A Gigolos New Encounter

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.