The Making Of A Gigolo 4 Prudence HarrisChapter 2
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Bobby was right to expect both his sisters to visit him that night. Both Mary and Bev came in together, and Mary was almost frantic to climb on him and rub. Halfway to her orgasm, she told him why.
“Fred asked me to marry him!” she panted.
Bobby was afraid Bev would wake everyone in the house with her squeal of delight. She clapped both hands over her mouth, as she realized how loud she was being.
“Is that a good thing?” asked Bobby. He’d never thought of getting married. He liked being able to be involved with several women.
“I don’t know,” she moaned, rubbing faster.
“What did you tell him?” asked Bev, calmer now.
“I told him I had to think about it,” gasped Mary.
“Mary!” squealed Bev again. “Why did you say that? You know you love him.”
“I know,” she panted. “Shut up. I’m almost there.”
She was, and within ten seconds she whined and rubbed furiously, as Bobby sucked at her nipples and stroked her hips. She lay down on him, limp, when she was done.
“My turn!” said Bev. “If you love him, why didn’t you just say yes?”
“It’s scary,” moaned Mary. “I’d have to leave here ... leave all of you ... and go live in a strange house.”
“You could do this whenever you felt like it,” said Bobby, sliding his hands all over her back and butt.
“That’s another thing,” she sighed. “I’m scared of having sex. I just know it’s going to hurt.”
“What we do doesn’t hurt,” said Bobby.
“I know that!” she said, pushing herself up and climbing off of him.
Both Mary and Bobby were astonished to find that Bev had taken off her nightgown. She’d never done that before. Bobby stared at her breasts, smaller versions of Mary’s with the same pink nipples.
“Do you want to be on top of me too?” asked Bobby, staring at her.
“No,” she whispered. “I don’t think I’m ready for that. But your hands feel so good on my skin ... I just want to be next to you ... like this.”
Bobby rolled to his side, and she joined him, snuggling up against him, his wet prick rubbing her belly.
“That feels so strange,” she said. She kissed him, and within seconds she was lying on her back, as Bobby rolled them, to lay half on top of her. His hand was between her legs, and she had spread them for him. She moaned as he slid a finger into her, and kissed him harder.
“That doesn’t hurt?” asked Mary, whispering.
Bev twisted her face away from Bobby’s, to look at her sister, around his head.
“No!” she gasped. “Now it’s your turn to shut up.”
Mary watched, as her brother’s finger disappeared up inside of her sister. Bev obviously loved that. Her thrusting hips made that clear. But Mary remembered the pain, when Bobby had put only a little of his finger in her. Her own hand went between her legs. She’d never put anything inside her, but now, she slipped one fingertip in. She hit her barrier immediately, and felt the twinge of pain as she experimented, pushing against it. She felt part of her fingertip slip to one side of that barrier. There wasn’t room to push much, and when she did, it was uncomfortable ... like picking at a scab. She removed the digit and, while watching Bobby finger fuck her sister, rubbed her nubbin until she clenched her teeth, cumming again, in time with Bev, who broke away from Bobby’s lips to open her mouth wide, and close her eyes tightly as she had an orgasm too.
Mary rolled Bobby to his back. His prick was wet from her pussy, but she didn’t care. She was too inflamed to resist closing her mouth over his prick.
“Ahhhhhhh,” moaned Bobby, as she sucked at his manhood.
She sucked a long time, but he didn’t spurt. When she stopped, to ask him why, he said he didn’t know. It felt wonderful, but he didn’t feel the urge to spurt.
“Jack on it,” he suggested.
She did, sliding her mouth up and down, in time with her hand. Her lips pushed his foreskin back each time.
“Oh yeah,” he moaned. “That’s what it needs.”
Within two minutes, Mary had a mouthful of her brother’s delightful, warm spunk, and swallowed it happily.
Bobby was at the grocery store when he saw Prudence next. She was wearing another new outfit, tan slacks, with an orange and yellow blouse that made her look like she was on fire. She was peering at the label of a can, and hadn’t seen him yet.
“Hi,” he said, pushing his cart almost past her.
She looked up from the can, and her eyes widened. Then, slowly, her pale face began to be tinted with a stain of pink.
“Hello,” she said, having to clear her voice to get the word out.
Bobby looked around. They were alone in the aisle.
“I’d like to see you again,” he said.
She looked around too.
“See me?” she asked. “Is that all you want to do?”
“Of course not,” said Bobby, smiling.
“How do you do that?” sighed Prudence.
“Do what?” he asked.
“Make me feel like this,” she said. “I’m a grown woman, but whenever I look at you, I feel seventeen.”
“You didn’t feel seventeen the other day,” said Bobby, smiling wider. “Not by a long shot.”
She looked around again, nervously.
“I can’t see you again,” she whispered. “I’d feel like doing things we shouldn’t do.”
“Why do you think I want to see you again?” asked Bobby, his smile small now.
“How can you want that with a woman twice your age?” she moaned.
“You’re beautiful,” said Bobby. “I like you. I told you all this already.”
“I didn’t know you wanted to do that!“ she whined.
“A woman like you shouldn’t be made to go without an important part of her life. You’ve deprived yourself. Didn’t you feel good last time?”
“Too good!” she gasped, flushing harder.
“I can make you feel even better,” he said. “I want to make you feel even better.”
“I don’t believe I’m standing here, talking to you about this, in the middle of the grocery store!” sighed Prudence.
“Then let’s talk about it Saturday morning ... at your house ... in your bedroom.” Bobby said it plainly, as it were merely simple conversation.
“Constance...” moaned Prudence, trying to fight the desire inside her.
“Send her to my house. She and my sister are friends now.”
She was about to say “No!“ when he reached out and touched her hand, where it lay, gripping the handle of her cart. That single touch shattered her resistance.
“All right!” she gasped. Then, in almost panic, she pushed her cart, almost running down the aisle away from him.
He played with her, going the opposite direction, and then looking to see which aisle she was going down next. He made sure he met her again, walking past her. If there were other people in the aisle, he said nothing. Once, when there was only one other customer, who was far away, he mouthed the words, “See you Saturday” and grinned, as she blushed and hurried past him. Another time, he reached out and stroked her hand, as he went by.
The fourth time he passed her, she whispered “You’re terrible!“
But, as she hurried off, she was smiling.
He didn’t make it to her house until after ten, Saturday morning. He was still doing chores when Constance showed up at the farm, riding her bicycle, and went into the house as if she lived there.
Bev had found out that she really liked the quiet girl, who wasn’t nearly as quiet once she accepted the fact that she had a real friend. The other girls liked her too, which only added to the strange, almost mystical sense of sisterhood she began to feel with them. Never having been around many kids her age, except in school, she was amazed at the noise and apparent confusion of a house that seven girls lived in. That the boy she had a crush on lived there too was just icing on the cake.
Medanwhile, when Bobby knocked on the door at Constance’s house, it opened almost immediately. A panic stricken Prudence stood there, already breathing hard, as if she’d run to get the door.
“I thought you’d never come!” she blurted.
“I thought you were nervous about me coming at all,” he said, smiling.
“I’m terrified!” she moaned.
“You don’t have to be,” he said. “Can I come in?”
She jerked, and stepped back. She was wearing shorts, and a shirt that buttoned up the front. She was also barefoot. She stood, tensely, frowning.
“Look,” he said soothingly. “I don’t want to make you nervous, or upset, or do anything that you don’t want to do.”
“I have no idea what I want to do,” she said, honestly. “The thought of you being here ... of us ... I just can’t imagine it!”
In fact, Prudence had been in turmoil ever since seeing him at the store. She was inundated with the pure joy of being desirable, as any woman might be, but it had been so long since she had felt that, that it felt foreign. And, like many women, she couldn’t convince herself that a man - especially a handsome, young, muscled Adonis - would find her attractive. She saw all the flaws, when she looked in the mirror. She saw the pooch, where there was extra flesh on her abdomen. She saw the stretch marks on that skin, from when she was pregnant. She saw her breasts, hanging low, heavily, when they weren’t controlled by a bra. She saw the moles, and the pale skin, and the padding on her hips. She believed herself to be fat, though she carried only the normal extra flesh that nature gives a mature woman. At the same time, she had felt Bobby’s passion, as he kissed her, and slid his hand where no man’s hand had been in more than ten years. She’d felt his arousal, pressing against her side as he gave her that wonderful, terrifying orgasm on the couch. Then there were the cultural taboos involved, though they actually took a back seat to her personal qualms and desires. She was at war with herself, knowing that she shouldn’t want more, but wanting more desperately.
And he had plainly offered her more, and was there, in the flesh, because she had said, “Yes.”
“Maybe I should check that window pane,” he said softly.
She jerked, as her mind centered on him.
“It’s fine!” she said, automatically. He smiled, and she felt silly. He was giving her a little push ... but only a little one. “Oh!” she said. “I suppose that would be all right.”
Then, when they got to the bedroom, and he ignored the window, to stand in front of her and reach for the buttons of her shirt, she didn’t know what to do. So she just stood there, as he unbuttoned it, and slid it off her shoulders.
She stood there as he undid the snap of her shorts, and pushed them over her hips, where they were tight. She bit her lip, knowing that now he could see the pooch of her abdomen, with its stretch marks. He turned her, as if she was a department store mannequin, and she felt his fingers at the catch of her bra. It went slack, and he pushed it off her shoulders. His fingers traced over her now-bare shoulders, and she dropped her head, both in shame at being almost naked with him, and because his fingers felt so good, stroking her skin.
The bra dropped to the floor, falling off her limp arms, and she felt a warm kiss on her neck before his fingers went to the bun, on the back of her head.
“Bobby,” she whispered. No one had ever seen her hair down since Harry had died.
“Shhhh,” he said, loosening the pins, and pulling at the long hank of hair.
It fell to her shoulders, and she pulled it forward, to cover her breasts. She almost cried out as he knelt behind her and pulled her panties down, but bit her lip to keep from doing that. A strangled moan slipped past her teeth.
“It’s all right,” he whispered, sliding his hands up the outside of her thighs, to rest on her hips.
She expected him to turn her around ... to stare at her ... to ogle her, with lust-filled eyes. Instead, he simply ran his fingertips over her back, and sides, and arms, until some of the tenseness loosened.
She had no idea how he did it, but when he stepped up to press the front of his body against her naked back, he was naked too. She felt his erection press into her buttocks, and sighed with the ecstasy of knowing he was aroused for her. His hands slid to her belly, and he gripped the extra flesh there.
“I’m fat,” she moaned.
“I love the feel of your skin,” he whispered, his chin on her shoulder.
His hands slid upwards, under her hair, to cup her naked breasts.
“I love the feel of these too,” he said, squeezing them, and lifting them. His fingers found her fat nipples and squeezed gently. She moaned, and leaned back against him.
“I want to make love to you,” he whispered.
Her involuntary step toward the bed might have been disaster, had he not been holding her breasts. Her left foot caught in the panties and shorts that were puddled around her feet, and she would have fallen, but his hands saved her, and let her step out of the obstruction.
That first time was all a blur to Prudence ... a cacophony of an odd mixture of silence, and noises that she knew she was making, but wasn’t making intentionally. She wasn’t sure how she got on the bed, on her back, and couldn’t remember him climbing on top of her. She didn’t even know she’d spread her legs for him, until she felt the pressure of his entry. Quite suddenly, from that point on, she seemed to be at once there, on the bed with him, and floating up above that bed, watching as his hips rose and fell between her knees, and both of her selves were transported to a place she’d loved in the past, but forgotten about completely.
She had no idea how many orgasms she had. They washed over her like waves in the ocean, coming again and again as she let them lift her, and drop her. What she did remember was the ecstasy of being full of hard prick that moved and stroked and massaged her frantic pussy. She also remembered, with crystal clarity, that she had been a fool to go without this for so long. She would never forget one other thing. That was his long, drawn out sigh, when he said “Oh Prudence,” and she felt his hot sperm jetting into her. That brought her back into her body, and she luxuriated in the feeling that he had put a ball of fire into her belly, that was slowly expanding, and would completely consume her.
Amy was waiting for her at the appointed spot. Beneath the coat Prudence could see the younger woman was wearing black nylons and black shoes with heels far too tall for anyone’s comfort. The two females hugged. “So do we take a bus, or should we call a taxi?” Prudence asked.“No point,” Amy said. “It’s not far at all. This way.”She set off down the street, Prudence falling into step beside her. How could the girl walk so fast in those shoes?“So how are you feeling?” Amy asked.“Nervous,”...
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I was doing my 2 years MMS course from Mumbai university and opted for self study hoping that I will get a good job so that I can help my family, as I belong to a middle class family. I tried searching for jobs and hunting various companies for 3 months, but failed to get one as I was studying none of the companies showed interest. One fine day I was returning from an interview from Nerul to Dadar(Two stations in Mumbai). I was as usual rejected, so I was bit sad. I decided to take a local...
Helo everyone this is sameer from Mumbai suburb(mira bhayander) I’m writing my first ever experience of being a gigolo. So please forgive me for any spelling mistake. Please send me your feedbacks on I’m 18 years old and this story is when I was 16. I think I’m the youngest gigolo from Mumbai. I’m 6.2 feet tall with a muscular body and six pack tool size 6 inches but very thick that any women will love to take… So coming to the story 2 years ago I passed my 10 th std and was admitted to a...
Hi there ISS readers. I am back after a long time. This time I am gonna share my new gigolo encounter with a hot matured lady. Thanks to Indian Sex Stories for posting my stories over here. Now coming to the introduction. My name is akhil. I am a gigolo. Meri current location Chandigarh hai. Meri age 23 hai or meri height 5″9 hai or mera lund 7″ ka hai. Mujhe bade boobs or bade gaand wali ladkiya zyada pasand hai. If any lady or girl or bhabhi or any female wants my gigolo service then you...
Hello to all indiansexstories2.net readers. Girls/ Ladies/ Housewifes/ Widow/ Single Ladies, I am Bapi back again to share one more incident of a real story of a fabulous encounter of my gigolo profession. I would like to introduce myself to readers who dont know me. As informed earlier my name is Bapi,age 32, unmarried, located in Rourkela, Odisha. I am working in a private firm and serving as part time gigolo (male escort) for unsatisfied females. If you are lonely or unsatisfied with your...
Dear friends, this is Shiva again from Tamil Nadu. Thanks for all those who spent their precious time, sending feedbacks for my stories Lucky Journey With Lusty Lakshana and Pumping Plumy Padma. All your feedbacks and my experiences after publishing those stories, made me to write this story. Feel free to contact me via my email ids and to have a very safe, secret and enjoyable relationship. My KIK Id is : dazzlingshiva I always feel every girl/lady as a flower and they have to be treated...
Hi readers, my name is Joe from ,am doing my b.com in a reputed college.Am basically from Kerala but live in Bangalore in pg.This is my first story in this site and forgive me if there is any mistake.I thank ISS for providing a site like this to share our story. This is actually how I became a gigolo for school teachers in Bangalore.The story will be in 2 parts & this part will tell you how a horny divorced teacher seduced me and made me a gigolo for her female friends in school. Please forgive...
Hello again everybody my name is Dev and I will be sharing my first gigolo service in Mumbai. I stay at a good locality in Mumbai having rich families around me. I completed my engineering degree so right now I am just having sex with horny ladies mail me at Coming to the story; during my engineering I thought that I should be a gigolo because people complimented me for good looks, height and body. As I know where gigolo start their business from so I went there. I noticed that three gigolo...
Hi dosto app asbhi ko mera mera Namaskar, mera nam Rohit he or me Rajasthan ki city ka rahne wala ho meri umar 34 sal he meri ye pahli kahani he assa karta hu ki app sabhi ko pasand ayegi me iss ka regular pathak hu or chahta hu ki me apni gigolo banne ki kahani app sabhi ke sath bantu dosto bat tab ki he jam me 31 sall ka tha mera ek dost jo kimeri hi umar ka tha us ko kucch sarir pe dad or khaj ki problem ho gai to Hum dono ek Dr ko dikhane chale gae joki ek bahut hi Mashur Dr thi Dr. Mamta...
Hello friends myself Raaz. I live in Delhi. I am sending my first story for you. It is a true story of my life. 2 years ago I came to Delhi for my engineering studies. As I belong to a small town so I didn’t know about the life style of a Metro City. Well now I am coming to my point. I have an athletic body as well as handsome. That is why I am demanded in girls. I lived in Dwarka at Delhi. In evening, sometime I got bored, as I was living alone at my room, so I used to go outside to make my...
First TimeHello, living in Jaipur, a dire financial situation three years ago forced me to look for ways to make money. A friend of mine, a seasoned gigolo (male sex worker), talked this 18-year old into joining his line of work and live a life of luxury. I’m paid big money for providing (and receiving) carnal pleasure. Money was what made me say “Yes” to my friend’s invitation to join the business. I get anywhere between ₹6,000 and ₹25,000 for one night, depending on who I spend the night with. The...
‘I’ll take care of your coat for you, Prudence,’ I offered as I helped her remove her fur jacket. ‘Thanks, Mike,’ she smiled. ‘I’ll see you at the bar after you’ve finished that little chore.’ That was when I noticed Steve Watkins and Barry Reynolds standing between me and the coat room. I could barely conceal my distaste as I attempted to walk around them to hang Prudence’s fur. ‘Did I hear you call your wife ‘Prudence’, Mikey?’ laughed Steve. ‘That’s a name you don’t hear very often. In...
Sissy Prudence (Part 3) (by Sissy Caroline) Section 1 "That's our Sissy Prudence in the garden. Isn't he a delight?" Bridget looked out the window and, despite the fact that boys were not really her interest, she found the sight presented to her was quite exciting. She had never thought that a boy in a dress could be such an erotic fantasy. Prue was working in the garden, which was something he now really enjoyed as a break from his duties inside the house. Not that he was...
Sissy Prudence (Part 4) (by Sissy Caroline) Section 1 "Control, discipline and dependence are all very closely linked Jennifer. Ultimately we want him to be totally dependent on us and we use discipline and other means of control to help us achieve that state of dependence. Although you should be very pleased with progress, he is a long way yet from where he could be as we have discussed previously." "I know that you're right Janice. I love the way he has responded so far but...
Renee bent over and pulled down the covers, which she hadn’t even gotten under, because it was warm in the room. It was still warm but, despite the boldness of her behavior, there was still a residual level of nervousness in her that demanded she do something routine and normal. Turning down the covers served that purpose. “It really is a cute butt,” said Bobby, from behind her. She looked over her shoulder, to see him staring, where the shirt had ridden up to show her bare buttocks. Once...
This was Renee’s first celebration of the 4th of July in Granger. She was a little shy, at first, but then began seeing people she knew. Children ran up to her for hugs, and their mothers and fathers smiled and waved at her. Mirriam also waved, from a line of tables set up on the grass. Lots of women Renee knew were at that line of tables too, and her nervousness disappeared as she walked over and was welcomed. She looked around for Bobby, but didn’t see him. She felt embarrassed, for some...
On a day late in August, Bobby knocked on Liz and Jeff’s front door. He had a bottle of wine with him, and was dressed semi-casually. That was primarily because he had no idea what was going to happen that night. He was there in response to a somewhat formal invitation to attend the celebration of their wedding anniversary. Dinner would be served. Jeff answered the door and smiled, sticking out his hand. “Congratulations,” said Bobby, smiling back. “Thanks,” said Jeff. “Come on in. She’s...
The next morning Amanda had to drag herself from bed. She hadn’t slept well. She hurried to get her father taken care of. He’d had insurance that covered loss of work from a thing like this, so, financially, they were fine. The insurance also covered hiring a person to check in on him, occasionally, during the day, so she knew that his other needs would be taken care of while she concentrated on making the situation at the station improve. She had no idea how to do that, though, and that was...
Hi … This Suresh from Tiruppur,Tamil Nadu…I am the big fan of ISS … I have been regular reader of ISS for the past 4 years… I am the private gigolo and a sperm donor looking for more customer who are in need for pleasure.. Can contact me any time Coming to the story… I have a intentions in sex for past 6 years and I have further checked in google and I came to about a gigolo…. I too started surfing and fount and that person demanding 5,000 for and after that only I came to know its a fraud...
This time of year, darkness came early, but not early enough for me to get some warm up business before Vera turned up in her limo and took me to the hotel. I’d decided to dress in a £3,500 suit I’d bought earlier in the day, but this was nothing to what she met me in the restaurant with. She wore a slinky red dress with matching and rather skimpy lingerie. 104, looking about late sixties, and absolutely stunning. Despite this, people looked at me strangely for being 22 dating someone 82...
You won’t notice me stand out in the Metro crowdI won’t be the one to turn heads at the office party. I don’t make you feel threatened by speaking to your wife or your girl hell and till a few months back I dint even know how to speak to a girl. But this story is not just mine it also belongs to Deepika!The perfect wife a loving mom a generous wife and the ideal woman and fair beautiful a former model who had with age put on weight only in the right places and a face oh what a face it drips...
Hi, my name is anil and I am from Bangalore. I am an average looking guy with a medium built body having a decent 7-inch thick black tool. I am 25 years old. I work as a supervisor in a private company and in part-time I work as a gigolo satisfying women of all age groups in Bangalore and providing services as they wish for the last 3 months. I stay in Banashankari 3rd stage and provide the services all over Bangalore city. Today I am about to share my very first experience of how I became a...
Hi, Indian Sex Stories readers, this is my real sex story. I’m Karan from Delhi. I’m new here, I’m 23, athletic, 6 feet tall and a good looking guy. Right now, I work in an MNC and work as a part time gigolo. My dick is 6 inches big and very thick and got great stamina. This is my first experience of how I tried and became a gigolo, many more stories will follow. Please do share your love on It started when I came back from the US and broke up with my girl. Then, I started using tinder and had...
Helooo boys, girls, and aunties I’m sameer thanks for your lovely feedbacks and for motivating me to write another story.You can find my previous part at https://www.Indiansexstories.Net/couple/becoming-independent-gigolo/ I’m back again with another story with my client number 2 after becoming an independent professional gigolo. For those who don’t know me, I’m sameer from Mumbai western suburb (mira bhayander). I’m 6.2 feet tall with a muscular body with 6-inch cock size to please any girl or...
Hi there, ISS readers .Kaise hai aap sb. I am back after a long time. With a new story of my gigolo service. I got many emails for my last stories. Thanks to all girls and aunties who replied me. Now I m sharing my latest sex story. Read it out and have fun. And if any girls aunty needs my sex service then you can mail me. There will be total privacy. That’s my mailing id. And boys please stay away from me. I don’t want your emails. I am not going to reply your mails. Now coming to the...