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Jenny and I-4

Janice was a bit tentative at first, but I let her set the pace since she was paying for it. I wish I could say that it was my great technique that moved us along fairly rapidly, but, in all honesty, I must admit that Janice proved to be very horny when she warmed up a bit.

Janice took her own blouse off simply because I was trying not to push her too hard, but it took less than 10 minutes for us both to be naked from the waist up and locked in a lovers’ embrace. Neither one of us needed instruction in French kissing, so we took that route very early on in the date. We kissed for a few minutes, and then I slid my hand up to grasp her right breast. It was as if a starter’s gun had been fired and we were off to the races. Jenny had helped me to learn how to remove my date’s panties while still sucking on her nipple. Thus, a few minutes were saved, and Janice was already dripping lubricant from her pussy.

Janice was wearing stockings with a garter belt instead of the usual pantyhose. I presumed that she was doing this because she felt sexier dressed that way. I can go along with pantyhose in a working environment, but I much prefer the separate stockings and panties for a heavy date. Again, it was Jenny who clued me in on the relative advantages of the different kinds of female attire.

I pulled her panties down to her knees and paused long enough to remove her shoes. Jenny had shown me what an aggravating nuisance high heels could be when I was trying to remove my date’s panties. I got past this little roadblock very easily and was ready to progress to removing her skirt. I had no intention of removing her stockings or garter belt unless Janice specifically requested it. It had never happened to me before in real life, but those porn movies that I had seen on the web sure were sexier when the woman was wearing stockings and the garter belt. I wanted to go whole hog on my own enjoyment if I could get away with it, so I waited for Janice to tell me her preference.

Her pussy was as clean as a whistle (I saw that phrase in a book once), and it certainly looked perfect to me. She had the classic Camel toe with no sign of her inner lips or her clit. All I could see was her two very puffy outer lips with a pristine slit separating them. I had heard from some of my friends who considered themselves to be very sophisticated on the subject of pussies that a woman who did not have her inner lips at least showing a tiny bit just had to be too young to appreciate sex. Well, I had always thought that those guys were full of shit, and now was my chance to verify my assessment of their sophistication. Anyway, I was a fan of the classic Camel toe, and I was delighted to see it attached to Janice.

Janice was wearing a kind of wraparound skirt that was very easy to remove. I had that off her in only moments after removing her panties. You may note my careful consideration of my client because I dropped all of the clothes removed from Janice onto the front seat where they would not be soiled by whatever might be on the floor. I doubt that Janice made any note of what I had done with her clothes, but I was sure that she would appreciate my consideration later on when she got dressed to return home.

Janice wanted to remove my trousers, but she could not conveniently reach my shoes. I had planned ahead on that and was wearing some black loafers that simply slipped off my feet. I was not wearing socks, and I was not wearing underpants, so all I had left to remove was my trousers. Janice took delight in unfastening my belt and opening my fly. She squealed when my already stiffening cock jumped through the open fly and pointed at her face. Undoubtedly, she had been expecting some sort of underwear, so she was caught by surprise when the Jack-in-the-Box jumped out at her. We both laughed at her reaction, but quickly returned to our main reason for being parked where we were.

She caught me by surprise by grabbing my cock with her hand and pulling me to her mouth. I must say that I was truly impressed by the quality of the blow job that she gave me. I called for her to stop before I came in her mouth, but she pointedly ignored me and continued with the blow job. I don’t know who or how many guys she had blown, but she did seem surprised at the quantity of jizz that I deposited in her mouth. Just as any hooker would have been expected to do, Janice opened her mouth and showed me the jizz collected on her tongue just before she swallowed it. This convinced me that my client was a woman of experience, and I was anxious to see what else she had to show me.

She wiped my cock with one of the towels so that I would not drip on the upholstery, and I slid another towel under her ass to collect the drainage during and after our fuck. At this stage in my life, it took me about 15 minutes to recharge my jizz supply, so this was the perfect opportunity for me to eat her pussy. It was a thing of such beauty that I was determined to put my mouth on her pussy unless she flatly objected, and I did not expect that to happen.

In an effort to return to our previous activities, I slid down onto the floor to kneel there and put her ankles across the top of the back of the front seats. That boosted her pussy plenty high enough for me to reach the whole thing so it only took a few moments for us to achieve the proper positions. Janice was not surprised because I had told her what I intended to do, and she seemed thrilled by the prospect. She claimed that her pussy had been eaten several times, but by boys who really did not know what they were doing. I assured her that I intended to make this a special occasion for her enjoyment.

I started out by licking her outer pussy lips, going from the right lip to the left lip and back all the way from the bottom of her slit to above her clit. I made about 10 passes on each outer lip before I tried anything else. By the time I was only halfway done, Janice was drowning in the spirit of the thing. She was panting so hard that I half expected her to hyperventilate, but that didn’t happen. She was moaning in sync with my licking by the time I finished my total of 20 strokes and switched my target.

This time, I traveled up her pussy slit putting gentle pressure on it with my tongue. The second pass was enough to f***e it open so that I could reach her inner pussy lips. When I make contact with them, I thought she was going to explode! She had a major orgasm right then and never seem to come down completely from it the whole time that I licked her. She was gushing liquid from her vagina and bouncing around so much that I could hardly maintain contact with her.

When she did come down enough so that I knew I would not injure her, I grasped her clit with my lips and sucked as hard as I could. This pulled her clit from the sheath far enough for me to nip it with my teeth. Yes, I have practiced this with Jenny and knew that I was not going to hurt my client. That nip was enough to make Janice scream loud enough seemingly to be heard for miles. Several other cars were parked in the general vicinity, and Janice’s scream was loud enough to cause some horn honking in response. I couldn’t help laughing, but Janice never noticed.

I sucked on Janice’s clit for a little longer and did gently bite it a couple of more times, but I started backing down my stimulation of her pussy, so that she would have something left for the fucking that was coming up. I definitely did not want to burn her out too soon. I fully intended to give Janice her money’s worth!

It was not an easy thing to do, but I did manage to squeeze in beside her to cuddle with her while she came down from her series of orgasms. That woman held onto me as if she feared that one or both of us was going to float away. There was no doubt that I had gotten her full attention.

I didn’t want this date to run too long and chance making trouble for Janice when she got home. Therefore, as soon as I thought she was ready, I suggested that we proceed with the climax of the evening. Supposedly, Jenny had already made sure that Janice was fully protected from pregnancy and had no STDs (Sexually Transmitted Diseases). Nevertheless, I did ask her the necessary questions because I wanted her to realize that I was concerned about potential consequences. She assured me that she was taking the Pill, and that she had recently been tested and cleared of STDs.

Okay, that was good enough for me because I knew that Jenny would not fumble the ball with something as serious as this. I did tell Janice that I would wear a condom if she preferred it, but I did not believe that the added level of protection was necessary. Janice agreed and even emphasized that she was anxious to feel my bare cock rubbing inside her pussy. As far as I was concerned, the question was settled and needed no further discussion.

Because the seat was rather narrow and Janice had wide hips, we decided that she should rest her left heel on the package shelf behind the back seat and her right heel on the back of the front seat. That got her spread open adequately and gave me plenty of room to operate. I made a mental note to make sure that what ever car I bought had a wide backseat. It was my intention to stay out of motels until I graduated from high school.

Naturally, by this time, Janice was thoroughly lubricated, and I felt that I should be able to slip right in with no further foreplay. Janice wanted to “help,” so I had her aline my cock with her pussy hole and guide me in as I penetrated her. She giggled and said that no one had ever penetrated her with so little fuss, even though I was somewhat larger than anyone she had ever accommodated before. Well, I grunted some innocuous remark and got down to business.

Janice turned me loose, and, as expected, I slid all the way in with my initial push. Fortunately, Janice was deep enough for me to bump her clit with my pubic bone without banging against her cervix. Ah, that made life a whole lot simpler! I held still when I got all the way inserted to make sure that Janice had adapted to my size. That turned out not to be a problem, and she urged me to begin stroking.

I certainly don’t need to be asked more than once to fulfill that request. My first three strokes were rather gentle, but I could tell from the look on Janice’s face that she wanted more than a gentle fuck. I had no trouble speeding up my stroke rate, nor the f***e with which I bottomed out. I was really surprised to see that Janice began to rise to an orgasm by my second quick stroke. I could not help wondering what I was dealing with, because this was totally outside my experience. Nevertheless, Janice was enjoying it, so I saw no reason for us not to keep on with what I was doing.

Janice reached her first fucking orgasm in something less than 30 strokes, and she came hard! The only thing I could think of to explain her quick reaction was the effort I had put into my exercise in cunnilingus. Anyway, I was so in awe of the effect I was having on Janice that she came three times before I did. Even at that, she came again when I started squirting in jizz. I swear, that woman appeared to me to be a walking sex machine!

We had to wait almost 40 minutes before Janice had settled down enough to get dressed and to be able to drive. During that whole time, she kept on complimenting me about how good a fuck I had given her. It was almost embarrassing to hear all of that praise, but I somehow kept it from going to my head (I think!). As she was driving me home, she kept pushing to know how long she had to wait before she could hire my services again. Of course, I had no answer to that, since it all depended on Jenny’s scheduling.

All I could tell her was that she should talk to Jenny about arranging another date. Janice was disappointed that I would not commit to a specific date, but I guess she learned how boys feel when girls give them that kind of run around. I really liked Janice, and I hoped that she would not get pissed off at me because I would like to fuck her again. Of course, that $250 payoff was nothing be shrugged off for a boy of my age, and economic status.

I tried to look presentable as I walked in the front door because I knew my parents were going to be waiting to hear how things had come out. I spent about 15 minutes giving them a much watered-down version of the date before I could escape to my room. Naturally, as soon as I got there, Jenny waltzed in and demanded a full rundown on the date. I had no trouble with that, since this was a business operation, and not a social one.

Jenny said, “Janice Upton must have been hot as a firecracker! Apparently, the word of mouth advertising going on about you has lost nothing in the retelling. I’ll bet that I hear from Janice tomorrow about scheduling a second date. How do you feel about that?”

“Hell, Janice was a great fuck! I wish I could get somebody that good every time! Go ahead and set her up for any time that is available. If she talks about her experience to other Senior girls, you should be beating away customers before long.”

“Okay, I’ll try to keep space open for her.” Jenny laughed at that point. “Meanwhile, here is your $225 for tonight’s performance. It looks like I have two more dates set up for next week, but I have not seen any money, yet. I’ll keep you posted.

“I guess you are too tired tonight to give me a ride. Can we schedule something for tomorrow afternoon before the folks get home from work?”

“Sure, Jenny, you know that you are my favorite fuck, and I would turn down anybody else for you. However, money does shout pretty loud. I hope I don’t have to start charging you for fucking just so that I can get some time with you!”

Jenny gave me a funny look when I said that, but she relaxed when she saw that I was laughing. Dammit, it was true that I would prefer to fuck Jenny over any other woman I had met so far.

Things were going so well with our little prostitution racket that I was scared that something would happen to blow it out of the water. I suppose, the worst thing that could happen would be for my parents to find out what I was doing in my spare time. They were not prudes, but I was pretty sure that my mother would not approve of me being a gigolo. On the other hand, Dad might laugh and slap me on the back. Everything considered, I would be just as happy never to find out what they felt about my new profession.

The next morning, I was out walking around the neighborhood just enjoying being alive. I had no jobs scheduled for that morning, so I was dressed in my usual casual summer attire of canvas shoes, short shorts, and a T-shirt. I had walked about three blocks when I heard myself being called.

“Billy Weston, do you have a minute?”

“Sure, Mrs. Arthur.” I smiled my most fetching smile and said, “I always have time for you! What can I do for you?”

“Well, Billy, my first request is that you come closer, so I don’t have to shout at you.”

I walked over to see what Mrs. Helen Arthur had to say. I had just recently mowed her lawn, so I was pretty sure that was not what she wanted me for. More than likely, she wanted some furniture moved or something like that. I tried to make a point of staying on the good side of my regular customers, so I was prepared to do pretty much whatever Mrs. Arthur requested.

As soon as I got up on the porch, Mrs. Arthur grabbed me rather f***efully by my upper arm and practically dragged me inside her house. She made a point of closing the door before saying anything to me, but then she dropped a real blockbuster on my head. “I was talking to Ruth Jackson yesterday afternoon, and she told me of the special services you offer to your regular lawn care customers. Frankly, I wondered if that extended to a woman of my age?”
“Mrs. Arthur, I would make you a special case if that ever became necessary. However, I wonder exactly how much accurate information you got from Mrs. Jackson. Did she tell you about my new profession?”

“No, I don’t recall Ruth making any sort of comment along that line. What do you mean?”

“Well, I guess you know that it is the ambition of every k** my age to own a set of wheels. I think it is obvious to anybody who gives serious consideration to the question that there is no way that I earn enough money mowing lawns ever to be able to afford a car, even a used one. Therefore, I have decided to branch out and to offer my services as a gigolo in order to raise enough money to be able to buy a decent car.

“I have already earned around $1000, and I hope to have enough money to afford a car before the bad weather of winter sets in. My current feeling is that I will charge a flat $250 for half a day of my undivided attention. I have had a very good teacher, and I am sure that I can give any woman the treat of her life. In other words, as long as it is not painful to either side or harmful to either side, I offer my services for half a day for $250, and I will attempt to do anything that my client requests within the previously stated parameters.

“Notice that the $250 rate is for a one-shot appearance. If the client wants more than a single visit with me, then I will reduce the rate to $200. That’s the way things stand at the moment; would you like for me to add you to my client list? If you should decide that you want to go the $250 route, but decide later that you would like to become one of my regulars, then I would be willing to refund $50.

“How does that sound to you, Mrs. Arthur? Would you like to try me out to see if I am really worth that much money? I assure you that I am, but I can make adjustments to fit my clients desires.”

“Frankly, Billy, I had no idea that you were prostituting yourself. On the other hand, with inflation being what it is, I can understand why you are doing it. Never before in my life have I ever hired a gigolo, so I really don’t know what to expect from you if I do hire you.”

“Well, Mrs. Arthur, I have been told that I should never give free samples, so the question really is whether or not you trust the word of Mrs. Jackson as to the quality of my services. I promise you that you will not be disappointed, but you only have my word and the word of a very satisfied customer. What else can I say?

“This morning is half gone and I have a commitment for this afternoon, so tomorrow would be the earliest that I could show up to service your needs. Perhaps you would like to think about the situation for a while before committing yourself. If so, that is fine with me. You have my telephone number, so you can call me for an appointment whenever you make up your mind. All I ask is that you do not say anything about this new career to my parents.”

“Okay, Billy. I’ll give your proposition some thought and let you know my decision. I hope you realize that $200 or $250 is a big wad of money for a widow to shell out for a few hours of sex. I am interested based on what Ruth had to say, but I will have to think about it. I will telephone you if I decide to take you up on your offer.”

Jenny and I had our usual very pleasurable tumble that afternoon when she got home from work. For some reason, Jenny wanted the reverse cowgirl position, and I never argued with Jenny when it came to sex. That is not one of my favorite positions, but I agreed wholeheartedly with Jenny that I needed to become an expert with it. With one thing and another, we only had time enough for two rounds of reverse cowgirl before we had to shower to get ready for our parents coming home.

After we got dressed, we stayed in my bedroom and discussed business. Jenny now had three commitments for the evenings next week, so things were really looking good for our business. That’s when I put my foot in it! I told Jenny about my conversation with Helen Arthur, and Jenny hit the ceiling, “Billy, you have got to stop making commitments like that! You could get into serious trouble if one of those women complained to the cops. If she had not filled out one of those forms I wrote up, she could charge you with soliciting her for prostitution.

“Things are entirely different with you and the high school girls versus you and these older women. Our tie up with Janice Upton will probably be all the protection we need from that side, but these older women don’t have a reputation they would want to protect, if one of them really got pissed off at you. If Helen Arthur calls for an appointment for your services, be damned sure you don’t commit to anything until after she has talked to me. Furthermore, the next time Ruth Jackson propositions you, make sure she talks to me before you agree to anything. We have got to protect our asses! I am just about old enough to be tried as an adult, so that I could spend some real time in jail.

“At least with you, you are still a juvenile as far as the court system is concerned, and you would probably not spend any time in jail, but we would all have to move out of this town if the word got out that you were a gigolo. I commend your entrepreneurial spirit, but, dammit, you have got to learn to protect all of our asses. Just one slip could get us into a world of trouble!”

Thank God our parents selected that moment to show up and to call for us. That f***ed the end of the conversation, and I was glad for the relief. We went downstairs and Jenny managed to cool off before we ran into our folks, so the secret was still safe for a while.

Three dates next week would amount to $675 toward a set of wheels for me, and how else could I possibly hope to earn so much money doing something that I enjoyed so much? At the rate I was going, it was quite possible that I could have enough money to afford a good car long before I could legally drive it. Man, it was going to be hard to sit on the money for several months. Maybe I could arrange for Jenny to buy the vehicle and be the official owner while I drove it with a learner’s permit. That could get pretty complicated, but maybe we could work something out.

Mrs. Helen Arthur did not take long to come around, if you will pardon the weak pun. A couple of days after I talked to her, Helen telephoned Jenny at the beauty parlor to find out how to make an appointment with me. Jenny quoted her a price of $250, but with the rebate if she became a steady customer, and Helen stopped by to sign the hastily revised form that Jenny had come up with. Therefore, at 9:00 AM on the following Thursday morning, I showed up at Helen’s house ready to take on my first senior customer arranged through Jenny.

Of course, I had bathed and was dressed in my usual “non-working” summer attire. I rang the doorbell precisely at 9:00 AM and Helen opened the door so quickly that I thought that she must have been standing by the door waiting for me. She was wearing a sundress and nondescript house shoes, but her hair was fixed nicely and she was wearing some makeup, so she was pleasant to look at. She had already paid Jenny the $250 fee, so there was nothing left to slow me down.

I was a little taller than Helen, and I had no trouble gathering her into my arms for a kiss. She was a little surprised at my action, but was in no way reluctant to move into the spirit of the game. Helen returned my kiss, and we shifted into a French kiss before breaking contact. I could tell that Helen was a bit nervous, and I was not surprised, because this was her first experience with a gigolo.

I took her hand and led her to the sofa where we both sat down very close together. My recent visits to the back seat of cars with a girl had given me plenty of experience to follow through with Helen. I simply treated her as another one of my high school “dates.” I put my arm over her shoulders and drew her close for another kiss. This seemed to fit with what she expected, and she melted into my arms as if we were long-lost lovers.

I held her and kissed her for a few minutes without making any other moves. However, before long, Helen had taken my hand and placed it against her breast. That was when I discovered that she was not wearing a bra. It was easy to rub the palm of my hand over her projecting nipple as I gently massaged her tit with my fingers and thumb. This went on for a few minutes until Helen decided to stand up.

She grasped my hand and led me to her bedroom. She had already prepared her bed with a towel lying across it where she had planned to put her ass. We approached the side of the bed, and I stopped us by pulling Helen into another deep French kiss. I drew the kiss out as long as I thought she would like it, and then I backed off just a little to provide enough room for me to remove her sundress. To my surprise, I noted that she was not wearing panties and that she had shaved the hair from around her pussy. Aha, that was all of the hint I needed to know how to proceed.

I gently pushed Helen onto the bed and removed her shoes. I left her lying on her back as I quickly shucked my clothes. As usual with such an engagement, I had worn no underwear, so my semi erect cock jumped up to greet Helen’s stare. This was her first chance to see my equipment, and her eyes bulged a little bit in happy anticipation. I would have bet that Helen was finally beginning to believe all that she had heard from Ruth.

I stood there for a few moments, so that Helen could gaze at my cock as it rose to full erection. Just the sight of my cock was enough to cause some change in her breathing. She had actually begun to pant a little bit just from seeing and contemplating what was headed her way. I climbed onto the bed between her legs and lay across her body with my cock pressing against her pussy and my chest pressing against her tits. I stayed like that for another round of French kissing. So far, Helen was cooperating with an enthusiastic attitude, and I figured that I was giving her what she wanted.

I slid my hips up and down so that my cock rode along her pussy slit and did put some pressure on her clit; however, I was careful to make sure that there was no penetration by my cock. I wanted to tease Helen a little bit with the thoughts of what I might do next. After a few sliding strokes on her pussy, I moved my whole body down toward her feet without ever breaking contact. I stopped when I got far enough so that I could reach her pussy with my tongue. After all, Helen had paid for the full experience, and I intended to give it to her. I fully intended to leave with a well satisfied customer who would want my services again.

I began the session of cunnilingus by holding her hips in place with my hands and rubbing my extended tongue along first her right pussy lip and then her left. I went all the way to the top of her pussy from the bottom, but I made a point of not touching her clit with my tongue. There was no way I could avoid licking her inner lips at the same time that I licked her outer ones, since her inner lips did project that far out of her pussy slit. I gave her a dozen strokes with my tongue on each side of her pussy before I switched to licking directly into her slit.

By this time, her clit was standing out and there was no way for me to avoid it had I wanted to. However, I made a point of licking her clit when my tongue got that high in her slit. Helen was already breathing hard and her panting was becoming noticeable; however, when I touched her clit with my tongue, she gasped so hard that, for a moment, I thought that I might have hurt her. Helen returned to panting, though, so I figured that it was just the shock of me touching her clit that had caused the change in her breathing pattern.

At this point, I used my thumbs to draw open her pussy lips to expose as much of her clit as possible. Helen’s clit was of average size, so I had to dig a little with my lips to reach it well enough to surround it so that I could suck on it. I put a significant vacuum against her clit and managed to pull it out of the hood a surprising distance. This caused another change in Helen’s breathing pattern, and I could tell that she was rapidly approaching an orgasm.

I drew her clit as far as I could from the hood with my applied vacuum and then began to strum on it with my tongue. This brought the reaction that I expected, and I had to hold onto her hips to keep her from jerking out of contact with my mouth. Now, she was rapidly rising to orgasm, but she seemed to hang without ever quite reaching the peak, so I knew that I was going to have to give her a boost. That boost consisted of a gentle bite with my teeth onto the end of her clit. That was all that she needed to push her over the precipice into a very strong orgasm. I had no idea that Helen was a squirter, but my chin was bathed in her lubricating fluid as it shot out during her orgasm.

Once started, there was no moderating Helen’s orgasm. Frankly, this was the strongest orgasm I had ever encountered with any of my customers. Helen was bouncing her hips in orgasmic bliss so hard and fast that I had to jerk my face away from her pussy to keep either one of us from being hurt. She even managed to jerk her hips loose from my hands, so I just backed away and let her enjoy her come. She continued to shake for some time, and I secretly figured that she had gotten her money’s worth just from that orgasm, but I intended to give her the rest of the treatment that she had paid for.

It was obvious Helen was going to need some time to rest, so I lay down beside her and let her relax. It was not long before she pulled me into a lover’s embrace and held me for about 10 minutes. Finally, she let me go, and said, “Ruth was right, you are worth every penny! I have never had an orgasm as strong as that one, and you have not even penetrated me yet. Come on, Stud, I can hardly wait for the next act!”

I grinned at her and returned to a position between her legs. Helen’s pussy rode so high that I was going to have no trouble reaching it with my cock, so it was not necessary to put her legs on my shoulders. However, Helen must have paid more attention to Ruth than I had expected, because she put her ankles on my shoulders as soon as I was close enough. Of course, this boosted her pussy so high that I had to be careful with my alignment. That was no big deal, except that I had to be sure that I did not pinch any part of either Helen or me.

I had little to do with getting properly aligned because of Helen’s impatience: she pulled on my cock until it was lined up with her hole and spread her lips with the fingers of her other hand. Almost before I knew it, my cock head was resting against her vagina opening, and all I had to do was to push to make my entry. Helen was so thoroughly lubricated that I was able to slip all the way in on one gentle stroke. I bottomed out without striking her cervix and earned the delighted squeal I expected from the impact of my pubic bone against her clit.

A couple of slow strokes insured that I was properly aligned so that I rubbed against her G-spot with every stroke. I considered that to be my trademark, and I intended that to happen with every one of my customers. This was pretty much of a standard fuck, so there is not much to say about it, except that I was able to hold off long enough for Helen to come three times. Her third come coincided with my orgasm, and she reveled in the feel of my jizz jetting into her tunnel.

Helen was exhausted by so many orgasms, so she was ready to call it a day. I had also thoroughly enjoyed the experience, and I was ready for some rest away from sex. It was amazing to me that these older women could be as energetic and receptive to sex as the high school girls: that shows you how limited my experience was.

I rested for about half an hour and then showered before dressing. As I was leaving, Helen said to me, “My Lord, but you are better as a stud that any man I have ever heard of! Yes, Ruth certainly was right, and I will start saving my pennies so that I can become a regular customer!”

I thanked Helen for the compliment and headed home to rest before Jenny showed up from work. Without a doubt, I needed the rest before I tried to service my s****r!

Updated: October 21, 2016 — 1:22 pm

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