Peaches and Cream

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.