Jenny and I-3

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Jenny and I-3I had plenty of time to rest and eat some lunch before Jenny showed up from work. She was a little bit tired, so we sat on the sofa in the family room to talk for a few minutes while she rested. For no reason other than just making conversation, I told her what had happened at Mrs. Jackson’s house that morning. With practically anybody else, I would have been better off keeping my mouth shut about Mrs. Jackson and the fucking episode.However, Jenny and I had always shared our secrets. I guess I had conveniently forgotten that Jenny had not told me about her fucking sessions before we started. I had to find out about those on my own, but it never bothered me. As it turned out, Jenny was not upset that I had fucked another woman, but she was very interested in the $100 tip that I had received.”Dammit, Billy, I told you that you had a woman’s dream between your legs. How do you feel about selling sex? You know, you could make a lot of money as a gigolo. Just think about those guys on the TV show that we’ve been watching. They talk about getting as much as several thousand dollars for a single date. I know that you could not make that much in this town for a single date, but, at your age, $50-$250 per date would not be bad. What do you think?””Oh, my God, Jenny, that would be a great way to make a living! Shit, I’d love to give it a try, but how would you feel?””I don’t know for sure, Billy. I think I would be fine with it as long as you were getting paid. If you did it for free with another woman, I would probably get jealous, but I don’t think a paying proposition would bother me in the least. Especially, if you let me be your agent. You could pick up the stray woman as you cut grass and probably do pretty well. On the other hand, I’ll bet that I could drum up you a steady client list from the girls that come to the beauty salon where I work. Most of them would be high school girls who would be thrilled to be fucked by a professional. It sounds like great fun to me.”We talked about it some more and worked up a few ground rules. The two main rules were that the girls had to prove they were free from disease and they were protected from getting pregnant. They had to know, upfront, that I had no intention of marrying them or supporting a k** that was produced by our meeting. We figured that the best bet for our meeting would be at the girl’s house. That way, if we were caught in the act, it would be apparent that the girl had made the arrangement.Jenny said that she would start working on the deal tomorrow, but first, she was going to work up a form for the girl to sign to prove that she had solicited me, and not vice versa. I didn’t think the paper would do much good if I got arrested, but it made Jenny happy so I went along with the deal. I was young enough to figure that I was going to live forever, so I was not worried about getting caught.Once we had that thrashed out, Jenny and I adjourned to her bedroom. We normally fucked in some variation of the missionary position, but Jenny thought it would be a good idea for me to practice some of the other positions in case my customers wanted to give them a try. This time, she selected the doggie position. That was not my favorite position, but I went along with Jenny because she thought it was important.I didn’t like the doggie position because it was impossible for me to bump my partner’s clit while we were fucking, and both Jenny and Mrs. Jackson had seemed to like that little extra something. I hope to come up with an alternative to the clit bumping, but I didn’t know what it would be at the moment.Nowadays, no foreplay was necessary with Jenny. She would start to drip from her cunt as soon as we started to walk toward her bedroom. Therefore, it was only necessary for us to remove each other’s clothes, and to climb onto the bed. Hell, I didn’t need the foreplay, because I was always ready to fuck!Previously, when we used the doggie position, Jenny had always rested on her hands and knees. This time, she proposed that she rest on her shoulders and use a pillow for support. As soon as she assumed the position, I knew that I preferred this version because it made her cunt easier to get to.I climbed on the bed and knee-walked up to Jenny’s ass. I was already sticking straight out, so it was easy to slide my cock back and forth along Jenny’s pussy slit. I got myself good and wet and lined up with her pussy hole. By this time, Jenny’s cunt was loose enough for me to slide right in. I kind of missed having to work myself past those first muscles and stroking several times before I could bottom out, but I chalked this up to just one of those things.I began a steady stroking rate, but there was something wrong. Jenny realized the problem first: I was not hitting her G-spot. I shifted position, and she tightened up a little more, and that combination put me in the right place. Neither one of us were really fans of the doggie position, and that problem with not hitting the G-spot was the reason.I was about to come, but Jenny was still not ready. This was a totally unacceptable situation as far as I was concerned, so I wracked my brain for a solution to the problem. Suddenly, it dawned on me that all I had to do was reach around her thigh and diddle her clit with my fingers. I hardly had to touch her clit before she started coming. That triggered my release, so that, for practical purposes, we came together.Both of us were happy that we had a solution to the problem, but it didn’t do anything to increase our interest in the doggie position. Oh, well, I had a solution to an aggravating problem if the question came up. But honestly, I hoped that I would never be asked to perform in the doggie position. Unfortunately, we didn’t have time for another fuck that afternoon, but Jenny had been relieved, and I always considered any fuck as a good fuck. Anyway, we were showered and dressed before our parents got home.I now had an unexpected $100 that I had to deal with. I could not open a bank account on my own because any banking account for a person under 18 in our state required that a legal adult also be on the account. I did not want my parents to know about my new job, and they were the only adults I knew of to sign up with me. Until Jenny turned 18, it looks like the only choice I had was to hide the money. The only solution I could come up with at the moment was to stick the money between the pages of a book that I normally kept in my room. I hoped that was going to be good enough, but I hated to bet on it.A few days later, Jenny had a customer for me. She was a high school senior who just could not connect with a boy. The girl had a serious acne problem that made her almost hideous to look at. She could cover most of her problem with heavy makeup, but that made her look like a tart. Despite all of this, she was a very nice and intelligent girl who was just stuck with the worst sort of luck. Alice Holbein was her name, and she was paying me $250 for the full treatment, including dinner and a movie. Thank God, she had a car so that we did not need a hotel room.Fortunately, I did look several years older than my actual chronological age, so Alice did not have to be embarrassed to be seen with such a young boy. Of course, there was no alcohol involved, her parents insisted on that, but we went to a very nice Italian restaurant and then to a movie. After the movie, Alice drove us to one of the common high school make out spots. I had never been there, and Alice had not been there in some time, so this amounted to a new experience for both of us.Like any sensible teens, we moved to the back seat before we did ödemiş escort anything else. The weather was still quite warm, so that we were wearing light clothes without coats. That made things a lot easier, and Alice had pitched a couple of towels on the backseat of the car before she left home.The first thing I did was to open my attack with a kiss. I wanted to work slowly, so this first kiss was kind of generic and not a French kiss. I don’t know if Alice was disappointed, but a couple of more kisses resulted in her pushing her tongue into my mouth. Okay, I know when I’m being hinted at, so I went into full French kissing mode. Jenny had been a great teacher, and I prided myself on the quality of my kisses. Therefore, Alice was breathless in a very few minutes.When we paused in the kissing, Alice grabbed my left hand and pushed it against her right tit. Her breasts were of average size, so there was a handful there for me to work with. I could feel her hard nipple pressing through her bra and blouse into the palm of my hand. I resumed my kissing attack, but directed it toward her earlobes. This caught Alice by surprise, but she seemed pleased, especially when I began to massage her breasts and rub the palm of my hand around on her nipple.I kept up this activity for a few minutes, but I didn’t want to waste too much time on this stage of the date. I used my right hand to unbutton her blouse all the way from her neck line to her waist. Without further ado, I used both hands to remove her blouse and her bra. She responded by removing my shirt and exposing my bare chest. I had followed Jenny’s advice and not worn any underwear.Alice pulled me to her so that my chest pressed on hers and I returned to kissing her lips, mostly with French kisses. After a little bit of that, I pulled away from her and began to play with both tits. I massaged a tit and played with the nipple while I sucked and nibbled on the other nipple. I made a point of switching back and forth so that I would not make either one of them sore. I gently pushed her back so that she was lying on the car seat.By this time, Alice was so aroused that she was pulling at my belt to try to get it loose. I obliged by kicking my shoes off and sliding my pants completely off. I guess a bystander would have found it hilarious to see me dressed only in a pair of black socks.I flipped up her skirt and pulled her panties off along with her shoes. Thank God, she was not wearing pantyhose. Her panties were so wet that I took the time to loosen her waistband and pull her skirt off; there was no point in getting liquid all over her skirt. I worked a towel under her ass to help protect the seat. It looked like she was going to pour out a lot of liquid before this experience was finished.Alice was now wearing nothing but her stockings, and I was secretly amused that we were dressed so nearly alike. As was common high school girls, her pussy was completely clean of hair. Since there was no hair and she smelled so clean, I decided to give her a treat; namely, a little cunnilingus. I could tell she was not expecting that, but she certainly did not object as I started licking her pussy. Only the first stroke on my tongue was enough to start her panting and moaning.I did not keep this up for very long because I did not want to spoil the effect of the fucking. I sucked for only a moment on her clit, but that seemed to be enough to set off a minor orgasm. Of course, my cock was as hard as it ever got, so I was ready when I lined up with her pussy hole. There was no problem finding it. I rubbed my cock against her pussy slit to pick up as much lubricant as possible.Oh, my God, nobody had told me that Alice was a virgin. This was my first experience with a hymen, and I hope I didn’t screw up! I said, “Alice, I just discovered that you are a virgin. Are you sure that you want me to break your cherry?””Certainly! This has to happen if I am to get everything that I want. Go ahead and break it. Just give me a moment to absorb the pain.”Well, if that was what she wanted, she was going to get it. She had certainly paid for it. I pushed gently past her pussy lips and felt the membrane stretch. Alice moaned very quietly, and I continue to push. Suddenly, I felt her membrane rupture, and Alice squealed as if she had been pinched. I stopped immediately and waited to hear what she had to say.”I was surprised. It didn’t hurt nearly as much as I expected, and I am ready for you to continue.”That was all I needed to hear, and I worked my way down her tunnel until I was stopped when my pubic bone pressed against her clit. Alice enjoyed the contact as expressed by a sincere moan of delight. She was as tight as I expected, so I waited a few seconds to give her a chance to adapt to my size. Alice got tired of waiting and told me to get busy. That’s what I wanted to hear, so I began to stroke slowly at first to give her a chance to get used to me and my movement. However, after a few strokes I did speed up, and she definitely started to enjoy the fuck.There was no question that I was rubbing her G-spot, so I figured this would not last very long. As I expected, Alice quickly begin to pant and moan in pleasure. I was just beginning to feel the rise of my jizz as she began to show the signs of a beginning orgasm. She tightened her pussy muscles and began to moan rather loudly. As was always best, she and I got into sync and we came at the same time. I am sure that she could feel my jizz jet into her as I came, at least I hoped so.We took a few minutes to rest from our adventure before we got dressed. Of course, Alice had begun to pour juices out of her cunt as soon as I pulled out my cock, which was acting as a stopper. She looked at me with an embarrassed grin and thanked me for removing her skirt before it got damaged from all the drippings. I smiled back, and there was no question that we were friends.Alice took me home, and all the way, she kept thanking me for the wonderful time she’d had. She also wanted to know if she could hire me again. Of course, I was so flattered by that question that I could hardly speak. I assured her that I would be delighted to date her again. All she had to do was to make the arrangements with Jenny. As I kissed her good night, I realized that after the first three or four minutes of the date that I had not thought any about her acne problem. It looked like the guys at the high school were even dumber than I thought to leave her sitting on the shelf like that.My parents knew that I had been out on a date with a girl from the high school. What they didn’t know was that she was paying me for my time. Therefore, they didn’t worry about it, and just were glad that I had started dating, a topic they had been concerned about for a few months.On the other hand, Jenny knew exactly what I had been up to. As soon as I want to my bedroom to change clothes, Jenny showed up for a run down on the date. I gave her all of the details that I could remember, and she managed to cross examine a little more information from me. She also gave me $225 after pulling out her 10% commission. This was another one of those things where, if Jenny was happy, I was happy.I was in a hurry to get to bed because I had a lawn care client scheduled for tomorrow morning. This was a different woman from Mrs. Jackson, so I did not know whether or not I would just cut her grass or would also fuck her. Either one was acceptable, though, naturally, I would prefer to throw in the fuck. Not only did I like the prospect of fucking, but I would like to receive the extra money.Speaking of money, I stuffed my recently earned $225 into a book. God ödemiş escort bayan help me if Mom stumbled across that much money. She was even better at cross examination than Jenny, so I knew that I would wind up telling all to her, and I knew that would put me into such deep shit that I would be grounded for life!I left for Mrs. Jane Thornton’s home without much realistic expectation of being fucked, but I could always hope. Mrs. Thornton was a “woman of color” (African-American) with every intent of making sure that every person, especially the Whites, accorded her every bit of the respect she believed that she deserved. Thus, I felt that I was walking on eggs every time I went to work on her yard. Were it not for the fact that she paid me $30 instead of the $20 that most of my customers usually paid, I would have stopped working for her. As it was, I figured that the 50% increase that I charged Mrs. Thornton barely paid me for the aggravation of working for her.I went to her backdoor: being a servant prevented me from using her front door or porch. Thus, I was pissed off before I even knocked on the door. It took four knocks before Mrs. Thornton deigned to show up at the door. She opened the door to the limit allowed by the chain lock and said through this small opening in an imperious voice, “Who are you, and what do you want?”That was step two toward pissing me off. I knew that Mrs. Thornton knew damned well who I was, and she was just working on her superiority kick. I said, “Good morning, Mrs. Thornton. I’m Billy Weston, and I’m here to cut your grass.””Well, Billy Weston, why are you standing at my backdoor and not cutting the grass?””Because, Mrs. Thornton, you have to give me the key so that I can get the lawnmower from the tool shed.””Very well, but you stand there where I can keep an eye on you while I fetch the key.”This time, I didn’t say anything but I stood there and fumed while the old bitch fetched the key. This was step three toward pissing me off. I had promised myself that I would allow Mrs. Thornton only five insults or aggravations on this day. One more, and I was leaving her in the lurch.”Here is the key, but you be sure to return it to me as soon as you open the door to remove the lawnmower.”Okay, that was number five. I said, “You can keep the key, Mrs. Thornton! I just quit cutting your grass. You can find somebody else for all I care, or you can let the grass grow. I could not care less! I have had all of your insults and putdowns that I can stand. So long, Mrs. Thornton, and to hell with you and your lawn.” I turned around and stalked off toward home.Mrs. Thornton was thoroughly confused. This was first time any White person had ever dared to talk to her like that. She began to fume and shout, “YOU HONKY, YOU GET BACK HERE AND APOLOGIZE TO ME RIGHT AWAY!” I gave her the one finger salute and walked away. I couldn’t help grinning to myself when I was sure Mrs. Thornton couldn’t see me. I felt that my revenge on Mrs. Thornton was complete, and there was nothing else I needed to do.I was nearly home when I heard a voice calling to me. “BILLY WESTON, ARE YOU TOO BUSY TO HELP ME WITH A PROBLEM THIS MORNING?”I turned to see who was calling me, and it was Mrs. Jackson, currently my favorite customer. I walked over to where she was standing on her front porch. “Sure, I can help you, Mrs. Jackson. What do you need for me to do?””Come into the house, and I will show you.” I followed her into the house, and Mrs. Jackson closed and locked the front door. What the hell was going on? Mrs. Jackson beckoned to me to follow her. She led me into her bedroom and turned to say, “Billy, I need help from you like you provided me the other day.” I stared at Mrs. Jackson uncomprehendingly, but I suddenly understood what she meant when she opened her housecoat, and dropped it on the floor.Mrs. Jackson was completely naked now, and I had no doubts about what she wanted from me. I did some quick calculations in my head and said, “Okay, Mrs. Jackson. I understand what you want, but you must understand what I want. I am trying to earn enough money to buy a used car, so I have decided to become a professional gigolo. I feel that I must charge you $200 for my services. If that is agreeable, please give me the money and I will do everything I can for you.”Ruth Jackson was somewhat taken aback by my blunt statements. Nevertheless, she felt she was in great need of my unique services. I was the only man who had ever seemed to care about making sure that she enjoyed sex, and she would do almost anything to keep me servicing her. She said, “Very well, Billy, but for that price I want something more than what you gave me the last time.””For $200, you can call the shots. Just tell me what you want me to do.””Okay, Billy. Strip off those clothes and take a quick shower.” I was gone only a shade more than 10 minutes before I was back and standing naked waiting for her next order. While I was gone, Ruth Jackson had fetched $200 from her purse. She gave the money to me, and I stuffed it into the pocket of my shorts.”Billy, I want to start off with a round of cunnilingus. Do you know how to do that?””Oh, yes, I can do that, but can I make a suggestion?” Ruth nodded, and I said, “You will enjoy it a whole lot better, and so will I, if you shave off your pussy hair first. How do you feel about that?””That sounds like a great idea to me, but you will have to do the actual shaving. My husband has an electric razor. Can we use that?””Yeah, that sounds like a good idea. Please get the razor because it will take you a hell of a lot less time than it will me if I have to find it.””Okay, that’s easy enough. His razor is in the bathroom that you just used for your shower. Let’s move in there, and you can get to work.”We went into the bathroom, and Ruth handed me an electric razor and the pre-electric shaving lotion. I had Ruth lean back against the sink and spread her legs. I put some of the shaving lotion in my hand and rubbed it in the hair on her pussy. Ruth squealed and said, “That damned stuff is cold!”I chuckled and said, “Yeah, it is cold, especially if you use it on a new place.” I clicked on the razor (it was battery-powered) and begin to work on Ruth’s bush. It was a luxuriant mass of hair, and I actually stalled the razor a couple of times. Eventually, I managed to remove all the hair I could reach from her front. I had Ruth turn around and bend over so that I could get the hair most easily reached from her rear. While I was about it, I shaved up around her ass hole. It took a lot longer to do a decent job than I had expected, but finally Ruth was as clear of hair around her pussy as any high school girl. Ruth and I heaved a sigh of relief: at last we were ready to get to the sex part.We ignored the mess we had made and left to return to the bed. Ruth picked up a couple of towels on her way.Ruth lay on her back on the bed and spread her legs. I got between her legs and quickly discovered that this just wasn’t going to work. I got a pillow to put under her ass, and that fixed the problem for cunnilingus. I wasn’t so sure about fucking with the pillow there, but I would worry about that later. Dammit, my first lick against her pussy lips really stung my tongue: I should have had her wash off the pre-shave before we return to the bed. Well, I guess this was a case of a beginner’s mistake. I excused myself long enough to grab a damp washcloth to wipe off her pussy before I tried eating her again.Ah, that fixed the problem! Well, I promised myself that I would never make that mistake again. Just as Jenny had taught me, I licked firmly enough to make sure escort ödemiş that she felt the motion of my tongue. After a few simple licks, I began to work my tongue between her outer lips, and to put pressure on her inner lips. Ruth was having trouble keeping still under the influence of this stimulation. She had also started to moan as I licked her.Ruth rose higher and higher toward an orgasm as I worked on her pussy, and she seemed to reach a point where she was hung on the verge of an orgasm, but couldn’t quite get over the mountain peak. I had a sudden inspiration: the next time my lips reached the level of her clit, I switched from licking to sucking. I grasped her clit with my lips and applied as much vacuum as possible. That was the added stimulus that Ruth needed. She exploded into a violent orgasm and jerked her hips up off the pillow so hard that she banged my nose. For a moment, it hurt so much that I thought my nose was broken. Thank God, that was a false alarm.During the course of this orgasm, Ruth was bouncing her hips around and about so much that I was totally unable to resume contact with her pussy. I had no choice but to let her run dry. She finally ran down and simply collapsed on to the bed and the pillow. I couldn’t tell if she was asleep or u*********s from fainting, but Ruth seemed to be in good condition so I just let her lie there.Ruth’s u*********s spell lasted only a few moments, and, frankly, I was relieved at that. The next thing I knew, she had grabbed both my ears in her hands and had pulled me up far enough for a deep kiss. I guessed that meant that I had met her expectations, possibly even exceeded them.Ruth was still somewhat disoriented from that overwhelming orgasm, so she rolled off the pillow and pulled me down to cuddle with her. She stayed like that for over 10 minutes without saying anything, and I wondered what was going on in that befuddled mind of hers. It had been my limited experience that an extreme orgasm could interfere with one’s thinking for a short while.She grabbed me in a tight hug and announced, “Now I want you to fuck me.”Fortunately, there was no fumbling around this time. I pitched the pillow out of the way, and Ruth rolled onto her back. I moved between her legs and put her ankles on my shoulders. I had seen that named the “butterfly position” in a couple of the websites that I had researched. It seemed like an adequate name to me, so that was what I stayed with. Anyway, now her pussy was pointed toward the ceiling, and I had no trouble reaching her hole with my cock head.Needless to say, the cunnilingus had made any other foreplay totally unnecessary, so I was able to slide my cock past her initial pussy muscles and into her tunnel. Only a couple of strokes let me bottom out: I bumped very nicely against her clit, and produced a delighted little squeal. As before, there was no problem with me delving as far as I could reach into her cunt. Also, Ruth was still tight enough that I had no problem maintaining pressure against her G-spot.Yes, this was what Ruth really wanted. That exercise in cunnilingus was just a little bit of revenge on her part for my cheekiness in demanding a $200 fee for servicing her. Well, I really didn’t care all that much: I was already into the successful businessman’s mode of doing anything reasonable to keep the customer happy.I began to stroke, and Ruth began to moan, so I knew I was doing it right. I simply stroked into her at a steady rapid rate, and she rose higher and higher toward another orgasm. I felt mine rising, too. Eventually, we ran into a situation similar to what we had faced during cunnilingus. Namely, Ruth was hung at the lip of her precipice, but just could not cross over the brink. I felt that, so I started pumping a little harder, and that caused me to spurt my first jet of jizz.The feeling of my semen striking the wall near her cervix triggered her orgasm as I had hoped. I guess that she had been hung on the lip of an orgasm for long enough for her nervous system to be stretched to its limit. For whatever reason, there might have been, she had another one of those earthshaking climaxes very similar to the one she had the previous time I fucked her.She fell into a deep faint or sleep, but she did not appear to be in any distress, so I did not worry about her condition. It was already past lunchtime and my stomach was getting angry with me, so I cleaned myself off and got dressed. I figured that that was all of the sex that Mrs. Ruth Jackson would be able to handle for the rest of the day. I already had my money from her, so I let myself out of the house and went home to fix some lunch.Jenny was due home before long, so I showered after lunch and put on some shorts and a T-shirt. I watched a show on Military Channel while I waited for Jenny to show up. She waltzed in with a very happy look on her face, so I knew that she had some good news to match mine. Jenny had me tell my story first, and she laughed when she saw the $200 that I exhibited.Jenny’s news confused me a little bit in that I thought of it as a mixed blessing. It turned out that my next customer that she had found for me was the daughter of the local police chief! The girl was willing to pay $250 for the same kind of treatment that I had given Alice Holbein. I was thrilled by everything but the part about the girl being the daughter of the police chief. That scared me because I thought it meant that we were pushing the safety envelope a little too hard.Jenny explained that the situation was exactly the opposite. She had a paper signed by Janice Upton proving that she had solicited me for sex. Therefore, if the police gave me a hard time or tried to arrest me, I could use the form Janice had signed in my defense. Jenny was certain that the police chief would not want his daughter to be embarrassed in open court, so he would squelch a simple prostitution charge. Jenny felt that this would be great insurance, and she hoped to recruit the daughters of the district attorney and the mayor as my clients.I had to agree that Jenny’s plan was just devious enough that it might work. Anyway, I couldn’t find any basic flaws in the plan, so I went along with it. My date with Janice Upton was scheduled for tonight, so Jenny decided to put off our afternoon fuck to give me plenty of time to rest up for Janice. I thought she was being unduly cautious, but, as usual, I went along with Jenny in things having to do with sex.Mom and Dad were surprised when they got home and saw me dressed for a date in a sports jacket and a shirt with a tie. Naturally, this brought on many questions about who the girl was and how I happened to meet her. Jenny rescued me by saying that this was a blind date that she had arranged with the girl at the beauty salon. That was close enough to the truth that both of us could work with it, and Mom and Dad were not suspicious.As with Alice, Janice picked me up with her car and drove away from my house. This was essentially a middle-of-the-week date, so we did not encounter any of Janice’s friends either at the restaurant or at the movie. This was fine with both of us, and I was delighted when Janice selected a comedy instead of a chick-flick for our movie. There were a couple of chick-flicks showing in town, but I thought both of them were kind of depressing and not suitable for our kind of date. Fortunately, Janice agreed with me.I was also happy because the movie ran only 84 minutes, and that gave me a little extra time to work on Janice. She drove us to her favorite parking spot, and we moved to the back seat where she had thoughtfully placed some towels before she left home. Since we hardly knew each other, even by sight, we spent a little time talking to get to know each other a little better before we moved on to sex. It really didn’t make much difference to me, but I thought Janice appreciated the interlude.

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