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Prositutes – lingerie – hookers – transsexual first time – butt plugs

I have a little problem.

Well, to be honest, it's more than just a little problem. Some might consider it to be a huge problem.

I am addicted to prostitutes.

I have been pretty much all of my adult life, since I first walked out of the front gate at Lackland Air force Base in Texas and saw a pretty young girl sitting on the hood of a car in front of a massage parlor. When I glanced over at her she had slipped her shorts aside and exposed her hairy vagina, and I had followed her into the massage parlor and shelled out $30 to fondle her breasts and get a blowjob that lasted all of about two minutes. Don't be too judgmental - I had just completed six weeks of basic training in the Air force and had a little bit of pent up emotion, if you know what I mean.

I was not a virgin, but I had lost my virginity about a week before I went in the service to a girl I was deeply in love with. She had entered my life at the end of my senior year in high school, split me up from my high school sweetheart who I had been dating for two and half years, and made me fall helplessly in love with her. By the time we took each other's virginity, we were engaged to be married. She called it off by telephone during my last week of basic training, breaking my heart and leading me into the arms of my first prostitute.

I had done a lot of fooling around in high school, lots of touching and fingering, and an occasional hand job or blow job, and I had even experimented with gay sex in a relationship that lasted on and off for three years. I'm sure you understand when I say that it's hard work getting laid. Searching, finding the right person, the inevitable pursuit, spending money, and all the other bullshit associated with hooking up with a partner who may or may not have sex with you at sometime in the near (or distant) future.

Prostitutes just seemed like an easier way to get what I wanted when I was 18 years old. I could skip all the steps except the spending of money and have my needs met pretty much whenever I pleased.

You can find a prostitute anywhere in the world. Sometimes they're available in significant numbers right out on the streets. Other times and in other locations they are a little harder to find, but you just have to know where to ask and someone can usually steer you to the small town hooker who can take care of your baser needs.

I spent the next four years at a couple of different locations in Europe and there were more than enough prostitutes to go around. Outside the front gate of the Air force Base I was stationed at was a quaint little place called the Annabella Haus. It had a bar in front with scantily clad waitresses and porn on the big screens, and then you could go out back to the hotel, where the prostitutes sat outside their rooms. You just walked around until you found one you liked and into the room you went. For the right price, you could have just about anything you wanted. Luckily they had a pretty high turnover of girls; otherwise I would have run out of new partners.

Not far away was the Lisa Bar. It wasn't a strip club, but when you walked in the Vietnamese girls practically ****d you while you bought them small glasses of colored water for $10. They worked hard to get you into the Champagne Room, where for $100 you could have sex with a beautiful Asian girl, or even two, if you had the dough.

If you just wanted a quickie, you could drive down Forty Mark Strasse and pick out a prostitute hanging out on the side of the road, usually smoking a cigarette. She would hop in your car and give you a fast blowjob. Or if you were feeling particularly flexible and had a little extra cash, you could fuck her in the back seat of your tiny European car. Forty Deutsche Marks was about $32 when I first arrived; by the time I left, it was $18 due to the rapidly changing and favorable exchange rate.

There was a Red Light District in every major city in Europe. Some, like in Hamburg or Amsterdam, were famous and even the tourists wandered around ogling the beautiful girls sitting in their windows waiting for the next customer. Others, because of some ridiculous law or another, were more difficult to find. But eventually, I always found them.

I had sex with hookers in almost every country in Western Europe. I had a few girlfriends, but nothing that lasted. Hookers never said no, never wanted to chat about how your day was, and never insisted that you engage in "the pursuit" before they agreed to climb in bed with you.

But I'm straying from the intent of this story. By the time I returned from Europe, I was addicted to prostitutes. I ended up in Las Vegas for awhile, where you could spend a whole night with a streetwalker for $50 or spend your life savings on a high class prostitute who charged thousands of dollars per hour. I tried some of both and everything in between, but although I had high class desires, I was on more of a $50 budget.

After a couple of years I transferred to Miami, where my salary finally approached high-class levels. You could find high-class hookers in Miami, but there were also a lot of the $50 variety as well. Northeast 79th street from Interstate 95 eastbound to US1was a treasure trove of streetwalking hookers who were usually more than enough to satisfy my basic instincts.

I tried marriage. Met a beautiful Cuban woman working in a bar I frequented. She was going to law school during the day and working the 7:00pm to 3:00am shift at the cocktail lounge I frequented. We started out flirting, moved on to more substantial conversation during slow times at the bar, had what we thought would be a one night stand, and ended up married about six months after we met. She was amazing in bed before we got married. After we spent $30,000 on a wedding and $25,000 on the honeymoon, she lost interest in sex and especially in the amazing blow jobs she had always been willing to give when she was busy reeling me in.

Driving home late one night after spending most of the afternoon and evening in a bar, I cruised down 79th Street and spotted a beautiful blond with huge tits and tight red shorts and couldn't help myself - I circled the block and pulled up next to her.

"Want a date?" She asked when I rolled down my window. I wasn't interested in just a blow job. This girl was young, gorgeous, and a rarity on 79th Street - white. I don't mind black hookers at all. I have fucked hundreds of them, but on that night that white girl caught my eye because of the color of her skin. In that area the prostitutes were mostly black, and I had subconsciously decided if I was going to shatter my marriage vows, I wanted to do it with a white prostitute.

I asked if she had a place nearby, and she indicated the run-down building she was standing in front of. She asked if I was a cop, and I assured her that I was not. "Forty for a blowjob, a hundred to suck and fuck," she said, chewing on her gum loudly.

"Suck and fuck," I said and she opened the door and got in. We drove around the corner and parked and she led me into the "hotel" as she called it, and I admired her perfect ass as we walked up a flight of stairs. The stairwell was filthy and smelled of piss. She led me through a door at the top of the stairs that turned out to be a bathroom. There were three stalls in various states of destruction as well as three busted urinals on the wall. It was no cleaner than the rest of the place but there was an old leather sofa cushion on the floor which turned out to be where she plied her trade.

We took care of the finances, and she squatted down in front of me as I leaned back against the one remaining intact sink. She unsnapped and unzipped my pants and pulled them down, along with my boxers. I was already erect, and she smiled up at me and spit out her gum, and then took my cock in her right hand and wrapped her lips around it as she cupped my balls in her left.

She gave great head, and I had to stop her several minutes later before I came. She moved over to the sofa cushion and lay on her back, hiking up her skirt to reveal that she was not wearing panties. I shuffled over to her with my pants around my ankles and knelt on the front edge of the cushion. She reached down and guided my cock into her shaved pussy, which was surprisingly wet. I eased my cock inside her, she started making the obligatory noises, and I came about five minutes later. It was the early 80's then, and the fear of AIDS hadn't quite forced the streetwalker community into widespread use of condoms yet.

I stood up and she held out a hand for me to help her up. I pulled her to her feet and she pulled down her skirt and kissed me on the cheek. I pulled up my pants and boxers and gave her a $20 tip. I turned to walk out as she went to the broken mirror and began adjusting her makeup.

I went down to my car, circled the block, and parked about fifty yards away on the side street beside the hotel. She came outside a few minutes later and took up her station on the corner. About a minute later, someone else had stopped and soon thereafter she was leading him into the hotel. I sat and watched for almost two hours and she led eight different males into her love shack during that time period. I had decided after I left her the first time that I wanted to have a second round, so I had waited and watched until I was fully recharged. After she came back out and resumed her station, I pulled up to her and rolled down the window again.

"Want a date?" She asked in a bored voice, not even recognizing me. I said I did and we went through the same ritual and a few minutes later I was handing her another $100 in the dirty bathroom upstairs. There was a small pile of crumpled up Kleenex on the floor that I hadn't noticed before. I turned to the sink to wash my hands only to discover there was no running water. It was then I figured out why she had been so wet before - she was simply wiping off the outside of her pussy with Kleenex after each customer. The inside? Well, you get the picture.

She spit her gum out again, took my hard cock out of my pants, and gave me another outstanding blowjob. After a few minutes she stopped and went back to the cushion and lay back just like before. I once again shuffled over to join her, knelt, and she was soon guiding my cock into her even wetter pussy. I thrust forward into her, and she closed her eyes and laid back. I said I wanted to kiss her, and she informed me that would be another $10. I had to pull out, retrieve my wallet and pay her before we could continue. I re-entered her cunt and leaned forward to kiss her and she said, "Not on the mouth."

I kissed her cheeks and her neck while I fucked her, and I came about ten minutes later. Once again I helped her up, dressed, and gave her a tip after she kissed me on the cheek. As I was walking out she said "Don't I know you from somewhere?"

I drove home, feeling dirty physically and mentally, and kicking myself in the ass for cheating on my wife. When I got home I stripped naked, threw my clothes into the laundry hamper, and climbed into bed next to my sleeping wife. I fell asleep feeling sexually satisfied, but deeply unhappy.

All this is still not the point. You haven't yet met the title character of this story. All that has come before was simply to convince you that I actually have an addiction. In any other addiction, that night would have probably been labeled my "rock bottom," at which point with the proper help I could begin climbing out of the nightmare I was in. I haven't yet managed to find a cure, although a lot of years have passed since then.

In the morning, my beautiful Cuban wife woke me up screaming at me and hitting me. I stumbled out of bed and into a corner, standing naked and trying to defend myself from the 120 pound monster she had turned into. She was so angry she was screaming at me in Spanish and I couldn't understand what she was saying. I did understand the language, but she was screaming and talking really fast so I had no clue why she was so upset.

She finally held up my white boxers and showed me a red stain. "There's fucking lipstick on your fucking boxers, you fucking prick," she said in English in a slightly less loud voice. Then she pointed at my crotch and screamed, "And you didn't even bother to wash your dick, hijo de puta!"

She stormed out of the house with my boxers and my shirt, which I found out later via her lawyer, also had lipstick on the collar. She had even had the presence of mind, before she turned into the satanic creature that had awoken me from a deep sleep, to take pictures of my lipstick-covered cock and the lipstick on my face. My lawyer advised me to settle quickly and she got just about everything.

So, many years and hundreds of hookers later, I was once again driving down 79th Street to the small apartment I had been living in since my divorce. It was almost 6:00am and I had been drinking since I got off work at midnight. Most of the hookers had called it a night, but those who were still out didn't appeal to me. I cruised up and down 79th Street a couple of times and then decided to head home.

I turned onto Biscayne Boulevard heading north. There was a Laundromat on the right-hand side about three blocks north of 79th Street. As I passed it I glimpsed a perfect ass in a miniskirt bent over in the parking lot. I slammed on my brakes for a better look, and the girl stood up and looked over her shoulder at me. She looked beautiful, and I immediately pulled into the parking lot. She stood back and waited while I eased up next to her and rolled down my window.

"Hi honey," she said in a slightly husky Hispanic accent, "you looking for a date?"

"I am," I replied.

"You're not a cop, are you?" She asked.

"No, not a cop," I replied for perhaps the thousandth time. "Just looking for some company."

"Well," she said as she opened the door and got in, "you're in luck. I was on my way home. If I hadn't had to stop and fix my shoe, I would have been gone already."

"I feel lucky," I responded, and she laughed, pulling the door closed behind her.

I took a close look at her while the interior light was on. She was very pretty and looked amazingly like the Hispanic actress Rosie Perez. She had curly, brown hair that hung just past her shoulders, brown eyes, high cheekbones, and big dimples. Her skin was light brown and what I could see was flawless. She didn't have big tits like Rosie Perez, but the short glimpse I'd managed of her ass and legs when she was bent over fixing her shoe had revealed they were perfect. She was wearing a pink mini-dress with no straps and when she sat in my car the skirt had ridden up just enough to show me the tops of her sheer black stockings. Black garter straps held the stockings in place and I wondered what the rest of her lingerie looked like as my cock swelled.

"You're gorgeous," I said and she laughed again.

"Thanks, handsome," she replied. "My name is Peaches."

She held out her hand and I shook it. "Mike," I lied.

"Well, Mike," she said as she reached a hand into my crotch and smiled when she felt my erection, "unfortunately, my roommate is already home so I can't invite you back to my place. I can offer you a blowjob for $60 and if you like it, maybe you can track me down tomorrow night for more."

When I said that sounded good, she told me to turn right out of the parking lot and gave me directions to a secluded cul-de-sac with no streetlights. I pulled over where she indicated and shut off my car. I leaned my chair back and she got on her knees and unsnapped and unzipped my slacks. I lifted my ass and slipped my pants and boxers down to my thighs. I was rock hard and I placed my hand on the back of her head as she lowered her face to my crotch, licking the head of my cock. She then wrapped her lips around my cock and started to lower her head, but then sat up.

"Almost forgot," she said with a smile, "cash first.

I reached down to the back pocket of my pants and did not feel my wallet. I tried the other back pocket and no luck there either. I started to panic and began fumbling in all my pockets, only to discover my wallet was not there. Peaches sat back and watched as I searched frantically. I pulled my boxers and pants back up, and then got out of my car so I could search the floorboards. Peaches was not happy about the light coming on while I looked, and told me to hurry.

My wallet was nowhere to be found. I looked at her and asked, "Did you take my wallet?"

"Fuck you," she replied. "I didn't take it."

"I just had it," I said, now convinced she had taken it when she had been groping me on the drive from the Laundromat.

"Well, I don't have it," she snapped, and opened her small purse to prove it wasn't in there. Then she pulled down the front of her mini-dress to show me it wasn't there, exposing her small breasts and huge nipples. Then she hiked up her skirt to show me it wasn't in her crotch either, revealing very sexy black lace panties and matching garter belt. She had a little nature trail of curly hair on her flat stomach that started just above her belly button and disappeared into the top of her panties.

I was hornier than ever, but I had no money. I apologized for accusing her, and asked if I could drop her off somewhere. She rearranged her clothing as I got back behind the wheel and started the car. She gave me directions to a group of rundown apartment buildings and told me to drop her at the curb. She stood there waiting for me to drive away before she turned and walked to her apartment, presumably so I wouldn't see where she lived.

I was so angry I couldn't stand it. I was extremely horny and had been thrilled to run into her so late. She was much better looking than the average streetwalker, and from what I had been able to see she'd had an amazing body. The brief period of time her full lips had been wrapped around my cock had convinced me that she was worth the money.

I drove home; still not completely convinced she hadn't somehow lifted my wallet. I thought about the hassle of losing my wallet - all the calls I would have to make to cancel credit and debit cards, get a new voter ID, and a trip to the dreaded Department of Motor vehicles for a new driver's license. And I hadn't even gotten a blow job. I was definitely not happy about the way my night had ended.

When I arrived home I made a pot of coffee and started calling my credit card companies. I had canceled two of my three credit cards when I remembered the last time I had seen my wallet was when I paid for my expensive drink tab from the bar. I decided to postpone making any more calls until the bar opened and I could call and see if I'd left my wallet there. They knew me pretty well and I thought that if I had left it there I had a good chance of getting it back intact.

I crawled into bed and jacked off, fantasizing about Peaches' perfect ass.

I woke up just after noon and called the bar. Sure enough, I had left my wallet on the bar and they were holding it for me. I told them I would be in later to pick it up, and then I planned my night. I would go to the bar about 8:00, have a few drinks, and then go looking for Peaches about midnight.

I spent the day, which was Saturday, cleaning my apartment, paying some bills, and went for a run in the early evening. After a shower I dressed and headed to the bar. I collected my wallet, very thankful that Peaches hadn't stolen it, and spent the next five hours drinking with my usual crowd. When I realized the time, I paid my bill and headed out. Everyone was surprised that I left so early.

I cruised up and down 79th Street for the next three hours looking for Peaches but never found her. I even stopped and asked another hooker if she knew Peaches.

"I can be Peaches for you if you want," she replied, "but I don't know anybody by that name."

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tagTranssexuals & CrossdressersPeaches and CreamPage 2
Peaches and Cream
byBiDrew42©
Frustrated, I decided to call it a night and turned onto US1 to head home to my apartment in North Miami Beach. Just before I got to the Laundromat where I had seen Peaches the night before, a pretty black hooker flashed her tits at me and I pulled over.

"Want a date?" She asked.

"Actually," I replied, 'you're very beautiful, but I was wondering if you knew a girl named Peaches."

"I know Peaches," she said. "But she went home with a john and he paid her for the night. She won't be back out."

"Thanks," I said, disappointed. I put the car in gear.

"Don't go away baby," she said, pulling her top down again to reveal her large tits. "You know Peaches doesn't have tits like these."

I was horny as hell but I had my heart set on finding Peaches again and continuing what we'd started the night before.

"Sixty dollars for the best blowjob you've ever had," she said, "shaking her tits up and down. Hundred for a little suck and fuck, or you can take me home for the rest of the night for two hundred and do anything you want except anal. That's another hundred."

I was too horny to say no. She was by far the best looking hooker I'd seen so far that night, and it was getting late.

"Get in," I said, and told her I wanted to take her home for the rest of the night. She reached over and grabbed my crotch as I drove home. She did give an excellent blow job, but I ended up spending the extra hundred anyway.

Over the next three weeks, I looked for Peaches every night. She was nowhere to be found, although I had added the first few blocks of US1 north of 79th street to my nightly cruise. I had discovered that some of the newer girls liked the area better because of the bad reputation that 79th street hookers had acquired. I had to admit that the girls on US1 were better looking, and I fucked several of them during my quest for Peaches.

Just as I was about to give up hope of ever seeing her again, I saw her getting into a car in the Laundromat parking lot just before I drove up. I was pissed that I'd missed her, but I pulled into the parking lot hoping she would return after a quickie. She didn't come back during the next two hours that I sat there, and the cops finally ran me off.

The next night, success! I saw Peaches on the corner just north of the Laundromat. She had just gotten out of a Cadillac, once again about 6:00am. She was looking into a small mirror and fixing her makeup. I managed to pull up to her in front of another car that had just made a U-turn. Apparently, she was very popular. She was wearing a black mini-skirt and white top, with fishnet stockings and knee high leather boots. She looked amazing when she leaned down to my open passenger-side window.

"Well, hello again, Mike," she said, smiling. "Did you remember to bring your wallet this time?"

"Sorry about that," I replied, "I left it at a bar."

"You wanna finish what we started last time?"

"Absolutely," I replied. She opened the door and climbed in, leaning over and kissing me on the cheek.

"Heard you've been looking for me," she said with a smile. "That's sweet."

"I have been looking for you every night since then," I said seriously.

She looked over at me. "Why?" She asked.

I shrugged. "I wanted to apologize, for one thing. I wanted that blowjob, mainly. And I haven't been able to stop thinking about you."

Peaches studied my face for a moment, and then asked me if I remembered the way. I did, and we pulled into the little cul-de-sac a few minutes later. I handed over $60, and Peaches smiled and tucked it into her purse, removing a wrapped condom at the same time. Peaches got up on her knees as I slid my pants and boxers down to my thighs, and she kissed the head of my cock before slipping the condom on and rolling it down. Then she took my hard cock in one hand and lowered her lips around my shaft.

It was an amazing blowjob, even better than I thought it would be. Peaches used her lips and tongue to maximize my pleasure, at the same time stroking my shaft and fondling my balls. She was also accomplished at deep-throat, and could completely swallow my thick 7 ½ inch cock for lengthy periods of time. She had to work for her money though - I didn't come until about 15 minutes after she started.

After I had spurted into the condom, she retrieved a Kleenex from her purse and removed the condom from my slowly shrinking cock. She cleaned up my cock with the Kleenex, and then gave the head of my cock another kiss before sitting back down and arranging her clothes. I handed her another $40, and she leaned across and kissed me on the lips.

"Thanks, sweetie," she said. "I'm glad you found your wallet. And that your stalking me for the past three weeks was not because you're a serial killer. I was getting a little creeped out when someone told me almost every night that you were looking for me."

I laughed. "Yeah, I guess that was a little stalker-like."

I started the car and drove back to Peaches' apartment complex. This time she directed me to her building and I dropped her at the front door.

"I'd love to see you again, Peaches," I said as she opened the car door. "Maybe spend an entire night with you."

"Are you sure?" She asked.

I wasn't sure what she meant by that but I said, "Damn sure. You're gorgeous, and I want to explore the rest of you."

Peaches smiled, somewhat sadly I thought, but she consulted a small notebook and said she was available the following Saturday night from midnight on. Apparently she had a lot of customers who liked to spend the night with her.

"It will be a thousand for the night," she said, "which will get you far more than you bargained for."

I told her I couldn't wait, and that I would see her at midnight the following Saturday. She looked like she wanted to say something more, but then smiled and kissed me on the lips again and got out. I watched her ass sway from side-to-side as she walked up the stairs to her second floor apartment and my cock grew hard again. When she had opened the door, she turned and blew me a kiss, and then went inside and closed the door.

My addiction got the best of me that week and I got blowjobs from five different hookers over the course of three nights.

Saturday night I showered, shaved, and dressed in a good pair of jeans and a polo shirt. I arrived at Peaches apartment right on time. I walked up the stairs and knocked, but there was no answer. Just then a car pulled into the parking lot and stopped behind mine. Peaches got out of the passenger side and said goodnight to the john behind the wheel, then smiled and waved up at me as she closed the door. The car reversed out of the parking lot and I watched as she walked forward and started up the stairs, reaching inside her purse for her keys.

Peaches was wearing a red leather mini-dress with thin straps, sheer red stockings, and red stiletto heels. She looked stunning and my cock swelled as I watched approach. She smiled again as she reached me, kissed me on the cheek, and then opened the door and invited me in. I watched her perfect ass as she walked inside.

She pointed to the small kitchen. "Make us a drink while I clean up," she said, "I'll have a Cuba Libre."

I went into the kitchen as she walked down a short hallway and entered a room on the left, closing the door behind her. She had a few bottles of high-end Rum, but they would be wasted in a mixed drink, so I used the Bacardi and mixed two Cuba Libres, rummaging through her refrigerator for the Coke and lime. I took the drinks back into the living room and sat on the sofa, placing the glasses on the coffee table.

Peaches came out about 15 minutes later and walked into the living room. She had removed the mini-dress, and was now wearing only a red leather and lace corset, sheer red lace panties and matching garter belt, the sheer stockings and red stilettos. She looked stunning.

She smiled and stood in front of me and slowly turned in a full circle, allowing me admire her hot body. The stockings and heels made her legs look incredible, her ass I've already raved about, and the corset made her small breasts look bigger. The mocha-colored skin that I could see was flawless. She really was very beautiful.

Peaches sat beside me on the couch. I handed her drink to her and we clinked glasses and took a sip. "Excellent," she pronounced and turned to me.

"Money first, Mike," she said with a smile. "Need to make sure you didn't lose your wallet again."

I laughed and removed ten brand new $100 bills from my wallet that I had withdrawn from the bank the day before and handed them to her. Peaches folded the bills in half and slipped them down into her corset.

"So," she began, "in the last four weeks you have had sex with just about every girl I know, including three last week. You're currently the talk of the street."

"I guess you guys compare notes more than I thought," I said with a laugh.

She nodded. "We do. Actually, they've been talking about you for years. What's your story?"

"I just prefer prostitutes. Makes life less complicated," I replied.

"Expensive habit," Peaches stated and took a sip of her drink.

"It can be," I replied. "So what do the girls say about me?"

"That you've been coming around for years," Peaches said, "and you're always a perfect gentleman, you're never rough, you always tip well, and that you have a great body and a very nice cock which, and when you actually want more than just a bj, you really know how to use it."

"All that? I asked, wonderingly.

"Well, and the fact that you've been stalking me like a crazy man for the past several weeks!"

We talked for a few more minutes and finished our drinks. Peaches stood and held out her hand. I took it and stood up, and she led me to the bedroom. After closing the door she told me to remove my clothes, and stood watching while I did so. When I stood naked next to her bed she smiled at me and said "you certainly do have a nice cock!"

"What can I do for you, Mike?" she asked as she placed a finger on my upper chest and slid it slowly downward, letting it linger on my left nipple for a moment.

"Everything," I said, enjoying the heat of her fingertip as she slowly circled my nipple.

"Be a little more specific," she said with a laugh.

"I like to kiss and cuddle," I said. "Lots of touching and caressing. When I spend a lot of time with a girl I like to try and give her pleasure. I like giving oral as well as receiving it, and I like vaginal and anal intercourse."

"You sound like the perfect man," she whispered in her sexy voice, pressing her body against mine. "I'm going to let you give me lots of pleasure. First, though, lay on the bed on your stomach and I'll give you a massage."

I did as she instructed as she retrieved a few items from a night stand drawer and lined them up within easy reach on a shelf on the headboard. I saw a bottle of massage oil, a tube of Astroglide, and three butt plugs that ranged in size from small to very large. It was starting to look like I'd made a good investment.

Peaches joined me on the bed, straddling my upper thighs. "Great ass," she said as she reached for the massage oil.

Peaches squirted some oil into her palm and warmed it by rubbing her hands together, and then she leaned forward slightly and began kneading the muscles of my upper back. She had surprisingly strong fingers, and it felt wonderful as she worked the stress out of my knotted muscles. She gradually worked her way down my back, rubbing every inch of my skin. The oil was the warming variety, and as she rubbed it in it actually became warmer. I closed my eyes and enjoyed the pleasurable feelings she was giving me with her hands.

I lost track of time as the warm sensation flowed down my back. When she reached my lower back she applied additional oil and worked it in, rubbing both sides of my spine and my upper butt cheeks, gradually working down to my upper thighs. I sighed with pleasure as she ran an oiled finger down my butt crack and over my anus, and then back up again.

"How does that feel, Mike," she asked in a husky whisper as her fingers worked deep into my butt cheeks.

"Amazing," I replied.

Peaches spread my cheeks and ran her thumbs down my crack, one after the other. She pressed both thumbs gently into my perineum and rubbed slowly in gentle circles. Her knuckles brushed against my scrotum lightly and I could feel pre-cum oozing out of my cock. Peaches moved one thumb back to my butt crack and slid it up slowly until pausing with it pressing against my asshole. She continued to gently massage my perineum as she applied gentle pressure with the thumb pressing against my anus. The pleasure was overwhelming, and I moaned and said "That feels wonderful!"

Peaches applied more pressure and suddenly her thumb slipped into my asshole. I cried out and Peaches said, "Shhhh, just relax. Relax and enjoy."

I was very relaxed, but I hadn't had anything in my asshole since my ex-wife used to strap-on a dildo and butt fuck me. No matter how ready you think you are for that type of intimacy, there is still a little pain involved. It wasn't unpleasant though, and I didn't mind a bit when Peaches worked her thumb in deeper.

Pleasure was rippling up my spine as Peaches gently worked her entire thumb into my ass, still massaging my perineum with her other hand. My sphincter was rippling around her thumb and I told her it felt great. She worked her thumb around in my ass for several minutes and I loved it. I was leaking pre-cum into her bed sheets.

Peaches leaned forward and down and kissed me on the cheek and then the ear, and then retrieved the Astroglide and the smallest butt plug from the headboard. I tried to stay relaxed, but knowing she was going to stick that thing in my ass caused me to tense up a little. She whispered soothingly in my ear and reached forward with the hand that had been massaging my perineum and cupped my scrotum. She also re-inserted her thumb into my asshole and gently moved it around in a circular motion, and I once again relaxed.

I was disappointed when Peaches removed her thumb from my ass and let go of my balls. I could hear her applying the lube and rubbing it all over the butt plug. She reached down and spread my ass cheeks again and worked some lube into my asshole, and then I felt the end of the butt plug press up against my puckered hole. She pressed it forward firmly and it slid in easily. Fortunately the first one wasn't much bigger around than her thumb, but when the widest part stretched me before slipping all the way in, it burned a little.

Peaches reached back between my legs and once again cupped my balls with her oily left hand, rubbing gently as she worked the butt plug around inside my asshole. It felt absolutely amazing and I told her so.

"This is only the beginning, baby," she whispered in her sexy voice. Trust me; you're going to love this."

I was certainly loving it so far, and although it technically wasn't the anal intercourse I'd had in mind when I told her I liked it, who was I to complain?

Peaches worked the butt plug around in my ass for about 15 minutes while fondling my balls and cock with her other hand. When she removed the plug from my ass, I was disappointed. Peaches didn't waste much time getting the medium plug lubed and inserted into my ass though. My asshole spread wide as she gently eased the wide part past my sphincter and it hurt, but only for a few minutes. Then the waves of pleasure were rippling outward from my anus and through my entire body.

A half hour later she was working the large butt plug into my ass. It was huge - about five and half inches long and four inches in circumference. I didn't think she would be able to get it in me, but after several minutes of trying and lots of lube, I cried out as the wide part finally slipped past my sphincter and my asshole slammed shut around the base of the butt plug. Peaches whispered in my ear that I was doing great and she was so excited by my willingness to let her play with my ass.

Peaches stood and removed her panties but I couldn't see her because she did it behind me. She climbed back up on the bed and began working the huge butt plug around in my asshole. I was moaning softly as it massaged my prostate and I came a little into the bed sheets. I lost track of time, I was so immersed in the pleasure. However, far too soon Peaches was gently easing the massive butt plug out of my asshole. It hurt again, briefly, as the wide part spread me wide, but then the pain was gone and my sphincter rippled as it quickly readjusted.

Peaches moved forward with her legs still straddling my thighs. She spread my butt cheeks again and ran the tip of her index finger around the outer ring of my asshole. It felt so amazing I didn't want it to stop. She leaned forward and whispered, "Just one more thing for your tight ass, baby."

I hadn't seen anything else but assumed she had retrieved another toy from somewhere. She moved forward a little further, holding my ass cheeks spread wide, and I felt something warm and hard nudge against my asshole. I was so relaxed and well-prepared that I didn't even flinch when she gently but firmly moved her hips forward and inserted the item into my asshole. It slid in without pain, and she kept pressing forward, filling my asshole without the previous stretching of the butt plugs. It was warm and fit perfectly.

"That feels so fucking good, Peaches," I breathed, enjoying the waves of pleasure radiating outward from my asshole. "What is that?"

"This one is all me, sweetie," she purred in my ear. "I'm glad you like it."

At first I didn't comprehend what she was telling me. As she slowly eased back and then moved her hips forward it again, it began to dawn on me what she meant. A flood of emotion shot through me, but I didn't react physically, other than to continue enjoying the pleasure of the moment. I examined my feelings, first wondering why I didn't seem to be upset by what was happening to me.

First of all, it felt amazing. I hadn't had a real cock in my ass for over 20 years, since before I got married. It's not that I was opposed to the idea; I just hadn't actively wanted or sought to have sex with other men during that time. I think I mentioned earlier that I'd had a long gay relationship when I was in high school. Except for that relationship, all the gay sex I'd enjoyed previously had been by chance encounter. It was not something I ever planned and I wasn't usually sexually attracted to other males. For instance, with very few exceptions, I had never just looked at another man and thought that I wanted to fuck him, or be fucked by him. I didn't look at males on TV and think about having sex with them like I did females. There were a few exceptions, but not many.

Second, Peaches was at the very least a cross dresser, but far more likely she was a transsexual. She was far too beautiful to just be a man who dressed up in women's clothes, and her body looked - what little I had seen of it - far too feminine. She had obviously had some work done and it showed. I had viewed plenty of internet porn featuring sexy transsexuals and I had always found it to be a huge turn-on, but it had remained merely a fantasy and not one I had ever acted upon. I wasn't opposed to having sex with a cross dresser or transsexual; I had simply never acted on that particular fantasy.

Third, I was hugely attracted to Peaches from the minute I had first seen her perfect ass, even though it was completely covered. I had wanted to fuck her from the minute I set eyes on her, and nothing she had said or done to this point had changed that opinion.

Fourth, have I mentioned how amazing her cock felt in my ass? I couldn't have stopped her then no matter how I felt about the situation.

While all those thoughts raced through my head, Peaches had continued to fuck me. Her cock did not feel particularly large, and there was zero pain associated with what she was doing to me. In fact, the pleasure was nearly overwhelming. My cock was continuously oozing pre-cum. I didn't want her to stop no matter what.
"That feels incredible," I finally concluded out loud.

"Oh, baby," Peaches said in her husky voice, "I'm so glad you like it. Your tight ass feels so good!"

Peaches fucked me for the next several minutes and the pleasure just kept intensifying. She continued to whisper reassuringly in my ear, and then she picked up the pace and began breathing more heavily. She began grunting as she thrust her cock into my ass harder and harder as her balls slapped against my own.

"Ohhhhh, baby," she cried, "I'm coming!

Suddenly hot cum was flooding my insides. It felt wonderful, and I briefly wondered how I could have deprived myself of that intensity of pleasure for so long. Peaches' hot sperm jetted several times deep inside me, and I felt my own cum oozing out of my cock. I had a brief moment of panic when I realized she hadn't used a condom, but it was too late to worry about that right then.

When Peaches' stopped spurting, she lay forward onto my back with her cock still inside me. Her warmth covered me like a blanket, and she breathed heavily in my ear. Her shrinking cock finally eased out of my asshole and I felt a sense of loss that was almost physically painful that I had never experienced before. Finally Peaches rolled off of my back and I rolled up on my side to face her. I looked down at her flaccid cock which was still oozing cum, and reached down and gently touched it.

She smiled at me. "You never know how a guy is going to react when they find out," she said.

"That was pretty damn bold," I replied. "How did you know I wouldn't turn violent?"

"Because the word on the street is you're always a gentleman," she responded and kissed my lips lightly. "I figured even if you didn't want to continue when you realized, you wouldn't get violent."

"But this was much different. None of them were transsexuals."

Peaches looked into my eyes. "You're k**ding right?" she asked, her disbelief plain to hear. "Half the girls you've picked up in the past four weeks have been transsexuals. The ones who always insist on blowjobs? You seriously didn't know?"

I thought about that for a few moments and then laughed.

"Once you stuck your cock in me, I couldn't have stopped you if I tried," I said, running my hand down her hip. "It felt way to amazing."

"Thanks for giving me a chance, Mike," she said and kissed me again, this time darting her tongue forward into my mouth.

"You've got about four hours left," Peaches said a few minutes later. "What would you like to do next?"

Just then there was a soft tap on the door. Peaches smiled and called "Come in!"

The door opened and a tall blond with huge tits and a large bulge in her panties entered the room, smiling.

I looked at Peaches and she smiled and said "Say hello to Cream."

* * * * *

So, the good news is I am finally cured of my addiction to prostitutes. The only problem with that is now I am addicted to transsexual prostitutes. I scour the internet and magazines with personal advertisements, seeking transsexuals anywhere I can find them. I have traveled the world to have sex with some of the most beautiful transsexuals on the planet. I go to Brazil and Thailand three or four times a year to enjoy their richly deserved reputation as having the best, most beautiful, and most passable transsexuals in the world. What they definitely have is the "most." I spend more money on transsexual hookers than I ever spent on a cocaine habit I had back in the mid-80's.

My friends, if they realized the depths of my addiction, would most likely insist on some type of intervention if there is such a thing for my particular addiction. The only problems with that scenario - all my friends are prostitutes.