"What do you mean?" I asked Charlie's friend in disbelief. "Are you saying you will pay me to have sex with some of your lady friends? Uhhh , are you serious?" It seemed like I was entering someone else's fantasy. This would certainly beat the hell out a real 9 to 5 job at the hardware store, or mowing yards all summer I thought. I was nearly twenty-one, was going to college and living the good life. It wasn't like I was starved for affection, but I admit to wandering in and out of short term relationships like they were stores at the mall. The girls I dated weren't boring by any means, it's just that I was so easily distracted by anything beautiful in a skirt. All of this peace, love and 'free sex' stuff was my motto up until I met Gypsy, a good friend of my friend Charlie. Charlie was a bass guitarist at a popular Houston night club and ran around with a gorgeous hot blond named Jan. In their prime, his band was a very good band and they opened for some of the biggest headliners of the 60s and 70s. Charlie was about 10 years older than me and took care of me like he would a younger brother. If Charlie hadn't been such a nice guy, I swear, I would have banged Jan for sure. Jan and I often sat together and drank while we listened to Charlie's band. Most of the time during sets, we hit the dance floor together. Charlie didn't mind Jan and me dancing because he knew I could, and would take care of Jan if need be. Jan, on the other hand, took great delight getting me rock hard on the dance floor just to leave me stranded. One night after several in our group closed down the club, Charlie and Jan asked me if I wanted to meet one of their friends. Charlie told me she went by the name Gypsy Savage and was in her mid forties. I've always preferred women a few years older than me, but this was a bit beyond my age preference, but a friend of Charlies is a friend of mine, so I agreed. So we piled in my BMW and headed to Gypsy's house a few miles away. "Gypsy is a free spirit my friend." Charlie blurted. "But don't let that fool you. She is a brilliant business woman who just happens to be very hot. Take care of her and I promise you Howdy, she will take very good care of you." he added with a broad grin. We pulled into Gypsy's long driveway about 3 am. According to Charlie, Gypsy's husband died from injuries suffered in a horrible accident a couple of years earlier, and she had recently been awarded a massive insurance settlement. So Gypsy now had the luxury to pursue whatever pleased her. As Led Zeppelin's Stairway to Heaven blared away inside, the distinctive aroma of a highly popular medicinal herb drifted from the back door into the four car port-e-cache. Gypsy stood swaying in the doorway and was wearing nothing but a floor length semi-shear nightgown and a big smile. The warm glow of interior lighting behind her silhouetted her shapely figure. Gypsy may have been in her mid 40s, but she was beautiful and still had the body of a much younger woman. She was just over five foot tall, big brown eyes, long curly brown hair, and had a smoking hot body. After making a hasty introduction, it didn't take Charlie and Jan long to excuse themselves to the back bedroom, leaving me to the lustful escort care of Gypsy. She offered me a puff off of herhand rolled fattybut I declined, so she poured us both a shot of Tequila. After three shooters, she was out of her gown and rubbing her luscious body all over me as we kissed. A few short minutes later, she had my pants around my ankles and she sucking at my throbbing cock. Gypsy sucked at my cock until I delivered a hot stream of cum into her open mouth. Then she pushed me backwards onto the couch in the living room and straddled me. She rubbed her small firm tits back and forth in my face as I took turns sucking each hard nipple. Gypsy was so wet she slid her tight little pussy all the way down on my throbbing cock with one hard push. She was in such a mellow state that we fucked for over an hour before she came in a very vocal, body shaking orgasm that soaked me and the couch. I couldn't believe what a tight pussy this forty something year old woman had. I don't know what I was expecting, but it wasn't this. We collapsed onto the couch laying side by side facing each other. "Howdy" Gypsy started, followed by a deep drag on her hand rolled smoke, then a long pause. She studied my face as she held her breath. Then as she exhaled slowly, she whispered , "Have you ever thought about renting that nice big cock of yours to women like me? You know, slightly older women whose hubby isdead or dead in the bed. You know what I mean man, the kind who care more about making money than making love to their woman?" The haze in the room made it easy to laugh at such a thought. "What do you mean Gypsy? You're kidding me right?" Gypsy smiled and squinted at me through glassy eyes. Then with a deep soulful giggle, she patted my face and said. "I'm as serious as a satisfied high- dee -ho can be. I'll be your business manager and handle all the appointments for you. All you have to do is show up on time at whatever address I give you, and then do whatever that lady wants you to do for her. Are you game Honey?" Gypsy continued as she slowly exhaled another smokey giggle. "I'm serious Howdy. You will get all the pussy and ass you will ever want. And you and I will make a small fortune. Of course, you will be expected to fuck yourpartner on a regular basis." "Do I get paid overtime for fucking my partner?" I laughed. I marveled at the notion that a beautiful woman would actually pay for a guy to fuck her, but there was no reluctance in my desire to plant my cock in as many of those horny old hot pussies as I could. So, just like that, we were in business. "Okay Gypsy. Let's do this. We have nothing to lose, right?" I extended my hand to consummate the agreement, but she insisted that if we were going to shake anything, it would be her ass on my cock. We fell asleep at some point during the wee hours of the morning and slept until after noon. The smell of breakfast and coffee permeated the room and I was starving. "Get up partner." Gypsy said, you have work to do, giving me a pat on my naked butt. Gypsy had on a pair of very short cutoffs that only covered the top two thirds of her tanned ass cheeks and a shear tank top that left nothing to the imagination."Grab escort bayan a quick shower partner while I finish making you breakfast. You're going to need your strength today." Over breakfast, Gypsy shared her plan of our partnership with Charlie. Charlie and Jan thought the notion of a woman actually paying me, their friend Howdy, for cock was hysterical and busted out laughing. It sounded funny to me too and I joined the laughter. Gypsy looked Charlie square in the eyes with a poker faced stare and asked, "Charlie, has Howdy ever had his big fat cock in YOUR pussy? It's money in the bank baby, and we are gonna cash in." Then her expression turned towards Jan and echoed the same question of her. Jan giggled a big smile, shrugged her shoulders and said, "No, not yet." I was happy at the thought of getting paid to do what I would have gladly done for free. They could laugh all they wanted as far as I was concerned. All my buddies had to beg their girlfriends for any sexual favors and then worry about their girlfriends daddies finding out. And here I was about to get paid for those same services. As we sat having breakfast, Gypsy's home phone rang. "Hello Barb." she said cheerfully to one of her girlfriends. "Thanks for calling me back. Do you remember a conversation you, the girls and I had a few weeks ago? You know, THAT conversation? Well, I have just the right person to fill that order for you. Uh, no Barb, he doesn't work pro bono ! But I promise, you will love his nice thick hard ' bono ' though, Just don't expect it to be free. Barb honey, it doesn't matter how attractive you are dear, he is working his way through college and you are going to help him out. Agreed? I'm giving him your address and you make sure to give this nice young man a crisp new Benjamin or two when he's through. Muahs ...Love you." Gypsy hung up the phone and smirked a 'I told you so' towards Charlie and Jan. Then she turned to me with a huge smile, "Okay partner, we're officially in business. Here is Barb's address. Be there at 3 this afternoon. She is a wild one, so don't let her intimidate you Hun . Call me from her house after you are done and have showered. I will have you another client for early evening, say, 6 ish. After you are through with your late afternoon call,meet meback here." I remember being unsure of the whole notion of becoming a male hooker. I had always been the one on the prowl, the aggressor by nature. I enjoyed the hunt and the capture for sure. Now, I was having the tables turned on me. But hey, getting pussy is getting pussy. Now, this woman I met less than 24 hours ago, was farming me out for stud services to her friends. Oh well, the money sounded too damn good to refuse, and now, there was no way to gracefully bow out. Even though I had a relatively nice car, it was totally out classed in Barb's neighborhood. She lived in a gated community long before gated neighborhoods were fashionable. The guard at the front gate looked at me with a suspicious eye as I asked for directions. "Are you one of Barb's son's friends?" he asked as he raised one eyebrow. "Honestly sir, I don't know if Barb even has a son. I'm here to see her bayan escort about some personal business Sir." I answered in a wavering voice. "Good answer kid," he said drumming his fingers on the side of his holster. "Barb doesn't have any sons. In fact, she doesn't have any kids period." he added. Then he took a step back from my car, and lightening up a bit, he offered directions as the massive front gate rolled to the side. Every lawn in the neighborhood was manicured to perfection. This place was like nothing I had ever seen. Each mansion sat on a few landscaped acres and was uniquely spectacular. It seemed like every mansion had a gang of workers in the yard doing something. I pulled my little Bravarian red rocket up in front of the most beautiful mansion I had ever seen. In the long sweeping circular drive out front was a new black Silver Cloud and a red Ferrari. "Whatever it is her husband does, I wanna do it too." I mumbled to myself. I felt a bit awkward and out of place, but I had a job to do, and I was going to make it happen. My mind was made up and I was determined to make this Barb woman the happiest woman on her street. I can do this I said to myself, attempting to bolster my confidence as I walked towards the large front door. The door bell rang like church bells echoing through empty cobble stoned streets. Without being too obvious, I peered through the eight foot tall leaded glass doors into the large entry . I could see all the way through the house, and past enormous plate glass windows into the pool area in the back yard. As I reached for the bell again, an older man in a black suit and tie opened the door. "May I help you young man?" the finely tailored gentleman asked in his best stuffy voice. "I'm here to see Barb." I said, extending my hand to shake his. Without flinching, he glanced downward at my extended hand and rolled his eyes. "Follow me Sir. What is your name so I can properly introduce you to the Lady of the house?" "Howdy." I replied. He stopped and briefly, looking over his half turned shoulder at me in disbelief, "Howdy is a crude form of salutation Sir, not a name." "Howdy!" I heard a chirpy youthful voice call as my name echoed off the rich cherry wood paneled walls. "Is that you?" Barb came walking briskly around the corner. "Howdy, it is so good to meet you. I have heard glowing reviews about your work. I can't wait to find out for myself." she said as her eyes gave me a quick me up and down several times. In classic form, Barb took both my hands in hers, lifted one foot to knee level behind her as she leaned into me and pecked a kiss to each of my cheeks. Barb was a stunning woman in her late 40s or early 50s. She had piercing green eyes, coal black hair, beautiful thin lips and long shapely legs that were accentuated by the 4 inch heels she wore. In contrast to Gypsy's dark tan, Barb had almost no tan whatsoever. Like Gypsy though, she had a beautiful shape for a mature woman. Her very presence exuded refinement and confidence, plus she wore an intoxicating perfume that I couldn't get enough of. Her lustful hungry smile turned professional in the blink of an eye as she turned and politely excused the elderly gentleman who had answered the door. She slipped her hand between my chest and upper arm, and squeezed my bicep as she invited me into the great room. "Howdy, I am so happy you had time to see me with such short notice. May I pour you a drink? You are old enough to drink, right Howdy?" Barb teased with a smile.