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Jack The Big-Dick Gigolo

"How I became a gigolo after meeting a rich MILF..."

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Famous Story

My name is Jack, and I’m here to tell the story of how I got involved in the business of being a gigolo, male escort, social companion, or whatever you wish to call it.

I was twenty-three years old when it first began. I was a regular guy; I had a regular job working at the airport. I had a girlfriend. Nothing special.

Except in one area, I have a very big dick. Almost nine inches long when I’m fully hard, and two and a half inches wide. Girls seemed to like the width more than the length I found.

I had enjoyed a few girlfriends, after being a somewhat late starter. I hadn’t lost my virginity until I was nineteen.

That was probably due to the fact I wasn’t incredibly handsome or cute. I wasn’t ugly or anything, more just average looking I guess. As I got a little older I grew into my looks somewhat.

Also, I had recently started working out in the gym, and lost a few extra pounds and toned up. I wasn’t a big muscular guy, but slim, athletic looking. I was fairly tall at six-foot-two and had close-cropped hair.

After having two previous girlfriends, and a couple of one-night stands, all with women of my age or younger, I met Sheryl. She was a year older than me, a blonde slim girl. I met her through a mutual friend.

After chasing her for a date for a month, she finally relented and let me take her out. She liked drinking, quite a lot in fact. She got fairly tipsy on our first date and we ended up in bed together.

Sheryl seemed to enjoy my big cock quite a lot. I certainly enjoyed giving it to her. It wasn’t a serious relationship though. Just a bit of fun really.

I would meet up with her once, maybe twice a week. We would go out and usually end up back at her place to fuck.

One weekend Sheryl invited me to a party at her aunt’s house. I had heard about her Aunt Ingrid; Sheryl had told me she was quite wealthy and lived in central London in an amazing townhouse. I had nothing better to do, plus I assumed I would get to fuck Sheryl afterward.

We arrived at her aunt’s house around eight o’clock, a bottle of wine in hand. It was her Aunt Ingrid’s fiftieth birthday party. I knew a couple of Sheryl’s relatives there, but not too many. I guessed there were around sixty or so people at the gathering when we arrived.

It was a very nice house, as Sheryl had told me. Sheryl and I sat in the large lounge area, chatting with some of her aunts’ friends. Other people congregated in the kitchen and hallway.

Sheryl began knocking back the free booze quite quickly. I just hope she didn’t make a scene and embarrass herself. Soon we found ourselves in the kitchen, with Sheryl downing more champagne.

Sheryl introduced me to Allison, her aunt’s best friend. She was a fairly attractive woman, in her early forties I imagined. She had auburn hair in a stylish bob haircut. She was immaculately dressed in a black skirt, with a black jacket, which showed off a tiny glimpse of what I also imagined must be quite a cleavage.

She smiled and chatted with me and Sheryl for a while, mostly small talk. Allison was quite well-spoken, not posh exactly, but certainly well-educated, I figured. Sheryl seemed to already know her a little bit.

Soon Allison’s husband came over and said hello. He was in his early fifties and a fairly burly but short man.

Allison and her husband drifted away leaving me and Sheryl alone for a while. Sheryl then whispered that if I thought her aunt was wealthy, it didn’t compare to Allison and her husband. They owned a large specialized electronics manufacturing company, and she had helped him run it for the last ten years.

Apparently, they had a much larger stunning townhouse in Kensington, a country retreat, plus various holiday homes and villas around the world.

I didn’t think much more about them though as I soon began chatting with Sheryl’s uncle about football. Sheryl got bored of this conversation very quickly and downed another glass of champagne before heading back to the lounge.

I stayed in the kitchen chatting with Sheryl’s uncle for a while. He was telling me all about his plans to renovate an old derelict house he had just bought.

After twenty minutes or so I thought I had better check on Sheryl. I found her in one corner, whispering and giggling with her Aunt Ingrid and Allison. As I approached, Sheryl saw me.

“Shhh,” she said, giggling again. Ingrid looked thoroughly embarrassed, Allison simply smiled at me.

“Are you okay, Sheryl?” I asked.

“We’re fine Jack,” Allison said, smiling again, “We could all do with a refill though.”

“Er, sure ok,” I said, making my way back to the kitchen.

I wasn’t sure what they had been talking about, but I got a sneaking suspicion it had been about me. I also thought that Sheryl had had enough to drink now, but it wasn’t my place to tell her what to do, especially in front of her family.

I went to the wine cooler in the kitchen but it was empty. I started looking in the fridge when Aunt Ingrid arrived, still looking embarrassed.

“Oh Jack, sorry, I think we ran out,” she said sheepishly, desperately trying not to look me in the eye, “I have some more in the basement.”

She turned and opened a door at the back of the kitchen that led down to a cellar.

“I’ll give you a hand,” I said.

“Oh no it’s fine,” she replied, heading down the stairs.

“I don’t mind,” I told her, following her down the steps.

“Uh, okay,” she said.

At the bottom of the stairs, I found a rather dimly lit cellar. There were a couple of wine racks full of bottles, plus two large deep freezer units, and some other assorted junk.

“If you grab some of these, and a couple of those too,” Ingrid said, pointing to various bottles.

“Sure,” I said.

Allison appeared at the top of the stairs.

“Can I help?” she asked coming halfway down. I passed some bottles to her and she took them up to the kitchen.

Ingrid took some bottles upstairs, telling me to grab a few more, which I did. Allison appeared back down in the cellar to help me.

“You like this one?” she asked me pointing out a particular wine.

“I’m not much of a drinker I’m afraid,” I said.

“Not like Sheryl then,” she laughed.

I laughed too, “Yeah she does like a drink, doesn’t she?”

“I’m sorry if we embarrassed you before Jack,” she said.

“No it’s fine, I didn’t know what it was all about really,” I replied.

“Well I’m afraid Sheryl started talking about you my dear,” she explained.

I couldn’t help but notice the door to the kitchen had swung closed, making it even darker down here. But not dark enough for me to not notice one of Allison’s jacket buttons had come undone, letting me see much more of her ample bosom.

“Oh? About me?” I inquired.

“Yes, or rather about a certain part of you,” she grinned.

“Oh. Oh, I see,” I said, thinking that Sheryl had a big mouth when she’d had a few drinks.

“I think it rather embarrassed Ingrid,” she said, moving closer to me.

“I’m sorry, she does get a bit silly when she drinks too much,” I said.

She touched me on the arm. “No, it’s fine Jack, I don’t mind at all, in fact, I was quite intrigued.”

“Intrigued?”

“Come on Jack, you know what I’m talking about,” she said giggling, still holding my arm, “Sheryl says you have an absolutely huge dick.”

“She did?”

“Yes she did,” Allison grinned, a real glint in her eye, “So I sneaked down here to see if it’s true.”

I felt a bit nervous, this had never happened to me before, an older woman showing an interest in me. Still, I liked the attention.

“So what do you say Jack?” she asked, grinning and rubbing my arm, “How about me taking a quick peek?”

Again I looked up at the door to the kitchen, it was still shut. What the hell I thought, it would only be for a second.

“Um, okay,” I said.

She smiled again, as I undid my belt, and unzipped the fly on my jeans, pulling them down to reveal my boxers.

“Let me, darling,” Allison said, pulling the waistband out on my boxers with one hand, and reaching inside with the other. She felt the end of my dick, grinning again. She cupped my balls, and then pulled me out over my shorts.

“Oh my God!” she exclaimed, “You’re huge.”

My dick sat resting against my shorts now, about five inches flaccid, almost two inches across. She ran her fingers up and down my shaft, then gripped it firmly, slowly starting to wank me.

“Jack, it’s so lovely and thick,” she giggled.

I was starting to get hard now.

“Mmm, there we go Jack,” she said smiling, feeling me getting bigger in her hand, “Let’s give him some encouragement shall we?”

Allison undid another button on her jacket, revealing more of her substantial cleavage. She had lovely big tits. She grinned at me and returned to wanking me slowly.

“You like that view do you Jack?” she asked, as I stared at her boobs, looking like they were about to pop out of her jacket.

I nodded.

“Oh Jack, you’re so big,” she purred.

I was now at full erection, almost nine inches long, and two and a half wide. Allison stared at it lovingly.

“Jack, you’re making me all wet,” she whispered, looking into my eyes, “I’ve always wanted a man with a really big cock.”

I smiled at her. “Really?” I said.

“I bet you’ve made a lot of women very, very happy, haven’t you Jack?” she giggled.

I looked back up at the kitchen door again, making sure no one could see us. I could hear them all upstairs singing happy birthday.

“Jack, I’d really love to see you again, you know?” Allison said, now wanking me with both hands.

“I don’t know, I don’t think Sheryl would like that,” I said.

“Well, I don’t think she’d like what we’re doing now either, but it’s our little secret, isn’t it?” she beamed at me.

She was really quite attractive and had killer big, big boobs. I couldn’t say I wasn’t seriously tempted.

“A secret from your husband too?” I asked.

“Of course. So what do you say? I’ll get a nice hotel suite for us next week sometime?” she asked cheekily.

“I don’t know, I just…” I stammered. She was very nice, but I didn’t want to be caught having an affair, especially with the wife of a rich and possibly very powerful man.

“Look, I tell you what Jack, a few years ago I once hired a male escort,” she explained, “He was very handsome, but he didn’t have anything like the equipment you’ve got.”

“Okay…”

“What am saying is, he charged me five hundred pounds an hour. I’m more than happy to pay you the same,” she offered, smiling, and giving me a peck on the cheek.

“You want to pay me to…” I stuttered.

“To fuck me, yes dear. Let’s have a nice two-hour session, shall we? That’s a thousand pounds to fuck a MILF with great tits, Jack. Isn’t that what you young men call a woman like me?” she whispered in my ear.

I smiled, intrigued.

“I’ll be very discreet dear, I promise no one will ever find out,” she said.

I had to start thinking about this seriously now. A thousand quid to fuck this busty older woman? It had always been a fantasy of mine. Plus I could do with the money, what was there to think about?

“All right,” I said, nodding.

“Mmm, good boy,” she said, smiling, giving me a quick kiss on the lips, “I can’t wait to get pounded by this huge cock.”

Allison was very well-spoken, but certainly had a dirty mouth when she wanted. She looked up at the kitchen door.

“We’d better go dear, don’t you think?” she said, carefully stuffing my cock back in my shorts, “So see you next week?”

We quickly exchanged numbers before returning to the party, no one seemed to have missed us. Allison held her husband’s hand and kissed him. He had no idea just a minute earlier his wife’s hand had been wrapped around my thick hard cock.

I stayed a few minutes more, and then collected Sheryl who had almost fallen asleep on the sofa. On our way out Allison gave me a cheeky wave goodbye. I smiled and then turned to hold Sheryl up as we left. She had had much too much to drink.

That meant I probably wasn’t going to get any from her tonight. I drove her home, and she had fallen asleep by the time we arrived. I got Sheryl inside and left her on her sofa.

When I got back to my place I had time to think about Allison and her amazing offer. I was looking forward to seeing her again. I had never thought before that the size of my manhood was a sellable commodity. Still, it was exciting.

The next day I kept checking my phone for messages. She had told me I should wait to hear from her, as she had to be alone when she messaged or called me, or her husband might suspect something.

She kept me waiting; I didn’t hear anything that day, or the next. I started to feel like maybe it was all talk, or she had chickened out. I was disappointed, I thought about sending her a message, but I didn’t want to get her in trouble.

But finally, three days later I got a text from Allison. She asked if I could meet her next Friday around 12.30 pm for a couple of hours.

I was supposed to be working that day, but what the hell, if I couldn’t get the day off I would just call in sick. I was going to be a thousand quid better off anyway.

I replied saying that would be fine, and that I was looking forward to seeing her again. A few minutes later she text me saying she had booked a room at a well-known five-star hotel in Kensington. She also confirmed she would have a thousand pounds in cash ready for me, not that I had asked about that.

I replied to her, saying that was okay and I would see her there.

The rest of the week I thought about my upcoming meeting with Allison. I wondered exactly what she would be expecting from me. Did she want me to do a striptease or something? That would make me feel a bit uncomfortable.

A few days later she sent me a text with a photo of herself. She had taken a selfie, looking down at herself, so I could see down her blouse a little to view her full cleavage. She was blowing me a kiss in the photo. The message also said she was looking forward to sucking my big young cock.

I got a full hard-on seeing that and sent her a photo of my boxers bulging from my erection.

The following Friday I called in sick for work early in the morning. Then I spent the morning getting ready. I showered and shaved, trimmed back the pubic hair above my dick, and shaved my balls.

I had had my hair cut the day before. I had gotten my suit dry cleaned and so dressed myself in it, and put on my most expensive aftershave. I wanted to look my best for Allison.

I made my way up to Knightsbridge on the train. I bought her some flowers on the way.

I arrived at the hotel around noon, a bit early, but I didn’t want to be late. I went and got an orange juice in the coffee shop down the street and waited there.

At 12.30 pm I returned to the hotel lobby. It was obviously very expensive here. All the guests seemed very rich, and well dressed, with expensive cars collecting and dropping them off.

A large Arab family arrived and they had numerous concierge and lobby staff fussing over them.

I was waiting for a text from Allison to let me know what room she was in. I sat in the foyer on a large comfortable sofa. At about 12.45 pm Allison finally rang.

“Hi Jack, are you here yet?” she asked.

“Yes, I’m downstairs in the lobby,” I replied.

“Oh okay, sorry I got here a bit late from the office, I was just getting ready for you,” she apologized.

“No, it’s no problem Allison,” I told her.

“Okay thank you, sweetie, anyway I’m in suite 1601,” she replied.

“All right, I’ll come up then?” I asked, not being sure if she was ready for me.

“Yes darling, see you soon,” she said and hung up.

I made my way to the elevator bank, and up to the sixteenth floor. I walked down the corridor to Allison’s suite. As I approached the door I suddenly got a fit of nerves.

I had never done anything like this before; I wasn’t sure what exactly Allison was expecting from a paid escort, which is what I had become for today at least. Maybe I would be too nervous to perform and make her happy.

Then I thought about the big tits waiting for me on the other side of that door and knocked. A moment later and Allison opened the door.

She smiled at me, somewhat shyly I thought.

“Hi Jack, how are you?” she asked, quickly glancing down the corridor.

“I’m fine,” I said, presenting her with the flowers I had bought, “Are you okay?”

Allison looked just slightly nervous.

“Sorry, I’m okay,” she blushed slightly, “It’s just I haven’t done this in a long time.”

I thought I was the one who was supposed to be nervous here.

“Sorry, please come in Jack,” she said taking the flowers, “Thank you for these, that’s very kind, you didn’t have to do that.”

“My pleasure,” I told her, closing the door behind me.

Allison embraced me, kissing me on the lips. I put my arms around her, kissing her back.

“Mmm, are you all mine now Jack?” she whispered in my ear.

“That’s right, I am,” I whispered back, kissing her neck.

Allison was wearing a nice fairly short black skirt, showing off a bit of thigh, with black stockings and high heels. She had complimented it with a tight white sweater top, which accentuated her large bust, and a nice bit of cleavage on view.

She led me down the hallway of her suite, past the bathroom, and into a nice comfortable lounge area. There was a nice view of rainy London from the floor-to-ceiling window. She invited me to sit on a large sofa.

As I sat she placed the flowers on the table to the left. She opened a bottle of champagne on the table, pouring us both a glass.

I sipped my champagne, as did she, standing in front of me, looking down at me.

“Oh I’m going to enjoy this,” she said, grinning.

“Me too,” I replied.

Allison giggled, sitting next to me.

We chatted for a while, sipping our champagne. I wondered if she wanted me to make the first move, or as she was paying for this session, that she wanted to take charge. After a few minutes of small talk, however, she had not made any moves on me, so I decided I should be the one to do so.

I took her champagne glass from her, placing it on the table to the side. I then took her head gently in my hands and pulled her in for a kiss. I kissed her gently to start with, then with more urgency.

She kissed me back, as I slowly unbuttoned her sweater top, revealing her large bust encased in a black bra. I fondled the top of her tits.

“You’re a naughty boy, aren’t you Jack?” she said kissing my neck, “I’m supposed to be the one undressing you.”

She pulled my jacket off me. I unbuttoned her sweater some more, then pulled it off her. I kissed her again as I reached around and unclasped her bra.

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She pulled off her bra to reveal her huge, huge tits. I had never been with a woman with such large boobs before. I groped and caressed them for ages.

“You like that Jack?” Allison asked.

“Oh yeah,” I told her, “Allison, your tits are amazing.”

She giggled as I sucked and licked on her nipples, “You’re a real boob man aren’t you Jack?”

I nodded, my face buried in between her huge tits.

“I guess you don’t get much big tit-loving with that skinny Sheryl,” she teased.

Sheryl was a 34B. I was guessing Allison must be 38G or 38H, something like that. Damn, I loved these tits. But I was getting carried away, forgetting why I was there. I was supposed to be pleasuring Allison.

But before I could compose myself, Allison gently pushed me back into the sofa.

She then dropped to her knees on the floor, spreading my legs wide, positioning herself between my thighs. She caressed and massaged the huge bulge in my trousers for a while, staring at it lovingly.

Then she unbuckled my belt, pulled off my trousers, and then returned to massaging my cock through my white boxers.

“Oh Jack,” she grinned, “I’m going to really enjoy this.”

Allison yanked on the waistband of my boxers, smirking, pulling them down slowly as my cock popped out for her. She stared at it lustily as she pulled my boxers off.

“God, you’re fucking huge,” she said, never taking her eyes off my cock, “Take your shirt off honey.”

She pulled herself closer, kneeling between my thighs. She began playing with my cock, caressing it lovingly at first, and then she began slowly wanking me.

“Wow, it takes two hands,” she giggled, “You’ve got lovely big balls too Jack. I didn’t notice that before.”

“Thank you,” I replied, taking off my shirt so I was now naked on the sofa.

Allison began massaging my balls, cupping them. She then started kissing them, nibbling at my sack. Soon she was licking her way up my shaft to the head of my cock, grinning from ear to ear.

Then she started lightly beating my cock over her face; giggling as she did so, “I never had such a big dick on my face.”

I smiled as Allison went back to blowing me. She sucked and slurped, slurped and sucked. Slurp, slurp; suck, suck. She clearly loved having a big cock to play with and had a huge grin on her face every time she came up for air.

“You look like you’re worshipping my cock Allison,” I told her, smiling. Damn, she looked good doing it too.

She giggled, “Oh I am. I bow down to your big dick Jack,” she said, slurping some more, “I worship at the altar of Jack’s huge cock!”

She continued sucking me, admirably attempting to get her lips down to the base of my dick. She started to gag about two-thirds down, however.

“Can’t quite get there baby,” she smiled up at me, “Can Sheryl deep-throat you?”

I shook my head, grinning.

“I’m betting she also has no idea you’re not at work today?” Allison asked, smirking.

I shook my head again.

“Mmm. Bad boy,” she grinned blowing me a kiss as she wanked me, “Poor Sheryl, she has no idea her man is naked in front of me and I get to play with his huge dick all afternoon.”

I smiled at her, blowing her a cheeky kiss back. Allison smiled. She kissed and sucked on my ball sack, jerking the head of my dick with her hand.

“What about your husband?” I asked, “Where does he think you are this afternoon?”

“Oh, I left our office and told him I was going to lunch with a friend and then going shopping and I’d be back later,” she replied, her lips moving back up my shaft.

“I see,” I said.

“Which isn’t strictly a lie, is it?” she asked, smirking up at me.

“How’s that?” I asked incredulously.

“Well, I came shopping for a big dick,” she said in between mouthfuls of my cock, “And now I’m eating it.”

She giggled, as did I at her logic.

“I didn’t tell him what I was going shopping for. As long as I go back to the office later, I really haven’t lied, have I?” she said, laughing now.

I laughed too. Allison went back to slowly sucking me again. I reached down to grope her huge tits. They were natural and fantastic.

I noticed she was fiddling with herself through her panties with her other hand. She was obviously getting excited. I pulled her head up, kissing her on the lips.

“Would you like me to return the favor?” I asked.

“Oh honey, I’m sure you’re very good, but I really asked you here for something other than your tongue,” she replied, kissing me back urgently, “I can’t wait any longer Jack, I want your fucking huge dick inside me.”

Allison stood, removing her skirt, and letting me pull down her panties. She kept her stockings and high heels on as she pushed me back into the sofa and moved to sit astride me.

As she did so I felt her pussy for a moment, slipping a finger inside, she was very wet already. I guess sucking on her first big cock had really done it for her.

“Jack did you, er…” Allison began.

“Oh sure,” I said, fumbling quickly for a condom in the pocket of my jacket at my side.

“Let me, honey,” she purred, slowly rolling it on over my dick.

She then kissed me for quite some time, building her anticipation.

“Oh Jack, I’ve been looking forward to this all fucking week,” she whispered.

She then gripped the head of my cock firmly and gently guided it into her pussy, then relaxed her thighs to lower herself onto me.

“Ohhh fuuuck!” she cried, as her wet pussy slid down my length until she had taken me to the hilt, “Fucking huge, fucking huge, big boy.”

She kissed me again, as she slowly began moving up and down on my cock, her eyes closed. I began playing with her tits; they looked so good just inches from my face.

Allison slowly began to build up a rhythm, she was so wet, I could feel her juices running down the side of my balls.

“Jack, you fucking huge big stud,” she gasped, starting to bounce faster now, “Fucking huge dick, fucking big dick stud.”

She was really enjoying herself now. Her hands were around my neck now, her head back, eyes closed, bouncing fast and hard. She was in big dick ecstasy now, she looked so hot.

“Oh Jack, Jack, Jack,” she cried, getting close now.

My hands moved to her hips, pushing down on her downward thrusts to encourage her.

She was moaning very loud now, “Oh yes Jack. Yes, yes, oh fuck yes baby, yes…”

A few thrusts later and she came, crying out far louder than any woman I had been with before.

She collapsed back onto me, my face buried in her boobs. After a moment Allison sat back and kissed me over and over.

“Thank you, Jack, that was amazing,” she panted, “I love it, love the feel of your huge big thick hard dick inside me.”

“Allison, you look so sexy,” I told her.

“Yeah? Do you like my body Jack? I’m not too old for you am I?” she asked.

“Oh no, I love your body,” I told her, sucking her big juicy nipples.

“You’re young enough to be my son. I felt a bit guilty when I opened the door before, you looked so young,” she giggled, “But I don’t feel guilty now Jack, I love the way I feel.”

“How do you feel?” I asked, kissing her.

“So good, so wet,” she giggled, “You make me feel young again. I always wanted to fuck a man with a huge big thick cock, I love it.”

“Well, I’m so glad to make you happy Allison,” I said.

She giggled, kissing me, and caressing my chest.

“Now, how about I take you to bed and fuck you nice and hard,” I grinned, putting my arms around her waist and standing up, my dick still inside her.

“Oh Jack, yes please,” she murmured in my ear as I carried her out of the lounge and toward the bedroom, “Fuck me, Jack, fuck me with your gorgeous, beautiful, big young hard cock.”

I pushed open the bedroom door; it was a lovely plush room with a very big bed. There was another large floor-to-ceiling window with another view across rainy London.

I began to move to the window to close the curtains.

“Forget it, no one can see us up here anyway Jack, just fuck me now,” she told me.

I lowered Allison onto the bed beneath me.

“Good boy, very good. That cock of yours never left my pussy,” she giggled.

I was on top of Allison now and began thrusting in and out of her. She was still lovely and wet. Her pussy was fairly tight too. I had thought being older that maybe she wouldn’t be, but I had never been with an older lady before.

Perhaps she had not had any kids; I hadn’t asked her about that so far. Sheryl’s pussy was pretty tight, but she was much younger, and besides Sheryl had told me any woman would feel tight to me because my cock was so thick.

“Oh god Jack, yes, yes,” she panted, as I thrust harder and harder into Allison, “Fucking huge big dick, fuck me, fuck me. Oh, fuck me, you fucking big dick stud.”

Allison certainly liked talking dirty, and I definitely loved hearing it. She was making me feel like a king, my dick was so fucking hard.

I moved Allison’s legs so they rested on my shoulders, her high heels touching my ears. I fucked her deep and hard.

She grinned from ear to ear. “Oh fuck Jack,” she cried, “Oh yes, don’t stop Jack, don’t stop. Don’t you fucking stop Jack, oh fuck meee…”

She cried out, coming for the second time. I pulled out and laid by her side, she turned on her side too, her back to me, my dick pushing up against her ass.

“Oh Jack, you’re so wonderful,” she panted, “You’re such a real man. I’ve never been fucked so good and hard darling.”

That made me feel good, and super hard. I manhandled Allison onto all fours and got myself behind her ass.

“Oh Jack, you’re so fucking horny,” she said, looking back over her shoulder at me, “You’ve got such great stamina, not like my husband.”

“Is that right?” I asked, as I slowly pushed my cock into her sopping wet pussy, “You like fucking your husband?”

She smiled up at me as I began thrusting into her, fucking her doggy style, gripping her hips.

“I don’t know how I’m going to go back to fucking him Jack,” she said, turning to face forward to look out over the view of London through the window, “This is fucking incredible.”

I held Allison’s hips hard, pulling her back into me as I thrust into her wet pussy. She began moaning again, she was loving this. I was glad I was making her so happy.

I could see us reflected in the glass of the window, her tits swaying back and forth beneath her in time to my thrusts, her nipples almost reaching the crisp white sheets.

“Are you going to think about me when you’re fucking your husband next?” I asked her.

“Oh yes, yes Jack,” she moaned.

“Promise?” I asked.

“Yes I promise,” she gasped, “I’ll think about your lovely young thick dick when he’s fucking me, Jack.”

“Cos that’s the only way you’re gonna be able to get off, isn’t it?” I said. I had started to talk dirty with Allison now like I sometimes did to Sheryl.

“Oh god yes Jack, yes. I fucking love that huge cock of yours,” she panted, “I fucking need it.”

I got the feeling I could say just about anything my filthy mind could come up with right now and she wouldn’t mind a bit.

“You’ll never be satisfied with another man after this, will you Allison?” I asked her, banging away harder into her pussy.

“Oh no Jack, only you Jack. Only you and that huge fucking cock,” she cried.

“I think you’re going to become a big cock slut now, aren’t you Allison?” I teased her, spanking her ass as I fucked her.

“Oh yes Jack, I’m a fucking big dick whore,” she purred, “I’m a fucking cheating whore and I love it. Oh god, yes, yes Jack I love it.”

Wow, she was really getting into it. This usually very well-spoken, wealthy, and sophisticated lady was now on all fours and calling herself a whore for her own pleasure. Amazing what a young guy with a big cock could do to a woman.

All this dirty talk was starting to get to me, and I could feel the spunk building in my balls. I thought I had better tell Allison in case she wanted to see me ejaculate; after all, she was paying me for all this.

“Oh Allison, I’m gonna come,” I panted.

“Oh god, not yet darling, not yet my darling Jack,” she said, looking over her shoulder at me concerned, “I need one more Jack.”

“But I…” I started to tell her, but she turned and sat up, kissing me.

“It’s ok Jack, we’ll stop for a minute then,” she purred, “But I really need one more Jack, I want to come one more time. I love it so much.”

“I don’t know if I can,” I told her, kissing her back. My dick was calming down a little, but I wasn’t sure if I was going to be able to last long enough to get her off again. I sat back down on the bed.

“Well Jack darling let’s see,” she whispered in my ear, throwing her arms around my neck, “What can I do to motivate you? Oh, I know.”

“What?” I asked.

“Well, I’m giving you five hundred pounds an hour for a two-hour appointment, so that’s a thousand pounds,” she explained, “But let’s have a bonus system for every time you make me come.”

“Really?” I asked.

“Yes, Jack. I’ll give you another two hundred and fifty pounds for every orgasm. So you made me come twice already, that’s another five hundred,” she said, still whispering.

“Uh-huh,” I murmured.

“You make me come again darling and you’re walking out of here with seventeen hundred and fifty pounds,” she purred, “How’s that sound?”

“Well, okay I guess,” I said, “But it’s not really about the money, you know, I really do love being with you.”

“Oh I know you do Jack, I can see it in your eyes,” she whispered, “And I can feel it in your cock.”

She giggled in my ear, then pushed me back on the bed, and moved to sit astride me.

“Come on baby, one more time,” she said, lowering her pussy onto my cock, “Oh good boy.”

She began slowly riding me, bouncing up and down, my hands all over her tits.

“Sexy girl,” I told her.

She smiled; putting her hands on my chest for leverage, and began to ride me harder and faster. I enjoyed watching her tits bounce up and down.

“Oh yes darling, I love fucking you Jack,” she panted, moaning and whimpering as she rode my hard cock.

I was glad she was on top; I found it easier to not get too excited in this position.

“Fucking big, big dick,” she moaned, “Lovely fucking thick big cock.”

She was in big cock heaven again; her head tilted back, her eyes closed. I held her hips. I encouraged her to fuck me harder by pulling down on her hips on her downward thrust. Then I began thrusting back up into her too.

“Oh god yes Jack, don’t stop. Don’t fucking stop,” she moaned loudly, “You fucking stud. Fucking big dick stud. Oh god, I love it.”

She was close now, she must be. She couldn’t possibly bounce any harder or faster on my dick. Her tits were a wonderful bouncing blur in front of me.

“You fucking sexy, sexy girl,” I told her.

“Oh Jack, fuck,” she gasped, and a moment later came very, very loudly indeed, collapsing on top of me.

She lay there on top of me for a minute or so, her body shaking as I held her.

“Oh thank you, Jack, I really needed that,” she whispered, “I’ve never been fucked so good.”

“You’re welcome,” I told her, “You’re one sexy lady Allison.”

She smiled, kissed me, and sat up. “Okay, your turn Jack,” she grinned, “Come here my darling.”

She pulled off the condom, rubbed some wetness from her pussy between her tits, and lay back on the bed. She pushed her tits together. I understood immediately, and clambered on top of her, pushing my dick in between her huge boobs.

“You’ll never be able to fuck that skinny Sheryl like this, will you?” she teased.

I smiled at her as I thrust in between her tits, Allison holding them together with her hands.

“I bet your husband’s cock won’t even touch the sides now. I’ve ruined that pussy for him,” I teased back. She giggled.

“Fuck my slutty big tits, Jack,” she ordered, “Come all over your cheating little whore.”

She had started with the dirty talk again, and it was beginning to have an effect. I could feel my spunk building again. She grabbed my cock and took it in her mouth, sucking and slurping, running her tongue around the head.

“Oh, I’m a whore Jack. A slutty, slutty whore,” she whispered in between mouthfuls of huge throbbing dick, “Come all over me Jack, call me a whore and spunk all over me.”

I couldn’t take much more of this, I was almost there. I held her head in place and began thrusting in and out, fucking her mouth.

“Oh you fucking sexy little slut,” I told her, “You busty, slutty cheating whore.”

Here it comes, I thought, and pulled out of her mouth, jerking my cock a few times over Allison’s tits.

“Oh yes Jack, spunk all over me” she sighed.

With that, I shot my load, a monster eruption all over Allison’s tits, neck and face. Spurt after spurt of creamy white jism.

“Oh lovely,” she said, “Good, good boy.”

I collapsed back on the bed. Damn, that was a great fuck. Allison giggled, then got up and went to the bathroom to clean up.

After a few minutes of recovery, I went to the bathroom too where I showered with Allison. We both enjoyed washing each other all over.

We kissed for a nice long time.

Whilst we were drying off, Allison’s phone rang in the other room. She went to answer it, and I could hear her talking for a while. I took my time drying off.

She then returned to the bathroom, all dressed, with her make-up re-applied.

“Sweetie, I’m going to have to go back to the office straight away, I’m sorry,” she apologized.

“Oh okay, no problem,” I replied. But really I was a little disappointed. I had started getting a semi-erection and had hoped I would get to fuck Allison one more time.

Allison noticed my semi-erection and smiled. “Oh honey, you young guys have so much stamina don’t you?” she giggled, gripping my cock, “I’d love to stay and suck and fuck you again but there’s some mini-crisis at the office so I have to get back there.”

“Okay, I understand,” I told her.

“I left something for you on the table. When you’re ready to go just drop the key back at reception, the room is already paid for,” she explained.

“Sure, no problem,” I said, putting my arms around Allison, and kissed her.

“Oh, careful my lipstick,” she joked, “Oh Jack, I really want to see you again honey. I had the best time.”

“Me too,” I replied.

“I’m sorry to rush off honey. I’d really love to stay and give you a nice blowjob and drain those balls again, but I really must go,” she explained.

“It’s okay,” I assured her.

“All right, well I’ll call you soon to set something up for next week, okay?” she asked, “I’m so sorry to run off on you, I’ll make it up to you next week, I promise.”

“Sure,” I said.

“Okay, you take care Jack, see you soon,” she said, finally letting go of my dick, pecking me on the cheek, and then she was off and out of the suite.

I heard the suite door close behind her. I went back into the lounge to find my clothes and get dressed. On the table was an envelope, with Allison’s lipstick kiss on it.

Inside I found the thousand pounds we had agreed, plus the additional seven hundred and fifty pounds she had promised me as my ‘orgasm bonus’.

I left the hotel shortly after, and walking down the street in the rain my thoughts ran back over the last few hours, and the wonderful time I had enjoyed with Allison. I hoped I would see her again next week as she promised.

My life was about to change, and little did I know the plans that Allison would have for me…

TO BE CONTINUED.

Published 
Written by Reddead2010
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