A Gigolo's New Encounter.bydark_knight33©
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.