How I Became A GigoloChapter 3 free porn video

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I 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 kid 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 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.

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Showertime

The sun was just peaking through the over cast sky, pushing its way in through the curtains and across my sleep crusted eyes. I blinked and stretched up, arching my back as the soft cotton sheet slipped down. It felt luxurious and I reveled in the rare opportunity to sleep in with no obligation, school, or extracurricular activity to take my time. Rolling over, my legs rubbed against each other smoothly as they tangled in those worn sheets. I yawned and listened carefully. No sounds permeated...

2 years ago
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Tradeshow1

‘So how may I help you today?’ I asked. ‘I’m not sure you can’ she replied. Her voice was very quiet, self assured. ‘Try me’ I said giving her my best smile. She paused and looked around before looking up at me as if contemplating her next words. ‘I’m looking for some advice for a project’. She stated very matter of fact. ‘Ok, why not tell me what it is that you are looking for and I will see if I can help?’ ‘Maybe’ she replied and turned away and started to read some display material. Her...

4 years ago
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Howards Sister

By Gail Holmes Howard glumly sat at the kitchen table taking note of his Mothers advice she was always good at giving it out, He could but pay attention; he knew she wouldn’t resign until she’d had her say. “Well, don’t just sit there! Am I right or wrong” She turned Howard’s father with a fierce look that could have killed him. If anyone was under the thumb, it was poor old Ray he had more than suffered the wrath of...

4 years ago
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Howd that happen 6

I pulled my horse up up aside of the wagon, leaned over and said “Well, ladies, we’re going to make it into Sante Fe in a couple of hours, but you both look a little trail worn. We should pull over by that stream there, rest the horses so they look perky, and maybe spruce up a little. I could use a wash and shave myself.” “ Horse, that’s one of the better suggestions you’ve made lately. I feel like I’ve been rode hard and put up wet,” Sandra retorted. I kind’a snickered at the rode hard bit,...

3 years ago
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Howd that happen 11

When I left Sara’s place it was still fairly early morning and as I walked down the street I received a few small smile, and nods, but none of the wary looks I had received yesterday. Seems that word had gotten around that I wasn’t the enemy, even though I couldn’t figure out how it had spread so fast. Smoke signals, maybe? I guess it’s just that no matter how fierce a people can be in war, they’re just people, nevertheless. Not that these people didn’t have a reason to be distrustful of the...

3 years ago
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Howd that happen 4

These stories are meant to be read serially. I woke with every intention of following my last thought last night to get things organized and re-start our journey. And I would have too, but I looked next to me on the bed at the gorgeous naked lady and thought “Well, it is still real early, and I don’t want to rush into anything. And it looks a little rainy outside. Besides, I don’t hear Tom and Sandra rustling around yet. They probably need more rest, so I think I’ll just lay down aside of...

4 years ago
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howd this happen 8

When we woke in the morning Jack and I almost were caught sneakin’ out the back door but I think we got away clean. We got our horses, I told Jack I’d see him later, and I left for home. When I entered the gate Pablo urgently motioned for me to pull into the stable without waiting to get off the horse. After I entered and did get down he said, “Senor Sam, I think someone is spying on you. I don’t know if they want to hurt you, but I thought, to be safe, you should not pause in the yard.”

3 years ago
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Howd that happen

“What the hell is the screaming about” I thought as I pulled my horse up. Another sharp yelp split the air, but this one sounded like a different voice but was definitely female as was the first. I was almighty curious as you don’t ordinarily hear such some days away from “civilization”. Dismounting and tying my horses, I pulled my rifle from the boot and snuck through thru the trees ’til I could see into a clearing. There was a small wagon off to the side with two draft horses ground staked...

3 years ago
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Howd that happen 9

When I awoke I discovered that Naomi must have silently slipped away sometime during the night. Damn! I guess I shouldn’t be greedy, she is living here too, so that’s a good thing, and I had plenty to do today anyway, what with moving the girls here from the hotel. While I was dressing there was a knock on the door and I rushed over to open it. Maybe Naomi just left for a few minutes. Damn again! It’s not her. Instead there stood a tall, middle aged, gray haired lady with a long all black...

4 years ago
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Howd that happen 10

I had set my internal clock and woke well before dawn. I wanted to check on Pablo to see if he was alright and how much damage had been done to the house. After checking on the guards around Sadie’s house I hurried to mine. I almost silently approached, only softly whispering, “Pablo….Pablo,” when he answered from the stable. “Here, senor. I have been sleeping and watching from here. They can’t get a clear shot at me here. All the windows have been shot out except here in the back where the...

3 years ago
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Howd that happen 2

I woke up startled. I couldn’t figure out why I was naked as a baby. Then I looked around. When what to my wondering eyes should appear. Was this Christmas? What the hell did I do to deserve two gorgeous, naked, sleeping, girls lying aside of me. Then my memory cells started firing. WOW, did that really happen? And if it did, could I repeat it? Taking stock of myself I realized that, yes, maybe I could, but not right now. I was goin’ to have to recuperate a while first. I cleared my throat...

3 years ago
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Howd that happen conclusion

When I awoke the next morning and got off the bed I was greeted by a sight I’ll never forget. There before me were three puffy pussies, six bountiful breasts, and seemingly uncountable shapely arms and legs, all entwined in such a combination that it was hard to be certain which body part belonged to which body. If I had only a modicum of artistic talent and the right equipment I would have put such amateurs as Rubens to shame. Unfortunately, although it was an extra large bed, with one small,...

3 years ago
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Howd that happen3

Comments/criticisms are welcomed by me. These stories are meant to be read serially. The next morning I was barely able to get off the ground. It seems something else did come up and I was able to cope with it. Barely. Those ladies almost did me in. This morning I felt like I might not make it so Sante Fe if this kept up. After thinking about that for a while I smiled to myself and figured, what the hell, if it happens I don’t make it I can’t think of a better way to go. But we really had to...

3 years ago
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Howd that happen 7

I woke up feeling pretty chipper, The sun had just come in the window and it looked like a real nice day. My houseboy and all around caretaker, Pablo, must have heard me stirring around and getting up and dressing, ’cause he showed up with another damn cup of hot chocolate. “ Damn it, Pablo, I’ve told you I like coffee, not chocolate, in the morning.” “ No, Senor Sam, chocolate is best in the morning.” This is the same argument I’d had with him every damn morning since I hired him. I know,...

2 years ago
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Howd that happen 5

How’d that happen 5 These stories are meant to be read serially. The first ones can be found on my profile We got up the next morning pretty late as the sun was already above the hills on the horizon. We were determined to make good time so for the next days we really hustled with only a few invigorating interludes. What with hard driving from almost dawn to dark, we were pretty exhausted at the end of the day. I was becoming especially burned out as the girls could alternate when it came to...

2 years ago
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Sunshower

The rain: that's how it all began. Hannelore was standing in the breakroom, staring out the window with an increasingly grim expression. The disproportionate enormity of the window made her look smaller than she actually was, shrinking into nothingness in the shimmering void of the rain. She'd already changed, so she was wearing her street clothes -- nothing special, just a pullover hoodie and jeans. The front pocket of her sweatshirt tightened in her balled fists. "Shit," she muttered,...

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