0 comments/ 35625 views/ 4 favorites A Gigolo's New Encounter By: dark_knight33 I hire out from time to time to a dating service. The clients are for the most part are 40+, and a tad on the bulky side. The women call a dating service for a number of reasons, some of which are, single, lonely and don't do the bar scene, or husband has lost interest and they desire sex so they slip into a motel while the husband is working or it makes them feel young and attractive yet because they have caused the date to orgasm. Some are recent divorcees and desire to experience what sex might be like when they go out for the first date after years with the same dull dude. Very seldom is there a shock when I show up because the agency always asks the wish list or the desires of the client to insure the client gets what she is paying for, which will lead to future request if all goes well. For the particular request that I am going to expound on, there was a mix up. I have never taken the time to determine why or where because it ended very well for the client and me. Most of the times it's a job and a week later that woman has long faded from my brain. However, this particular date made an everlasting impression. I will remember it forever. I arrived at the designated time in a plush downtown hotel meaning money. I called the room from the house phone and announced that I was in the lobby. I heard, "Please come up John, I have been expecting you." When I arrived at her room, the door was slightly ajar. Many times, I find this. The occupier does not desire to draw attention from the adjacent rooms with a knock. I gave a light tap and the door opened. Gladys was standing behind it because no one was there when it opened. I stepped in and as the door was closing behind me, I heard, "Oh my God there's been a mistake." I turned and saw the most beautiful, thirty plus woman I have ever seen in my life. She was in a light blue, mid-thigh, robe. She had the legs of a twenty year old, at least the part that was visible. She had jet-black hair, straight to her shoulder blades, looking so silky and shiny; not a dry frayed end in sight. Her eyes were the most stunning blue I had ever seen. Her skin was slightly olive. I made an assumption, that her ancestry was gypsy and if correct, she would be a wild animal in bed from the stories I have heard from friends. "I'm sorry a mistake? You are Gladys are you not?" "Yes but I was NOT expecting..." I interrupted her with, "A black man." "Yes, I'm sorry. Can you please leave?" "Sure, I will call the agency and arrange a replacement but may I ask you some questions first out of curiosity on my part. I have never had the experience in my work to encounter such a beautiful, majestic looking woman. You are truly the most beautiful in my five years of service that I have seen and met. It is non of my business but with that body and beautiful face why pay when there are maybe twenty guys down in the bar that would be more than happy to take care of your needs." "Young man let me set you straight and educate you a little bit. I'm sorry, I am being rude. It is not your fault that the agency screwed up. I should not be taking my disappointment out on you. I am rude. Would you like to share this bottle of wine with me while I answer your inquiry?" It was obvious from the slight slur and body movements she had some wine earlier to settle nerves for medicinal reasons. "That would be very nice, thank you Gladys. I am young and life intrigues me. Here you are so beautiful and using a dating service, why?" She handed me the glass of wine and asked me to sit on the sofa. She sat opposite of me in a huge chair. I was discreet and did not look often at her lovely thighs but assumed that if I could get a drink or two more into her, she might accidentally give me a freebee show. "John, look, what you say about getting guys is true. Let me first say I am single, a career woman and have no interest in marrying a mommas' boy. The guys downstairs desire to get into my pants for their benefit, not mine, others fall in love and want to marry. Others lie and are married but cheat, it goes on and on." "May I top off your wine Gladys?" "Why thank you John that is very thought full and considerate of you." "So John I am here on a business trip and have tomorrow morning free. I thought I would hire company and if I slept in late, it would be okay. "Look I have never hired a service before. I have no knowledge of this sort of activity. I am nervous. Normally I am in total self-control. In addition, I have heard stories about you black guys, particularly in regards to the equipment you posses. Please understand that I do not have anything against your color. As a matter of fact, you are a strikingly handsome as well as good looking virile young man." "Thank you Gladys. Too bad, you cannot see me blushing." Gladys developed a nice smile and giggled at my comment. "May I refill your glass, Gladys?" "Oh thank you John, You are quite observant and a gentleman." "Thank you Gladys" "John before making the call may I ask you a question or two?" "Sure Gladys, be my guest. I have all the time in the world to share with such beauty. The longer I can stay and talk the happier I will be." "Does the service provide you with many customers, John?" "Yes it does Gladys. I could be on the go 24/7 if I desired. The service has ten black men from twenty-five to fifty-five years of age. The ages covers 90% of the request." Gladys stood and changed out her legs. She had her left leg under her and now it was her right leg. I did get a glimpse of a dark patch when she reached to cover the void between her thighs with the robe. Gladys began to inquisition me about numerous things. I decided now that she was loose from the wine I would be a little bolder. "Gladys, could I ask a favor" "Sure John, what is it." "Might you consider sitting her on the sofa with me? You are over there and it would be much more personal if you could be nearer." "Sure John, you are right. This does seem too formal." When Gladys had seated herself, my eyes roamed to her breasts. The robe had opened slightly and the view was stirring my hormone. It appeared she had perfect breasts. "Is it a rumor or fact about the tool of a black man?" "I assume you mean cock, Gladys," "Yes, John your ...." "Say it Gladys, we are adults." "Cock!" "You know Gladys white guys have them, also. Now that was not so difficult was it?" I saw her smile. "Gladys, it is the same for black and white. There is an average and then the extremes. On average the black man has one inch on white guys but more of them are over average." "Go ahead Gladys. I know you want to know." "Know what, John?" "What we have been talking about, lengths of a black man's cock." "I know you want to know. Ask me." "How long is yours John?" "My what, Gladys?" "You don't give in or up do you John? Your cock, how long is your cock? There does that make you happy?" "Yes it does Gladys, very happy." "John, do you have a girl friend?" "Yes Gladys, I do." "Is she white or black?" "She is black, Gladys." "Do you ever go out on dates with white girls?" "Occasionally, Gladys. The white girls that will accept an invitation have experienced black before and need to do it again and the others are curious for the first time. Some I would have loved to have gotten more serious with but they were just interested in a one-night thing." "John, do you find a difference between the races?" "I'm not understanding the question Gladys. Can you please rephrase it?" "Well you know when you are in bed with them and having sex, is there a difference." "Different in what regard Gladys? Each woman in bed is different." I decided the wine had her toasty so I put my right hand on her exposed right knee and was making soft circles. "God John you are making it hard for me. I mean when you are in them does it feel any different?" "Gladys in all races there is very tight, tight, normal, a little loose, and very loose. So I never know until I get there. But I love tight, the tighter the better." I made sure my hand had moved up her thigh a tad jut to above the knee. "How old are you John?" "I'm thirty-three Gladys." "I wish I was your age again." "You are not much older than me. I am guessing maybe thirty-five." Gladys jerked and spilled her wine from starting a laugh. She uttered, "Damn I spilled good wine over that ridiculous comment." "Let's not waste good wine." I buried my head into her cleavage where most of it went and made slurping sounds as I was sucking it up. I began low below her cleavage. I worked my way up slowly waiting for a move on her part. I was surprised that I had reached the top of her cleavage without her asking me to stop. When my mouth reached the top of her cleavage, I began with soft kisses. I proceeded working my way to her neck. I heard her breathing rate increase. I worked my way to the side of her neck and back to her ear. I then lightly kissed her ear and whispered, "God Gladys you perfume is awesome to inhale. I could sniff it all night." Gladys placed a hand on the top of my shaved head and applied light pressure indicating to go down. I began kissing downwards and took aim for her left breast. The closer I was getting to her breast, the lighter the pressure became on my head. I knew if I did everything right this lady will want my friends and me a lot when she came to town. I used a free hand to move her robe off the breast. I could then give it the tender, loving care it desired. I was kissing it all over, sides, top, bottom, but not the nipple. I avoided it on purpose. I then began to kiss my way over to her right breast. Her breathing was becoming more shallow and desperate. I gave the right breast the same treatment. I sensed some hip humping. She must have wanted her mound to rub against my body to get a little feeling there. I then made a point with my tongue tip and was dragging it all over her right breast. Her hand went to the side of my face to guide me to the nipple. When I felt my tongue touch the areola, I made circles around the nipple but concentrated the tip of my tongue on the areola. Moans were emitting from her lips. I decided before I attacked the other breast that I would give her right breast the full treatment. I opened my lips to suck the nipple into my mouth, flicked it fast with my tongue, placed my hand under the breast and then bit lightly on the hard nub. She groaned like a guy coming and her body must have had an orgasm, from the panting and shaking. I acted as if nothing unusual had happened and moved back to her left breast. I gave it the same treatment as I had done on the right breast and she had the same physical reaction when my teeth sank into the nipple. I placed both hands on top of her breast covering them until she calmed a little but was dragging the pointed tongue to her naval. Upon reaching it, I drilled and licked it with my tongue and even sucked on it. Gladys moaned and placed her hands onto the sides of my face and was pushing down, sending me the message to eat her. My jaw was opening the robe as it was moving lower and lower. My jaw then touch very sort pubic hair. It was jet black. I drug my tongue all over her mound, the edges and lightly up and down the gash. Her hand pressure was intensifying to position my tongue at her clit. I stabbed my tongue into the gash and drew it up from the bottom. When it touched the clit, I flicked it with fast flicks. Gladys arched and moaned. I jabbed two fingers into her pussy, at the same time sucking her clit into my mouth. She went to riding my fingers and moaning. I lifted my face and looked at her and she screamed, "No Don't stop now, finish it." "Finished what Gladys?" "Finish eating me to a cum." "Show me how bad you want me to finish you. Play with your tits." "I have never done that and let someone watch." "I began a slow withdraw of my fingers and saw and heard, "Okay, okay, I will do it. Please eat me, Oh God I need to cum again. I have never been so turned on and hot. Oh John please." I was finger fucking her slowly, used my thumb from the free hand and massaged her clit as she was playing with her tits. It was a wonderful scene. She was in her own world now. Her mouth was open and she was panting and humping. I was careful not to get her to where she would orgasm. When I felt her pussy walls clamp for more friction I withdrew them. Her eyes shot open followed with, "Oh God John, finish me please, I did what you asked me to do, Oh God, John please." She was almost in tears. "In good time you hot bitch in good time." I stood and removed my clothing deliberately slow. She was twisting and pulling her nipples and humping to an imaginary cock. Her head was tossing side to side but her eyes stayed focused on my cock. When I was down to my g-string, I massaged my pouch letting the anxiety build in her. "God John take it out and do me with it. I need it." "What do you need Gladys?" "Your cock John. I need your cock." "What do you want my cock to do bitch?" I knew I was pressing my luck but previous experience had taught me a woman at this point is out of it and only focused on getting relief. "I want your cock to fuck me John." "What color is my cock, Gladys?" "It's black, you know that." I walked in close and jammed two fingers back into her. She arched and I with drew them at the same time. "Tell me again bitch what you want." "I want your cock to fuck me, please John, make it make me cum." "You want this black cock to fuck you Gladys?" She still had not seen it. I turned my back and tugged the g-string down. I turned to face her and her mouth opened with an expression of panic. "Tell me again what you want bitch." "I, I, I want that black cock to fuck me." I walked up to her and replaced the fingers to refresh her memory while waving the monster around. "Oh John, please, please, please stick it in me." "Tell John how much you want it, bitch." "Oh John get me off and I will do anything you ask of me. I just need your black cock deep in me, giving me your love juices. I have lots of love juice for you." "You are saying you are open for anything?" "Yes John you have me so horny. I have never been this way before with any man. Oh John, your making it build more and more. I don't know how much more I can take of this torture." "Okay bitch, get on your knees on the sofa and give me a good view of that thing where you desire this black cock of mine. I don't want you to disturb the neighbors so I am going to place a gag in your mouth just in case you are carried away. Most women do the first time, you kno. Is that okay Gladys?" "God anything John just send me to Pleasureville with that black cock of yours." I let her place the ball in her mouth and then I secured it. "Lovely butt you have Gladys. Both your ass and pussy are so beautiful to be looking at." I was running my hands all over her butt cheeks and would dip into her leaking cavern for juice to lube myself good and her crack from pussy to her waste line. I was finger fucking her more and more. She began to moan nicely and thrust to get more fingers deeper into her. "Play with your tits bitch and get your self hot, as hot as you can." I was watching carefully her progress. She went to nipple pulling and moaning. I placed one foot on the sofa, and when I thought she close to the edge, I placed a hand on her left shoulder, removed my fingers from her pussy, placed them on my cock and shoved my cock into her hot cavern, which elicited a, "Mmmmmmmm," along with a back arch. I thrust deep so ever nerve in there new something new was there. After two slow, deep penetrations, I felt her pussy walls grip my cock. I removed my cock and quickly placed it at the other hole, pushing the head in with pulling her back with my left hand, which was on her shoulder and using my right hand on her hipbone. She had already gone into her orgasm on my withdraw, so the intrusion into her virgin hole was a new dimension to what her body was experiencing. The intrusion of my cock into her virgin orifice, made her arch even more so and with an intense, "MMMMMMMMMMMM," into the gag from both the pain and the orgasm. Her body reacted as if she was having an epileptic fit. The moans and color of her skin going red, the perspiration appearing on the nice toned skin, told me she was some place she had never been before. She was snorting for air because of the ball gag. Her long beautiful hair was flying all over the place as she shook her head. As more perspiration collected on her body, more of that hair was clinging to her skin. Her head then came to a rest on the top portion of the back of the sofa. I did not fire. I let her calm a little, keeping very light pressure on her clit where I had placed my hand midway into her cum. It took awhile but she was making movements to feel the cock in her ass and more clit massage. I let her set the tempo. The faster she was humping the more and faster I was massaging her clit. I did not hump much into her ass. She got what she would push back on. I sensed she was close to a cum. I undid the ball gag, pulled slowly from her ass and plowed deep into her pussy while flicking the clit fast and furious. She arched and only uttered "Ahhhhh," as she collapsed with her arms hanging from her shoulders, dropping, her mouth open, panting and saliva running out. Her body seemed to be in a constant orgasm as I kept flexing my cock, letting her pussy know it was there. I heard a whisper, "Enough John God take it out. My body is shot." "Okay bitch but what about me. I still have all of my precious black man love juice for you." "Oh John, do whatever makes you feel good. I'm spent." I placed my hands on her hipbones and gave her pussy the royal treatment. She was still limp as a wet rag but still managed to moan, "Ohhhooo...Ohoooo...Ohhhh," with ever inward thrust. I started slow. This bitch was tight. I was going to make it last because I will never have a women her age as tight again. The tightness was getting to me as if she was eighteen. I wanted to slow down but my hormones would not let me. I heard her panting as I was burying it deep, holding onto her hipbones. I felt my balls pull up. I pulled out and plowed into the tighter hole just with my head. She let out with, "OOOOOOhhhhooooooooo, God." "I let out with "Ahhhhhhhhhhh," as I made the deposit she requested. Her having another orgasm shocked me. I collapsed onto her back panting. After sensing we were breathing almost normal, I heard, "John can we do this in the morning again and then again tomorrow night?" My eyes popped open and quickly I said, "It would please me very much babe. You are an awesome lady." Gladys then said, "Let's take a quick shower and get some sleep and rest so we can play again." I pulled out slowly from her ass and as she turned to get off the sofa, lifted her and carried her to the shower. She lowered her head on my shoulder, placed herself on my chest and said, "God you are sweet. Where are guys like you hiding?" While showering we did some soft lip kissing, scrubbed each other, dried each other and hit the bed. I spooned into her and placed a hand on a breast. She placed her hand on top of mine. The morning play was out of this world. A Gigolo's New Encounter. I hire out from time to time to a dating service. The clients are for the most part 40+, and a tad on the bulky side. I am a 30+ year old guy, divorced, well toned, 6 foot, 185 pounds, with blue eyes and curly blond hair. I have sparse body hair and I make sure my jewel sack is smooth for the ladies, and keep the rest well trimmed so that toothpicks are not left behind in their sweet mouths. I have a regular office job as an electrical engineer and with this moon lighting job I meet a lot of different women which keeps my juices flowing, being paid, and do not have to do the bar scene that often. The women call a dating service for any number of reasons, some of which are: being single and lonely and do not do the bar scene, or the husband has lost interest and they desire sex so they slip into a motel while the husband is working. It makes them feel young and attractive yet because they have caused the date to orgasm. Some are recent divorcees and desire to experience what sex might be like when they go out for the first date after years with the same dull dude. Very seldom is there a shock when I show up because the agency always asks the wish list or the desires of the client to insure the client gets what she is paying for, which will lead to future request if all goes well. For the particular request that I am going to expound on, there was a real shocker. The request was not unusual. There were two ladies each desiring a guy but desired to switch off and on in other words a four some for the night. The other guy was to have the same body structure as me but brown eyes and black hair. I went with Rob whom I have gone out with on-call before. We both have worked for the escort agency about three years, joining about the same time. By the way, I am Rich. When we arrived at the motel, we called the room and announced we were in the parking lot. Rob placed the call, then turned to me, and said, "They are ready for us and just to walk in, the door will be open." When we arrived at the room, the door was slightly ajar as Rob indicated it would be. Many times, I find this. The occupier does not desire to draw attention from the adjacent rooms with a knock. I gave a light tap and the door opened. My eyes saw the most beautiful, thirty plus woman I have ever seen in my life. She was in a light blue, mid-thigh, robe. She had the legs of a twenty year old, at least the part that was visible. She had jet-black hair, straight to her shoulder blades, looking so silky and shiny; not a dry frayed end in sight. Her eyes were the most stunning blue I had ever seen. Her skin was slightly olive. I made an assumption, that her ancestry was gypsy and if correct, she would be a wild animal in bed from the stories I have heard from friends. "Hi fellows, I'm Gladys." "Hi Gladys, I'm Rich and this is Rob. Thanks for calling the agency and we will try our best to take care of your needs. I assume Jill is putting on the finishing touches since I hear the hair blower." "Yes she is. Look guys, this is her first time to do this and she is a little scared. She is going through a divorce and I talked her into relieving some of the strain and pressure for a few hours by doing what I do. She agreed if we could be together that is why the request for two of you. I told her she needed to play at the same time." Rob said, "Thanks for filling us in; that helps out a lot." Gladys said, "That's why she is still prepping. I wanted to chat with you two first so you will understand her shyness. Care for a drink? I travel with a mini-bar over there, help yourself." "Gladys may I ask you some questions first out of curiosity on my part. I have never had the experience in my work to encounter such a beautiful, majestic looking woman. You are truly the most beautiful in my three years of service that I have seen and met. It is non of my business but with that body and beautiful face why pay when there are maybe twenty guys down in the bar that would be more than happy to take care of your needs." "Rich, would you like to share this bottle of wine with me while I answer your inquiry?" It was obvious from the slight slur and body movements she had some wine earlier to settle nerves for medicinal reasons. "That would be very nice, thank you Gladys. I am young and life intrigues me. Here you are so beautiful and using a dating service, why?" She handed me the glass of wine and asked me to sit on the sofa. She sat opposite of me in that huge chair. I was discreet and did not look often at her lovely thighs but assumed that if I could get a drink or two more into her, she might accidentally give me a freebee show. "Rich, look, what you say about getting guys is true. Let me first say I am single, a career woman and have no interest in marrying a mommas' boy. The guys downstairs desire to get into my pants for their benefit, not mine, others fall in love and want to marry. Others lie and are married but cheat, it goes on and on." "May I top off your wine Gladys?" "Why thank you Rich that is very thought full and considerate of you." "Thank you Gladys" "Rich may I ask you a question or two?" "Sure Gladys, be my guest. I have all the time in the world to share with such beauty. The longer I can stay and talk the happier I will be." "Does the service provide you with many customers, John?" "Yes it does Gladys. I could be on the go 24/7 if I desired. The service has ten black men from twenty-five to fifty-five years of age as well as 15 white guys in the same age span. The ages covers 90% of the request." Gladys stood and changed out her legs. She had her left leg under her and now it was her right leg. I did get a glimpse of a dark patch when she reached to cover the void between her thighs with the robe. Then the bathroom door opened. I froze, my mouth went dry, my eyes bugged, I panicked with a fast heartbeat when I saw Jill; her hand went to her mouth as she turned to head back into the bathroom. I sat in shock until Gladys said, "My God Rich what was that all about? You are white as a ghost and Jill had a shocked look and ran back into the bathroom." "Yeah buddy, is she your ex-girl friend or ex-wife?" I managed, "Sister!" Both Gladys and Rob went, "Wow." My mine was going so fast over all sorts of crap. My heart was beating a mile a minute and I froze over the situation. My next recollection was Gladys lowering herself into my lap and sitting there smiling into my face. God she was beautiful. Her finger ran over my lips and I heard, "When you were younger did you play with yourself and have your sister on your mind?" I turned red not from being angry but embarrassed that I did have those thoughts and I was not going to lie I did not. I then heard, "Let me ask Jill if she ever thought of you that way. Look if she did then both of you can get your wish and fantasy tonight. That is why we are here. It might open a new outlet for you and her. Is that okay with you Rich?" Before I answered her, the thought of not wanting the night to end because I wanted Gladys so much and hoping it would lead to other nights, the thoughts of watching Rob doing my sister, me doing my sister, were overwhelming me. I heard, "I understand Rich stay cool while I talked with her." I did not have a chance to answer, Gladys headed to the bathroom. Rob came up to me and said, "Rich I can bug out. This is weird. I hope you have fun and get it on with your sister." "Look Rob, Jill is free. I'm not her guardian. Let's let her make the decisions. I want to do both. Gladys looks hot and damn I'm hard thinking of getting it on with Jill maybe." Rob and I talked about other things while Gladys was chatting with Jill. My heart stopped when Jill and Gladys came from the bathroom. Jill came up to me and we just hugged not saying a word. We stood holding each other tightly. I heard Gladys ask the front desk if there was another room available. I then heard her say, "Great!" "Look guys, Rob can go to the front desk and get a key for another room. He and I will go there and play. You two call when you are ready to swap. Jill can go to Rob and I will come to you Rich. Then the next switch is for you Rich to go to your sister and spend the rest of the night with your sister and me with Rob. In the morning we will get it on again all together if everyone buys into this." Rob and I looked at each other, shrugged our shoulders and nodded our heads in agreement. Gladys noticed and said, "Okay Rob lets let Jill and her brother get to know each other better while you and I have fun." Jill and I broke our hug after they left and looked each other in the eyes with tears as we went to kiss each other. It was obvious from the kiss that we desired each other like our first time to go all the way with someone. We undressed each other as we were kissing. Jill was standing in her black bra and bikini panties, with me in my silk boxer shorts when we broke the kissing action. My sister has blond hair like myself, stands 5 foot seven inches, with legs that do not stop. Her breasts are 34C with a waist of 26 and hips of 35 inches, which are perfect globes. Her hair is straight to the shoulder, so silky smooth with no frayed ends. When she wears it in a ponytail, she looks so hot. She weighs in at 127 pounds. Jill's soon to be ex, is a jerk for having a fling with Jill's best friend or was until she caught them together in bed. Jill knew what she wanted and she knew what I wanted from the boner that had been pushing onto her stomach and the tent of my boxer. We went back to French kissing. She then pulled her right hand off my shoulder, slid it down my chest and to the opening of my boxer shorts, stroked the pole that was rigid just for her. Jill had been feeling cocks since she was 15 so was an expert after 10 years. My hands in the mean time cupped her luscious boobs in the bra that soon I would be sucking. I assume being this was the first time Jill felt my cock her pussy was drenching her panties. I could smell the air permeating with lust of her secreting love juices. I reached behind Jill, undid the bra clasp on her black bra and helped her get it off over her arms. I pulled her tight to my chest feeling those lovely boobs and hard nips pressing into my chest as she went back to stroking my cock. "Jill I have desired to have sex with you since your 16th birthday. You were so hot looking that day. I used to look for your panties and sleep with them on thinking I was in you as I wanked into them. They used to fit so tight. Sometimes I would sneak one in under the pillow case so I could breathe you perfume all night." "Oh Rich if I had only known. I used to come home after a date wishing it were you that had made a deposit in me. I wanted to be so close to you." As Jill was saying that her thumbs hooked into my boxer waistband and was tugging it down. She was lowering herself to the floor as they were going down my legs and she was dragging her pointed tongue down the center of my chest, over the belly button and down to my hard cock. She smiled looking at the seven inches in front of her eyes. It was up and twitching in anticipation of a warm mouth encircling it. It had a drop of precum at the eye. What was she going to do? "Jill I want to eat you so much and have you flood my mouth with your sweetness. Let's 69 and please each other together. I will lie on my back and you can ride my face. God I want to eat your pussy so much, please." Jill stood and gave me a kiss while at the same time sliding her panties down. My heart was beating like an Indian drummer wanting to lay eyes on her pussy, which I have never seen but just dreamt about and imagined. As she stepped out of her panties, I looked down, saw a hairless mound along with very wet panties on the floor. She took my hands and we headed to the bed. Her bubble butt just jiggled like gelatin. I plopped down and she went around the room and turned out most of the lights. I did not mind at all. I wanted her pussy at my mouth and then my cock in her box. I was developing blue balls wanting her so much. As Jill walked back to the bed, my eyes were fixed on her breast in the dim light. They were so firm, perfect and her nipples looked so hard. When she was neared the bed, I tried to take in every little detail of her gorgeous figure. Her pussy lips looked swollen with blood and the tip of the clit was shining with dew as it peaking from the gash. Jill pushed me down onto my back. Placing her legs on the bed, she crawled on the bed and straddled my face. I placed my hands on her warm hips and let her set the pace. She took my cook into a hand, lifted it and I heard, "I hope you share this with me a lot Rich; to make up for lost time. I see you are excited. You have a drop of love juice showing. I hope that's for me." Never in my life, up until that point, did I ever experience the next feeling. It was my cock head in the back of her throat as she closed her mouth around the shaft. How she managed to get my cock so far in without me knowing it just blew me away. I placed my hands on the top of her hips, pulled her to me as I lifted to bury my tongue into her honey hole. I just felt a moan around my cock as she tensed and gushed. How she managed to get her hands to my nuts when she was gushing I still wonder but that made me load up and fire my gun forgetting for those precious minutes that she was my sister. Her juices were so sweet I sucked like a mad man to get them all. I was glowing all over from them with their magical powers. I was so turned on I did not go soft. She extracted her mouth, flipped onto her back and said, "Finish me brother. Give me what you have left." I swung around, lifted her legs and pressed her knees to her breasts, placed the cock at her entrance and went all the way to the bottom on the initial thrust after she had used her hand to place the cock head at the opening of her steaming pussy. I took a few seconds to catch my breath, lifted and went about long and deep thrust, hoping they were 4 or 5 inches in each move. With each thrust, her pussy was gripping my cock tighter and tighter as she was moaning, "ooo...ooo...ooo...ooo..." with each shove down. She had placed her hands around the back of my neck and we were locked with our foreheads pressing into each other. Her pussy had to be feeling every vein in my cock that was blood filled as tight as it was gripping it. As her pussy was gripping my cock harder, she was stiffening and I heard, "Ohhhhhhhhhhhoooooooooooo, Oh god yes, fuck me Rich, aaaahhhhh, oh god, shove it deeper into my pussy Rich, uuuunnngggghhhh, yeah that's it. OHhhoooo fuck, I'm gonna cum all over your cock Rich, AAAAAHHHHH, UUNNNNGGGHHH." Her gripped nearly broke my neck. I fired my hot sticky cum deep into my sister's hot pussy, spraying the whole insides of her vagina from the force of it leaving my balls and up the delivery tube. "Oh god, sis, your pussy is, AAAhhhhh, UUUHHhhhh, Uuuuuhhhmmmm. Oh sis, Oh god sis your pussy is awesome, Ohhoooooo...ooo...ooo." I collapsed on top of her and we were both panting like we had completed 20 k run as the love juices were seeping from her and coating my balls resting on her butt cheeks. I lay there thinking how I wanted my sister all night but also wanted to sample Gladys. I then whispered, "Let's shower and take care of the other two so we can get together and spend the night together and many more." Her pussy gripped my cock with several flexes as if saying, "Yes, yes." We showered with difficulty, me getting her off with a finger, her tits pressed into my chest and French kissing. I resisted her hands because I needed something yet for Gladys. Since it was Jill that was going to meet Rob, she got dressed. I just put on my boxers. We had called Gladys and Rob before showering and they said to call again as Jill departed. I decided to dress and walk with Jill to introduce Rob a little more and to advise her to call me if she needed help; big brother looking out for sister. When I saw Gladys, my cock stirred. Jill kissed me and said, "Save some for me brother." Jill and I kissed. I offered my arm to Gladys to head back to room were the evening started. On the way I took Gladys into my arms, looked her in the eyes and said, "You don't owe the agency anything tonight. I will take care of it. Thanks for chatting with my sister. I owe you more than the agency fee." I heard, "Rich we all know opposites attract. I was picturing you doing me when it was Rob in me. Jill never mentioned she had a brother that is a gigolo." "She didn't know Gladys." "Well if I get horny can you take care of me so I don't have to call the agency since I talked your sister in trying you on for size?" "Just call anytime Gladys. You are so hot. I have been hard ever since leaving Jill with Rob thinking of eating and fucking you." By know we had reached the room and as we stepped inside, she felt for my boner and said, "I have been thinking of this doing me all night," as she took my hand and moved it to between her legs up to her box. Her inner thighs were soaked with love juices and she did not have any panties on. We just went into wild kissing, groping, clothes flying and getting each other naked as fast as we could. We held tight to each other when we had gotten naked to catch our breath. I have been with lots of broads but this one had my fire stoked on high. "Rich, I want you to fuck me doggy and show me how good you are at it, then let's 69 and I want to drink your cum, then if you have enough stamina left I want you to fuck me in the ass before joining your sister for the night. Remember I want more of you in the morning so don't give it all to her. You have the rest of your life for that." We did, as Gladys desired. In the shower then before heading to my sister, Gladys said, "Save that morning hard-on. I want to watch you do your sister doggy while Rob does me. Then you can watch Rob do your sister and if it turns you on, I want you to do me in the ass again. You are awesome at it. I am sure glad I called your agency and it worked out the way it has." "I am happy also Gladys. You are one hot babe." We called Jill and made the switch. I headed to Jill and Rob headed to Gladys. Rob and I spoke in the hall how things were working out great and that the night was not lost. I told Rob I would pay the agency for both Gladys and Jill. He said, "Nope, the night has been so great I will pay the agency like you and what the heck the rest would have been ours anyway and this is better than pay. See you in the morning." Rob had no idea yet of what Gladys had in mind for the morning and I had already bought into it. I was hard thinking of watching Rob doing Jill in a doggy position and watching her reaction. When I got to the room, Jill was all smiles and said, "Now we can pick up were we left off." She walked over to me, opened her robe and said, "Are these nicer than you had pictured when we were young?" I just leaned into one with my mouth open to inhale it and moaned, "Uh-huh." The nipple was already hard as she placed her arms tight around my head to hold me tight to her milk jugs. My right hand lowered itself to her mound and I let the middle finger find the gash to play with the kitty. She moaned went it made contact and pulled me tighter to her boob. After a few minutes I heard, "Rich, lie on your back I want to ride your cock." I was thinking, well being a gigolo I had better do as the customer asks. Jill tossed her legs over me after I had positioned myself in the center of the bed. She was looking me in the eyes as she guided my raging hard-on to her hot cave. As she lowered herself, I heard, "Mmmmmmmmm," as my cock went in further and further, stretching her walls, waking up ever nerve in there. She did not stop until her butt was resting on me and had all of my cock in her. I was cupping her lovely breasts as she was lowering herself but was not massaging them. I wanted her to focus on a cock and her pussy while she was taking me into her. A Gigolo's New Encounter. Jill began small humps and her pussy was gripping my cock. Her walls must have felt my veins engorged with blood. I was thankful I had fired a lot already so I did manage some control but looking at my sister, her boobs, and the pleasure on her face was getting to me; feeling her hot pussy working on my cock. Jill lowered herself to kiss me, bringing her mouth to kiss my face all over, shoving her tongue into my mouth every time she was near it. I began to massage her awesome boobs and soft pinch the hard nipples. Jill was starting to moan as her pleasure built. Slowly I managed to take her left nipple into my mouth, swirling my tongue around it and gently kissing around it, sucking it gently from time to time, as my tongue swirled around the nub. "OooooHHHHHHH," came from Jill's lips as she first felt my lips on her sensitive nipple. I moved her body so I could do the right breast the same way and again received the "OooooHHHHHH, as her pussy was gripping my cock tighter. Here I was working on my sister's boobs as she was feeding herself my cock. The juices were stirring to be fired into her hot pussy. How much longer could I hold back? Jill lifted up, placed her hands on my shoulders and began to increase her speed of humping having closed her eyes. I knew she was setting herself up for a cum. Now she increased the amount she let slip out and back in. "Ooooohhhhhh, aaaahhhh," Jill moaned as she let my cock slide out of her until just the head was left in then lowering herself back down all the way taking my rod, her brother's rod, inside her steaming pussy once again. I decided to play with her breasts and nipples with my fingers to see if I could get her coming cum more intense for her. "Ooooohhhh god, aaaaahhhh, yes Rich yes yessssss!!!" She moaned louder as she continued to increase her tempo of sliding my cock into her pussy deep and hard. Her orgasm hit her. From her lips came, "Ohhhhhhhh, yessssssss, aaaaaaaaahhhhhhh!!! Ohoooooooooooooo, god Rich!!!" Jill's juices were flowing out of her cunt all over my cock and balls. They were so hot. I stiffened and made a deep deposit of my nut juice, showering the insides of her pussy, which caused Jill to have a more intense orgasm, almost making it impossible for me to finish my last few shots as her pussy clamped down hard on my cock. The cocktail was running down the crack of my ass and making a huge wet spot on the bed. Jill collapsed on top of me and her pussy kept milking my dick. I could not believe my sister was this hot. Was it for sex in general or me? God I sure have been missing out. She had my adrenaline going but she had drifted off to sleep. I managed to scoot out from under her. She was face down on the bed. The more I looked at her bubble butt the more my hormones woke up and I was stiffening again. I spread her legs apart gently to get a good view of her. The more I viewed my sister's playpen the harder I got. I slipped two fingers into the inviting pussy, leaking with my cum and her juices. I began to finger fuck her. I then positioned myself on my side so I could slip my other hand under her and play with her clit at the same time. She was moaning but appeared not awake. I decide to spread some of the juices over the wrinkled opening of her other hole. As the fingers slid over it all wet and slippery, Jill would moan a lot and hump a little. I kept playing with her clit. I could tell she was building to a cum. Her tempo of humping my finger was increasing. I felt sis tense to cum. I inserted a finger into her ass hole at the same time as she exploded with her orgasm and was rewarded with a loud, "OOHHHHHHHH God, Yes, Yes, Yes," as she thrashed on the finger on her clit and trying to get more finger into her ass. She went completely limp after the cum. I was hard, very hard. I grabbed a pillow and worked it under her belly to raise her stomach up, well her ass. I spread her legs further and lowered myself so I could tongue fuck her pussy and her asshole if she would allow it. I was pleased on hearing moans of pleasure coming from her lips as my tongue made flesh contact. Her juices were so tasty. My sis was hot, god she was hot. I decided to press my luck further as I guided my cock into her pussy. After a few slow and long thrust, I decided to try the other hole. I pulled out of her pussy and placed the head at the ring. I waited for a reaction and it was just a soft, "Mmmmmmmmm." Did she and her ex do this or other guys? I pressed harder making sure I dribbled a lot of spit at my cock while supporting myself with my hands on the bed so as not to crush sis, and to watch my cock disappear into my sister. I pressed harder at the ring and her ass raised some as if to make it easier. My heart started to beat hard and my cock was getting harder knowing where it could be in a few seconds with out her objecting. I decided a gently shove was in order. The result was, "Oh God yes that feels so good Rich." That startled me. I was in her and she liked it. I just took it easy and with each in movement, I heard, "Mmmmm...mmm...mmm...mmm...mmm...mmm..." When I discovered my balls where hitting the inside of her thighs my tempo picked up. The soft, "Mmmmmmmmm," continued but at a more rapid pace. I reached my point of no return and fired the last few drops of love juice with many blanks following. I growled, "Uggggggghhhhhhhh, Uggggghhh, Ugggghhh, Ugggghhhh," as I made my deposits and heard, "Yes, Yes, Yes, yes," as Jill body stiffened and she herself had an orgasm. When I lowered myself, I made sure I did not come out and rolled Jill onto her side. I fell asleep with my one arm around her, cupping a boob and my cock buried in her ass. The ringing of the phone startled us. I was on my back and out of sis. Sis grabbed the phone and said, "Fifteen." "What was that?" "Gladys wants you and me to come to her room so she can watch me take care of your morning hard on. I told here in fifteen minutes we would be there." We showered and I did not say anything about doing her in the ass since she did not bring it up either. She just kept thanking me for making her feel the best she ever had felt when having sex. We headed to the room where Gladys and Rob were waiting for us. When we entered, Jill and Gladys went to embrace each other and into some serious French kissing with their hands feeling each other's mounds through their clothes. I was shocked but my cock woke up. I could hear them moaning into each other's mouth. Rob and I looked at each other with bugged eyes. I decided to strip and get ready for whatever Gladys asked me to do. Rob in his boxer was making a tent. They seemed to have generated a mini cum in each other because they broke the kiss, placed their chins on each other shoulders, shook and panted while rubbing the mounds. I then heard Gladys say, "Well Rich your sister is hot and wet. I want to watch you fuck her in doggie position." Jill was stripping and I had pre-cum already showing. After Jill had stripped, she walked over to me, grabbed my cock, smiled into my yes, lowered herself and inhaled my cock. I moaned as her warm wet mouth clamped around my cock. She was mouth fucking my cock for a minute or two when she broke the contact, stood, wrapped her arms around my neck, pressed her awesome tits into my chest and kissed me. A hand went to my cock with soft stroking and she then leaned into my ear and whispered, "Do my pussy to get yourself all nice and wet and then fuck my ass like you did last night." My eyes shot open and my heart palpitated. I reached under her to lift her and carry her to the bed. As I placed her on her back, she rolled onto her stomach and then up on her knees to present me with her awesome looking wet bottom. I was afraid I was not going to last long once I got started. I decided to kneel behind sis and tongue fuck her pussy and ass hole until she had a cum. I spread her butt cheeks so I had great access to her holes and buried my face. I then heard, "That's it Rich, eat your sister. God she loves it. Her tits are swaying. She is a real slut letting you do her like that. Hurry up make her cum and then bury that awesome cock of yours into her. Make her beg for it. Oh, Rob your cock in me feels so good. Pinch my nipples harder hon." Hearing Gladys sent my tongue into high gear. I was getting blue balls wanting to do my sister with my cock. Hearing my sister letting out with, "Mmmmmmm...mmmmm...mmmmm," as my tongue was working both holes was not helping me stay cool. I then felt her tense along with a huge air intake and then, "Rich, I'mmmmmmmmmmmmmmmmmmmmm, OHHHoooooooooooooo god, Ohhhhhhooooooooo Rich, god fuck me now, fuck my ass." I broke with the mouth contact, aimed my cock at her pussy, and buried it with one shove holding her hips. I then gave her three pumps, withdrew it, placed it at her tight ring and shoved. I was pulling her back onto my cock with my hands on her hipbones as she screamed, "Oh God your cock, Ohooooo your cock, give me your cock, Ohoooo, Rich I love your cock in my ass. The head had popped in so it was a matter of burying it further. "That's it Rich, do your sister then do me. She is loving it. She is sailing. Fire your family juices into her. Make her long time wishes real. God, Rob I'm ready watching them. Give me your juice. AAAAAAhhhhhhhhh, AAhhhhhhhh, Ahhhhhhhhhh, Ohhhhhhhhh Rob." Because of Gladys's orgasm, it triggered probably Jill's and mine. I stiffened and fired deep into her, 1st blast, 2nd blast, 3rd blast, 4th blast and weaker ones as we both were moaning aloud our pleasure. Sweat was dripping off the end of my nose onto my sister back. She had collapsed from the intensity of her cum and I went down with her as I was firing the last of my juices into her. I was lying on top of her, with my sweaty body, as we panted for air. It seemed like hours in that position but must have been less than 15 minutes when Gladys said, "Shower time you two, I want Rich's cock now." I extracted myself from my sister, rolled onto my back as she lifted to give me a kiss and say, "I love you Rich." We headed for the shower and came out with towels wrapped around us. Gladys used a finger for me to move to her where she was leaning back on the bed on her elbows with her legs hanging over the sides. She looked me in the eyes and said, "Kneel on me and feed my mouth your gorgeous piece of meat." My cock was already perpendicular to my body when I dropped the towel and climbed on the bed to feed her my cock. She inhaled the piece of meat like my sister did. Where did they learn to do this? God it was awesome. I heard Rob let out soft moans so knew sis was working on him. When I was rock hard, Gladys pulled my cock out and said, "Rich, fuck my pussy but do not fire and let's watch Rob do your sister. If it gets to you, shove it in my ass and give me some warning that you will soon do it." I moved so Gladys could get into doggy. I looked at my sis and Rob. She was on her knees and he was feeding his cock into her pussy. Blood rushed to my cock seeing my sister being fucked by a friend. I then inserted my cock into Gladys's wet and hot pussy. I really had to concentrate on viewing the scene and put the senses my cock was getting from her tight pussy out of my mind. Seeing Rob fucking my sister was making me build without humping Gladys. Jill was moaning sounds of pleasure, which was not helping me. I heard Gladys say, "Isn't that a hot scene Rich watching your sister's tits swing as Rob is fucking her deep with his awesome cock. She looks like she is in heaven. Are you hurting Rich? Do my ass love and makes us both feel good as we watch them." I was out of her pussy in a flash, placed my cock at her ring, grabbed her hips and shoved slow and easy until the ring snapped around my cock after the head slipped in. I then did small humps, burying it inch by inch, as I watched my sister tits sway to Rob's thrusting, with him having his eyes closed and holding onto her hipbones so he could be deep in her. Somehow once being inside of Gladys's ass I slowed down my building to a cum and was enjoying the humping of her tight ass. She was moaning sounds of pleasure. I then heard from Gladys, "Rich fire before they do or after. I want to watch them have their pleasure trip." I said, "Gladys I want to hold off if I can and watch also then go a second or two after then have finished." I slowed my humping of her ass and we watched. It amounted to my cock twitching from time to time and me holding it at a certain point with out moving forward. Rob and Jill were both sweating and she was begging for his cock faster and deeper. I watched my sis take a hand and go for her clit. I almost lost my cool but concentrated harder on her. We all heard, "Now Rob, now. We saw her body convulse and her mouth fly open to let out with, "AAAAAhhhhhhhhhhhhhhhhhh, Ohhhhhhhhhhoooooooooooo." Rob stiffened and pulled her back tight as he fired his juice from his gun into the condom he had used, growling out his cum as he was firing. His flexing cock had to make sis's pussy feel good. I grabbed tight onto Gladys's hipbones and went for it. She was hunching back to my forward thrust and in a matter of seconds, we both were moaning our cums as the others were in the final throes of theirs. I was firing the little I had left of my sticky cum deep into her bowels as she was saying, "So good, so good, yes, so good." She slowly let herself down and I went with her. We placed our faces to face each other and managed some soft kisses with both of us smiling our satisfaction of the past few hours. Gladys humped a little to tell me it was time to pull out. I rolled onto my back and she asked me what my plans were for the rest of the day and tonight. I told her I had not made any but would probably not go to work since I fired so many shots the last few hours that I needed to re-coup. She grinned and said, "Can you fix me up with black hunk from your agency since you know me a little for tonight. I have these rooms you know." "Sure Gladys I can arrange that." "Great please do and then you and your sister can have the other room to get better acquainted." Hearing that, my cock started to expand. Gladys noticed and said, "Down big brother." "Thanks Gladys for all you have done for me and sis." "You will take care of me when I call for help will you not Rich?" "Yes Gladys, I will be very happy to help you." I heard Jill say, "Rich that was hot watching you doing Gladys. I guess being my brother made it hotter for me. I was jealous for a little while. I was wishing it were me again." Then Gladys said, "I talked him into you and him using the other room Jill. So you can get all you want from him but save some for me will you sweetie." I saw my sister lay on top of Gladys, then go to kissing and each humping their mounds into each other. When did my sister become BI?