X-Rated Romp Through Life

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The business model that Jason and I came up with was one that was as old as time: There were women out there who needed sex but didn't have access to it for various reasons. We would provide that at a reasonable price and guarantee satisfaction or their money back. We advertised in ways that wouldn't raise the interest of the local vice unit. The best ads were via word of mouth. Satisfied customers had a way of wanting to share the good news.

I was surprised to find that most of our customers were married women in their thirties and forties with children at home and who were either in business or stay at home moms. My first encounter as a gigolo in the cities was with a woman of thirty-seven with two kids in school and a husband who was successful at his business. Her name was a secret, but she let it be known that I should call her Jaqueline.

Jaqueline arrived at the hotel room that I rented for the occasion with a harried look about her. She said that she had to pick up her kids in about two hours. She wanted to just get undressed, lay down and get fucked, end of story.

"Jaqueline, I'm afraid that that's not how it's going to be. I don't do the bunny routine. You paid for sex with me and I plan to give you sex, but sex that you will remember."

With that I took her bag from her hand and put it on the luggage rack at the foot of the bed. Then I turned and took her in my arms and just held her for a while, running my hands up and down her back then down to her ass. She was in great shape. She said he was a runner.Then I put one of my hands between us and ran it up and over her breasts, her great breasts. I thought at that point that I should be paying her. My cock was responding to the tactile exercise and was pushing against her crotch. I couldn't help but wonder why she didn't pick some guy up in the produce section of a super market or on a run along the river parkway.

I decided that I should wear pants that were loose and thin to make the best visual impact on the customer; it was working. As I slowly ground my cock into her crotch, I also started to work on getting her out of her clothes. She was wearing a loose and very thin summer dress that had a zipper in back running to the crack of her ass. I worked the zipper down to where I could feel her panties.

We were standing in front of a large wall mirror which gave me a view of her back. It was tanned and firm. Her panties were black and low waisted. Her bra appeared to match. I reached up and pulled the dress from her shoulders. She lowered her arms and the dress fell to the floor. She was now in just bra and panties. They matched very nicely and may have been bought for her wedding night.

With my crotch still working at hers , she looked up at me and said, "Will you get undressed so I can see that thing that's been trying to get at my cunt?"

My goodness, this was no princess. She knew what to call her vital parts when the time was right.

Before I got undressed I released the clasp on her bra and let it fall on her dress. Her breasts were magnificent. I cupped them both and my cock achieved new proportions. Then I stepped back and started to undress. When I reached my silk boxers, my cock snaked out of the opening and into her view.

"Yes, that's what I want."

She grabbed my cock in one hand and sank to her knees. She put my cock in her mouth and began to give me the blowjob of a lifetime. Here I was being paid by this woman to attend to her sexual needs and she was blowing me. I didn't want to come, so I told her to stop so I could fuck her in any way she wished. She wished to continue blowing me. Then I came in her mouth.

Fuck, what a blow job. Could I accept money from her? I would have to reciprocate. I could get it up for a good fuck, or I could eat her.

"You have no idea how that turns me on," she said. "My husband won't let me blow him. He thinks it's dirty. If he only knew how I get off doing it."

She had swallowed all of my semen and was licking her lips as she stood and hugged me. I reached down and put a hand into her panties. Her cunt was sopping and smooth, almost hairless. I inserted a finger into her and tried to find her G-Spot. I instead found that her clitoris was huge and waiting to be massaged. I guided her to the bed and laid her back so her legs were hanging over the edge. I pulled her panties off and got to work on her clitoris that screamed for attention.With two of my fingers working at her G-Spot and my mouth sucking at her clitoris, Jacqueline came so hard that she nearly blacked out and almost suffocated me.

During cunnilingus, my cock had come to life and was looking for a handy cunt. As she lay there recovering from her major orgasm, I got up, put on a condom, got over her and slid into her very open cunt. When I reached bottom, she opened her eyes and smiled. "You sure know how to fuck, don't you?"

"Yes, I know what turns me on, so I just assumed that it turns women on as well." Then I began to slam into her as hard as a had ever done with any woman. I knew by then that Jacqueline was into being fucked, not made love to.

At the end of the session, Jacqueline took a quick shower. She paid me and gave me a very generous tip. I told her that I should be paying her since she was the best piece of ass I had ever experienced. She patted my cock one more time, then left. I was in love all over again, and I had another $300 to add to the bank account.

The next two years were filled with more of the same. There were all manner of woman who called up us for relief from their ho-hum or nonexistant sex lives. I fucked the heads of major companies, military officers, politicians, church women and just your average mom who wanted to experience what they read about in the romance novels they read. Life was good and the money was better.

As we progressed, Jason and I added a few other guys to the stable. They were mostly students, but one was a cop and another a construction worker. The cop really turned women on, and they showed it by making return visits. At the five year anniversary, Jason and I were rich beyond our imaginations.

I didn't waste my money on frivolities except for a very expensive gym where I worked on keeping myself in shape. There was, of course, the need for a car that would attract the ladies that I didn't get paid by for sex. And there was a nice place on the river that I called home. But the rest went into investments and improving the business.

We never needed to call our attorney for legal representation. But since she was on retainer at no expense to us, I made a call on her at least once a month to make good on our agreement. She appreciated it; so did I.  

Epilogue

Life for me was one that other men and most women can only dream of. With the advent of sex enhancing drugs, I continue what I started. In many respects, the ED drugs make sex better because erections have no end if that's what you want. With age comes a realization that the older we get, the more we appreciate sex. That seems to go double for women.There is nothing I like more than an older woman who has no worries about pregnancy or a youngster walking in on us. But I've always had a thing about older women, starting with Betty, may she rest in peace.

Then there's the apparent attraction that younger woman have for older guys with graying hair. Among my favorite liasons are high school and college students. They must enjoy fucking older guys as much as I liked fucking the Mrs. Bangors of the world when I was their age. Then there's the older female police officer who stopped me for no apparent reason one day. But that's anothet story for another day.

Word got around my old neighborhood and the town where I went to school that I was a great teacher in all matters involving sex. Some of the women I had kept well fucked over the years now introduced their daughters to me, and, in one case, a granddaughter, for their first sexual encounters. They all seemed to benefit from it, me included.

Without a doubt, the best experience with a young woman involved the youngest daughter of the pastor. Cheri, the pastor's wife, was still one of the women I visited when I returned to town. She had retained her figure and love of cock. She thought that her daughter would benefit from the teachings of an older man; I agreed.

Wanda was eighteen when Cheri introduced us. She had been a surprise pregnancy to both Cheri and the pastor. Cheri said that she couldn't be sure who her father was. We met at a restaurant in town, the same one where I had been with some of the other women in my life. Wanda was your average eighteen year-old female. She was neither gorgeous nor ugly. Her body was well constructed, however. Cheri told me earlier that Wanda was suffering from self doubt.

It was agreed that we should take a room at one of the local motor inns. Cheri would rent it by phone then drive there alone. Wanda and I would go in my car, a new Corvette.

While enroute to the motor inn, I laid a hand on Wanda's left knee, now exposed. I didn't get any resistance, so I continued up her leg. As I neared her crotch, Wanda spread her legs and slid further down in the seat. She wasn't wearing panties.

"Are you sure that you've never had sex before?" I asked.

"Only with about half of the football team and all of the basketball team."

"Why is it you want to have sex with an old guy like me?"

"Because I've heard my mom talk about you and your cock. I want to feel what she feels. Besides, young guys just put it in and come. I want to be truly fucked for a change."

I slid a finger into her cunt as I drove. Thankfully, the Corvette had an automatic transmission. When we stopped at the last red light before reaching the motor inn, Wanda was very near an orgasm. A four by four truck drove up along side as I fingered fucked Wanda. The driver, a youngish man, looked over and saw what was happening. When the light changed, the pickup stayed alongside us as I worked at Wanda's cunt. I was amazed that he was able to keep his pickup on the road while trying to get his cock out of his pants.

When we pulled into the motor inn, Wanda was hyperventilating which meant to me that she was about to come. Then she did. I stopped and worked another finger into her as she panted and rolled eyes.

"Oh fuck," was all that she could come up with as I kept working at her cunt.

"Maybe we should go in now," I said.

"OK."

We went to the room that Cheri had rented for us. It was in the back where we were less likely to be seen going in. Cheri was in the room when we entered. Her smile meant one thing to me: she expected to get a piece of me as well.

"Wanda, why don't you get undressed for Bill?"

Wanda didn't waste any time pulling her dress over her head. There she stood in only her bra. Cheri seemed a little surprised that she wasn't wearing panties. Then Wanda took her bra off, exposing her very firm and very beautiful breasts. They were similar to Cheri's breasts on that first day I fucked her in the church office.

I had already had my finger in Wanda's cunt, so I now felt OK about going to her and fondling the rest of her.

"By the way, Cheri, did you know that Wanda isn't exactly a virgin?"

"I know that she's been fucking a lot of the boys in school, but she hasn't been 'really' fucked yet. Besides, I've been fucking a few of the guys she's fucked. If you recall, I like young guys."

"I'll bet they appreciate that. How do you contact them for sex?"

"Wanda is my recruiter. She brings one or two of them over for a visit from time to time. The purpose isn't made clear to them until I start my touchy feely routine. The last time was with two guys who came over thinking that they were going to help Wanda with some stuff. I wore a white T-shirt, no bra and very short shorts. It was by complete accident that I spilled some water down my front. When my T-shirt became translucent, both guys couldn't take their eyes off me. When Wanda walked out of the room to give me the prearranged opportunity to come on to them, I told them that since they had already seen me, I would take off my shirt if they would do the same. When I pulled my shirt over my head, they were both speed undressing. They didn't stop at their shirts. Both took off their pants. Their cocks were standing out of the holes in their briefs. I invited them to touch me. Both grabbed a breast while I grabbed their cocks and began to jack them off." By this point in her story, my cock was standing out like it did when I was eighteen. The Viagra that I had taken earlier was helping the process. I took off my pants and shirt. My cock found its way out of the hole in my boxers. Wanda stepped up and took my cock in hand. "I didn't want to waste their hard cocks by bringing them to orgasm outside my cunt, so I let them go and removed the rest of my clothes. I wasn't as fit as I was when you first fucked me, but they seemed to be impressed if the iron-like rigidity of their cocks was any indication. I told one of them to lay on the floor. I got down on all fours and took his cock in my mouth. I motioned for the other to get behind me and put his cock in my cunt from behind. It took no time before we were all three being satisfied. I don't think the one I was blowing had ever experienced the act before. It took less than a minute for him to come. I was able to swallow all of his semen as the one behind me shot into me. It was a truly great experience. Before the day was over, the boys had fucked both Wanda and me several times. They and some of their friends stop by from time to time to service my needs. Now, how about you get to the business at hand." Wanda sank to her knees in front of me and took my cock in her mouth. She clearly had gained from her mother's instructions. I wouldn't let her bring me to orgasm, however. I wanted to put my cock into that young, firm cunt. Wanda was as anxious for me to get into her as I was. She lay back on the bed and spread her legs. Cheri went to one of the chairs and undressed, then sat down. I slid up onto Wanda, my cock trailing the length of her legs until I reached her cunt. It was so wet and open that I was able to slide in with no help. As I settled into her as deep as I could go, she grabbed my ass and tried to get me deeper. Then I began to slide in and out, increasing force with each stroke. She was enjoying the slamming, however, because she came about half way into the process. Then I pulled out to the point where just the head of my cock was at the entrance to her cunt. I them worked back and forth on it until she began to pull on my ass once aagin to get me back into her. When I began to once again slam into her, I looked at Cheri and saw that she was enjoying the show. She was sitting on the chair, legs spread and a finger in her cunt. Her face was flushed. Them she came. The scene was so sexually charged that I came along with Cheri. Wanda, too, pounded up into me as she came. I lay on Wanda, my cock softening inside her. "Oh my god, that was the first time I've come with a man's cock in me." "The next time, try a blow job first. The guy will last longer if he has come once. Just make sure he doesn't go to sleep after you blow him." We spent the rest of the day in the room. I put the Viagra to good use fucking both Wanda and Cheri several times. Fucking mother and daughter at the same time is an experience that every man should have at some time in his life.

When we left the motor inn, it was dark. We decided to go to my favorite café for dinner. When we walked in, I saw an old friend eating with her husband. It was Mrs. Bangor. Her face lit up, then she got a look of concern when she realized that the two women were with me. I walked to where they were sitting and greeted them. She said that she would like to get together before I left town. Her husband smiled and said that he would be traveling the next day, so we should meet then. We agreed to meet at her house.

It was like old home week. We reminisced about old times and our sex lives. She hadn't slowed in her search of new partners. She said that her husband was retired, but he knew about us and went out of his way to accommodate her insatiable need for sex outside of their marriage. His "travel" was to the golf course. We ended the day with a pill and a lot of sex.

Life goes on. I haven't married, nor have I had any desire to. Compiling a history of all the women I have had sex with is virtually impossible. This autobiography would be long beyond belief if I enumerated them all, but they were all good in their own way. Some were magnificent, some were outstanding, all were good.

When I visited my mother in the nursing home where she died, I found that sex between residents was rampant, so even there sex was king. One can only hope.

A Conclusion, but Not the End, Fuck On!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
1 Comments
AnonymousAnonymousover 12 years ago
oh boy!

Never before have I been guilty of the sin of envy but now guilty as sin!

Share this Story

Similar Stories

My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
A Gift From His Father Ch. 01 A young man receives a strange gift with unique powers.in Mind Control
Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
A Blizzard & the Night of Firsts A storm forces a virgin to find warmth with 3 women.in First Time
That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
More Stories