting up on the bed. She walked around to the other side and started climbing up onto the bed with me. "Get on your hands and knees again, slut!" I complied, and I heard her digging around in her bag again. She ripped open a condom, I heard her roll it onto her thick she-stick, and then I heard her pop the top open on a bottle of lube. The lube was cold, and as she squirted it onto my waiting hole I flinched. I felt her finger push into me again, this time with much less resistance, and she fucked me quickly with her finger for a few thrusts. Then her finger was removed and I felt empty, knowing that I was ready to take my first cock! She put the head of her cock up against my hole, repositioned herself behind me, and started pushing.

The pressure on my hole built up for a minute, and then all of a sudden the head of her cock popped into my virgin hole. It didn't HURT, but it burned, and I let out a long sigh. She spanked my ass cheek and said "you're doing good slut, I'm going to go slow, don't worry." She held her cock head just inside my hole for a minute or two, before she started pushing in further. Now it started to hurt, but I wasn't about to tell her to stop, I wanted to feel her whole cock inside me. I pushed back a bit once I had an inch or two of cock inside me, and she thrust forward to bury three quarters of her thick nine inches inside me. The pain was subsiding but my ass was still burning. To distract me English reached between my legs and started roughly tugging on my half erect cock, getting me back to full erection as she pushed deeper into my ass.

Once I felt her balls touching mine, I knew her entire cock was inside me. I felt so full, like I needed to take a shit, but I was loving the sensation of having a cock in my hole. She started to pull back out slowly, and then pushed all the way back in. After a few very slow pumps, she started building up speed. I started began pushing my hips back to meet her thrusts, and the burning sensation subsided, she was actually fucking me now! Every minute or so she would reach between my legs to jack my cock again, keeping me almost fully erect the entire time. She really started to thrust into me once we got a rhythm, and I could feel her balls slap up against mine as she shoved her entire length into my hole. She kept up this steady pace for a few minutes, and then I felt her lean back and fish around in her bag again. Wondering what the hell was in store for me this time, I tried to look back at her. "Keep facing forward bitch!" Yes ma'am...jeez! She was really in charge of this situation.

Then as she reached between my legs and started jacking my cock with hers fully buried inside me, I felt her lean forward and reach around my waist with her other hand. Something cold and hard touched the tip of my cock, and I tried to jump away, but she had me pinned on her huge cock so I was only able to impale myself more trying to escape this weird sensation. The pumping on my cock got more furious, and I realized that this cold hard thing was some kind of glass that she had stuck the head of my cock into...and I started to understand what she was doing. After about 30 seconds I started trembling, and said "English, you're about to make me cum..."