2 comments/ 113762 views/ 6 favorites Teen Age Gigolo By: thongcladtommi There is no use hiding the facts. At 18, I was a male gigolo. I earned my money by satisfying the carnal needs of older women in our town. Our town was not a big town by any means; but you would have been surprised at the number of older, unsatisfied women in town. Once the husband hit 50 or so; or became succesful in business; or just got bored with the wife, her frustrations would begin. Some of these women were raving beauties. Some had seen better days. Deep down, they all needed to be reassured they were still attractive. That's where I came in. Truth was, if some of the husbands had just treated their wives like whores, I would have been out of circulation. Six days a week I was busy. On school days, I might have 2 "dates". On non-school days, I would average 4 to 5 dates per day. There was just that much unhappiness in the town. What pleasures for me however. I remember one particularly well. Her husband was a prominent lawyer. When he wasn't working, he was at the country club or out of town on golf outings. If he was away overnight, it was normal for her to be my last stop of the day; and I would stay overnight. I arrived one evening around 7:00. She answered the door; by her attire, I knew he was away for the evening. She'd kinked up her hair the way I liked it. Extremely heavy makeup and lipstick were added. She was wearing heels, bikini panties, and a gold necklace. She was in her mid-50s. I'm not normally turned on by thin women; this one was different. She was only 5 foot tall and weighed in at about 90 pounds. She worked out and had a trim figure. She was meticulous in appearance when out in public. Her pussy was shaved; she knew I liked that. Her hair was grey; but she did not appear old. She greeted me at the door with a heavy kiss; it was almost like she wanted one of the neighbors to tell her husband. She was almost bouncing like a school girl as we went into the living room. The patio door drapes were open; a nosy neighbor would have seen us. I often wondered if she was that unhappy. She knew I'd had several other dates that day; yet that was not a problem for her. She even knew some of the other women I serviced. Before we started that night she told me she had a favor to ask of me. Her college roommate was coming to town and she wanted me to do a 3-some with them. I agreed and could see the sense of relief she had. We were standing by the slider as we began kissing. I had to bend down some due to her height; and she always rose up on her toes. Her hands were around my neck as we french kissed. My hands were on her ass; I was squeezing and rubbing through thin silk panties which barely covered half her ass. She could feel my hard on through my shorts; and seemed to enjoy rubbing against it. She pulled her lips away long enough to express her desire to be treated like a whore. I promised she would feel used and abused when I finished. I lifted her from the ground and turned to retreat from the doors. I did not want to be the cause of family problems. Her children were away at college; heck, I had dated the daughter while she was in high school. Mona shook her head no; she apparently enjoyed being on display with her boy toy. I resumed french kissing her; her lips were wrapped around my tongue as though she was giving a blow job. That was fine by me. She did give great head. She wrapped her legs arond my waist. I lowered my hands slightly on her ass so I could run my thumbs across her pussy. Her panties were soppy wet; this would be a good fuck. Her motor was running wide open. She was so light. I lifted her higher and placed her legs across my shoulders. My face was in her crotch; and I began kissing her mound through those panties. My tongue began driving into her slit; and I could feel her clit quivering as my tongue lapped at it and my teeth nipped on her pussy lips. I kept this up for 10 minutes or so as she hit one orgasm after another. She was cumming so much the excess juices were flowing out the legs of her panties and onto my chin and shirt. I stepped back a couple of feet and began to lower her to the ground. She knew what I wanted. As I began to peel off my shirt, she unsnapped the waist button on my shorts. My shorts fell to the floor as my cock sprang forth. She took my cock in her hand and began lightly tonguing it. Her mouth opened wider; her lips formed around the head as she ministered that tongue all over the pee slit. Apparently my cock head had a larger pee slit than most men as she took her time using her tongue to force it open. I could actually feel her mouth cum enter the head of my cock. She was on her knees; and I lowered myself to the floor. Her mouth never left my cock. I lay back on the floor as she continued administering a superior blow job. Her head was bobbing up and down as her lips maintained a tight grip on my cock shaft. She lifted her head and smiled that devilish grin. I motioned her to turn around and back her pussy to my face. As she did so, I tugged her panties off the pussy and resumed eating that shaved pussy. It was oozing creme which seemed to thicken with each slap of my tongue on her clit. Every woman I had ever eaten told me how well I did that; and how they wished their husbands could take lessons. That white creme was so sweet and tasty; I could not get enough. I finally slapped her ass and told her to climb on for a ride. She knew what I meant. She moved forward and straddled my cock. Her back was to me and she lowered that sloppy pussy onto the head. She began rising and lowering herself onto my cock. She was riding up and down like a bull rider in the rodeo. I began to picture her with a cowboy hat and chaps; perhaps another time. She rode up and down for about 10 to 15 minutes. She was hitting orgasm after orgasm. She came so hard and frequently her juices were flowing onto my balls and pubic area. That was one of the reasons I always shaved. I did not want to leave with a smelly residue in my pubic hair. No hair meant no pussy smell. I slapped her on the ass and told her to climb off. She had that disapointed, spoiled little rich girl look on her face as she climbed off. I told her to get on her knees and elbows as I wanted to fuck doggie style. She squealed with glee as she positioned herself. I got behind her and positioned my cock at her pussy hole. It was gaping open and was still soppy wet. I took hold of her ass cheeks as I began to push my cock in. She was so open, I went into the base of my cock. I was holding tight on her ass as I began pumping my cock in and out. Her pussy took it all. I was fucking her hard; driving my cock deep into her with every thrust. I looked out the doors and saw the nosy neighbor watching. What the hell, I thought. If Mona doesn't mind, why should I. I lifted one of my hands and blew a kiss at her. She still kept looking at us. I wondered if this would be a new client. As I put my hand down, I spit on my thumb and began running it around her asshole. She seemed to like that. Right then, I decided to drop my first nut load into her asshole. I continued fucking her hard. I had conditioned myself to control the release of my loads; and this was my fourth fuck of the day. My balls were slapping her pussy lips and clit as she continued to squeal and orgasm. That woman had a never ending ability to cum. My thumb had loosened her asshole enough that on my next pull back, I removed my cock. As she moaned in disappointment, I positioned my cock head at her ass and began to thrust it in. Her head shot back as my cock head went deep into that asshole. I slapped her ass cheeks to get her mind on something other than the cock which was ripping her ass apart. I began driving deep and hard. I slapped the ass cheeks; and told her to wiggle and fuck back into me. She did. I fucked another 10 minutes or so when I felt my load begin to build. That tight ass brought it on quicker than was the norm. She would have to work hard to get the next one. I tightened my grip on her ass as I began to unload my cum. Spurt after spurt spewed forth into her anal cavity. She was in her glory. I took my time extracting my cock from her asshole. She fell forward to lie on the carpet. She was used but not quite abused. I rose up and walked around. I dropped onto my knees and held my cock in my hand. It was coated with thick white creme and some brown globs; I knew what they were. I lifted her head and told her to open wide. She knew her job was not finished until she had done clean up on my cock. She looked for a few seconds; she saw the brown globs from her asshole. But then her mouth went open and down on my cock shaft. Like a real trooper, she gave another great blow and suck job as she lapped my cock clean and swallowed all the residue. I could feel my balls begin to respond and tighten; I knew another load was starting to form. I patted her on the head and told her she was a good whore who was now used and abused. She smiled and asked if I would fuck her more before I left. I nodded yes; but neither of us knew what the evening would hold before it was over. Teen Age Gigolo Ch. 02 It was another Saturday; another day to earn some money by satisfying unfulfilled females. In all honesty, not all of them were unfulfilled intentionally. I had an 11:00 "service" appointment at the new high rise project. I pulled up to the Guard Station and confirmed I was there to see Mrs. Adams. I gave my name and indicated I had an appointment. He checked his clip board and confirmed I was expected. As he handed me a parking pass, he called up to her; confirmed I had arrived; and was on my way up. He directed me to the parking lot. I parked my car; and went into the lobby. I turned right to the elevators. I entered and pushed 15; she lived in Apartment 1501. She must have heard the elevator. She was standing at her door. She held up her finger to her lips as a sign to be quiet. She held the door further open and ushered me in. I introduced myself as Thomas and that I was there by appointment set up through Rose. She nodded her head in agreement and suggested we make ourselves comfortable. With that she led the way into the living room. I knew from Rose she was married; she and her husband had just moved into the apartment project after selling their house. The furnishings were lavish; and I complimented her on the tastefulness of her decor. Clearly, she was nervous. As we sat, I thanked her for the opportunity to visit with her. I assured her I was there for her pleasure. She should not be shy in letting me know what she wanted to do. I took her hand and kissed it lightly. I moved slightly closer; I knew now was the time to take it slow. Rose and I had agreed to allow an extra 60 minutes for this appointment. I always trusted Rose and her instincts. I noted she looked so tense; and there was no reason to be. With that, I stood and walked over to the slider to the balcony. I complimented her on the view. There was some light music playing in the background. I turned and began unbuttoning my shirt. Her eyes were riveted on me. I let it fall from my shoulders and asked if I might place it on the chair. She nodded; still she had not taken her eyes from me. I walked back to her and again assured her she should relax and enjoy herself. Was there anything she would like me to do in particular? She had a pondering look on her face as I turned. I went back across the room to the chair and slipped my shoes off. I began dancing to the music as I unbuttoned my shorts. I allowed them to fall and I stepped out of them. I was now wearing just a black silk thong. I walked back toward her; her eyes were now riveted on my cock area. I extended my hand and asked her if she would like to dance. At this point, allow me to describe her. Her full name was Diana Adams. I'm not certain what her maiden name was. I learned later she was 67. She was 5'7" and weighed in at about 170. From he waist up she appeared to be proportionate; from the waist down she had an oversized ass and what appeared to be thick thighs. I wondered if the weight was causing her some concern. Her hair was dyed blonde; and she had green eyes. She was wearing a silk blouse with contrasting slacks and heels. A gold choker necklace and 2 diamond rings were her jeweled adornments. She used heavy makeup and thick lipstick which I liked. Anyway, wearing just a thong and smile, I walked back to her on the sofa. I extended my hand and asked her for the dance. She blushed and smiled at that. Extending her hand, she rose and I led her onto the "dance" floor. The music was slow. I put my arm around her waist and held her close as we began dancing in the middle of the floor. I could feel some of the tension leaving her; but still there was something being held back. She had already pre-paid $200 for this session. I was whispering in her ear, as she rested her head on my shoulder. I stressed to her I was there for her pleasure; she should be quite explicit as to what she would like me to do. With that she opened up. Her husband was in the bedroom closet hoping to watch me fuck her. She was afraid I would leave. I assured her I would not leave as I began unbuttoning her blouse. I was kissing her neck as I did so and I knew she could feel my hard on. I had nothing but a thong on. She relaxed a bit more as I removed her blouse and laid it on the chair next to my clothes. We continued dancing and she was nibbling on my neck and running one of her hands across my back and down my ass cheeks. With one hand, I unsnapped her bra; that was a secret I had learned months prior. I backed up slightly and lowered it from her shoulders; it too went onto the chair with her blouse. She began crushing her titties against my chest. They were big and looked like they would have inch long nipples once I worked on them. We resumed dancing; and one of my hands fell to her ass and began squeezing. She was grinding into me now; and I began to unzip the rear of her slacks. I stopped as they began to fall; and told her to balance herself on my shoulders while she stepped out of them. She was down to heels and highcut black panties. As I helped her, my face went into her crotch and I could sense her juices were flowing from the aroma. I took the opportunity to kiss her through the panties. I think that got to her. I stood up and we resumed dancing. After a couple of minutes, I suggested we better let her husband out of the closet. She giggled. At that, I asked if she wanted me to use a rubber while we fucked. She shook her head no forcefully indicating she wanted to feel my juices flow into her. She also told me Rose had vouched for my health and virility. With that, she took me by the hand and led the way to the bedroom. As we walked down the hall, I suggested we tease her hubby a little to get his juices flowing. She agreed. His name was Jim and he was 77. I asked what he would be doing in the closet. She thought he might jerk his cock; more likely he would try to take a few pictures through the door crack. I asked if that was her wish. She nodded yes indicating she would like to be photographed with me. I stopped; went back to my clothes; put on my sunglasses; and returned. Pictures were no problem now. We continued into the bedroom and I stopped at a point where I knew he could see us. I began frenching her and rubbing her ass through her black panties. My other hand dropped down her front and was massaging her pussy. I could feel the wet spot; she was ready. Or at least that was her thought. I stopped; walked over to the closet and opened the door. These stood Jim with a camera. I told him Diana wanted to be photgraphed; so he might as well come out of the closet and do so. With that, he went back into the closet and came out with a cam-corder. Smiling like a cheshire cat, he said let the action begin. I took Diana by the hand and led her to the bed. I turned to the camera and introduced her and I to the camera; and noted James was the camera man. With that, I turned back to her and began frenching Diana in earnest. Apparently she had never been kissed so ardently as she had to come up for air on more than one occassion. My toung was driving deep into her mouth and she responded in kind. I lifted her and lay her on the edge of the bed. I peeled her panties down over her hips and she lifted up her ass so I could work them to her ankles. I tossed them to James when I pulled them from her ankles. Still wearing a thong, I wnet down between her legs and began eating her pussy. That was a sure way to bring out the whore in a woman. She had extremely well developed pussy lips and a clit which was about half an inch long. I had my own unique technique. As I sucked hard on both pussy lips, my tongue was driving on and off the clit. It worked with Diana. My tongue was causing her to spasm one hit after another. I did not think older women could cum so much; perhaps she was the exception to the rule. Her legs were across my shoulders and down my back as I continued eating her pussy. I noticed James move in with the camera. I lifted my face enough he could get a good shot of her pussy and the fluids she was shooting out. I moved her finger down to her clit as I stood. I stepped from my thong; and as requested I turned to give James a good view of my goods. I pulled Diana a little further to the edge of the bed as I stepped between her legs. Her pussy was so lubricated my cock slid right in to the hilt. Truth was she was a bit loose; definitely not a tight pussy. But the customer was always right; I did my best to create the impression she was tight. Don't get me wrong; her pussy felt good. It just was not tight. She had a thick bush and it was evident she was not a blonde. I started slapping my cock in and out of her. I had enough force she could feel my balls slapping against her ass cheeks. Her jiggling belly was a bit of a turn off. But the customer was always right. I fucked her for 15 minutes or so when I raised her legs onto my shoulder blades a bit higher. Her juices had been running down to her asshole and my cock was slick with her cum. I pulled out and let the head of my cock drop to her asshole. I pushed forward and in it went. She'd been fucked in the asshole before or she did dumps the size of bricks. Now I was fucking her good. Another 15 minutes of ass pounding and I could feel my load cumming on. Her eyes were closed as she concentrated on every thrust of my cock. I could feel James behind me getting some good footage of my cock in her ass. I asked her where she wanted me to dump my load. I thought she would want it in the pussy. But James piped up he would like to see it all over her face; he thought it might even help her complexion. She nodded her head in agreement. I finally pulled my cock free and held the base tight as I walked around to get up to her face. I'd been fucking her long enough, my balls were bloated with cum. I stood beside her face and began to jerk my cock off. My cum spurt forth; I think I gave her 9 good shots on her face. James moved in with the camers and got some more great footage of her lightly massaging my cum into her skin. Then the weirdest thing happened. James put down the cam-corder and began licking my cum from her face. Amazing. I was standing there holding my cock with every intention of sliding it into her mouth for a clean up. But watching him do that made my balls tighten and hardened my cock. I hoped I wasn't turning gay. I went back down and hefted her thighs onto my shoulders as I slid my cock back into her asshole. She didn't resist and began smiling when she felt my thrusts begin. I did not use tenderness or concern this time. I figured after him sucking my cum off her face, she should get fucked good. I did. She was screaming lightly as I fucked her hard in the ass. My balls were beating on the bed as I slammed my dick into her anus. I was holding both ass cheeks as I drove deep in and out. I dug my finger tips into her flesh when I felt another load build up. She knew I was cumming by the look of concentration on my face. It felt so good to shoot that load deep into her asshole. This time when I extracted my cock, it had cum and brown gobs on it. I gave her no choice as I lifted her head and pushed my cock into her mouth. She opened wider and wrapped her lips around my shaft. She sucked it clean. I helped her from the bed; and we left James looking at the puddle where she'd been laying. Who knew what his intentions were. Mine was to get a shower and ensure she would be back for more. Mission accomplished. As she washed my cock and balls, she indicated I was even better than Rose had told her. She wanted to know if I would come back. She wanted to know if they could show the video to friends. As I toweled off, I suggested a screening party with she and I as the center of attention. She smiled in concuramce. I stopped in the bedroom, before departing, to retrieve my thong. I went out to the living room and began to dress. James came over and thanked me for the performance and asked how to schedule a follow up. I confirmed his wife knew and we should limit that knowledge. He didn't look too happy; he still gave me a $50 tip. We shook hands as I exited and headed for the elevator.