The Making Of A Gigolo 5 Jill TrimbleChapter 4
- 3 years ago
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Bobby got up from his nap two hours later, when a gaggle of girls stampeded past his room, one of them thumping into his door. He put on the same shorts and T shirt he’d worn when his mother had awakened him, and left the room, to see what was expected of him.
There was cooking going on in the kitchen. A big pot of corn on the cob was boiling, and Prudence was frying chicken, while Mirriam got a ham ready to put in the oven.
“Smells good already,” said Bobby.
“Good, you’re here,” said Mirriam, smiling at him. “Prudence and Constance are staying. We’re going to need more chairs, and she has some at the house. I want you to run her over there and bring them back. She doesn’t need to be carrying chairs in her condition.”
“I told you, I’m fine!” said Prudence.
“Go on,” ordered Mirriam, waving a carving fork their way. “And don’t dilly dally. This all has to be ready in two hours.”
Prudence scooted over, to sit beside Bobby in the pickup. She took his arm.
“I thought we weren’t supposed to dilly dally,” he said, putting his hand on her thigh.
“I’m not,” she said, her voice wounded.
“That,” he said, pushing his arm into the breast she was pressing against it, “is definitely dillying, and this,” he slid his hand up her leg until he couldn’t go any farther, and she hissed... “is definitely dallying.”
“It won’t take long,” she sighed, scooting down into his hand.
They got the chairs to the front door, before she couldn’t wait any longer, and dragged him to the bedroom. Once she was naked, and firmly impaled on his prick, she wiggled her hips furiously.
“I love this so much,” she moaned. She looked down. “Your mother says you do this with other women too.”
“I don’t talk about that,” he said. “It isn’t fair to anyone.”
“Why don’t I care?” she groaned, as a climax washed over her.
“Because, when I’m with you, I only think about you,” he said, pulling at her nipples, to enhance her orgasm.
“We’re not done until you squirt in me,” she gasped, beginning to rock again.
“That’s fine with me,” he grinned, pulling her down to suck at what he had just pulled.
“I love this so much,” she groaned.
The picnic went well, perhaps more so because there were people outside the family there too. Mirriam had gotten surprisingly fond of Prudence, who was almost girlishly thankful that she had a new friend. Further, the girls had all but adopted Constance, who basked in their attention. Bobby’s situation was a little different. That Constance adored him was plain to all the girls. She flirted with him frequently. Mary was old enough to mask her own adoration. Bev paid a lot of attention to him, but was pretty good at making it look like she was just helping with whatever he was doing. Flo was conflicted. She really liked Constance, and the fact that Constance had a crush on Bobby did not escape her. She had been watching Bobby and Bev ever since that night in the pickup truck but, other than what she thought she saw in their eyes, they hadn’t done anything weird.
The younger girls, who, for years, had treated Bobby as any girl treats her big brother, had recently fallen victim to his age and freedom, and their attitudes toward him now resulted in them seeing him as something of a father figure. They vied for his approval, and delighted in any praise he gave them. Flo had seen all of that too.
During the picnic, she watched as Bobby took off his shirt in the shade, to turn the crank on the ice cream freezer. At seventeen, she was plenty interested in boys, in general, but there were none at school that captured her particular attention. There were a few she looked at longer than the others, but they all had girlfriends. Looking at Bobby now, she compared him, for the first time, to other boys she knew. She was both amused, and disgusted to arrive at the conclusion that her brother was head and shoulders above the rest. He was just as handsome, twice as strong, and almost never made fun of her, or teased her anymore.
That kiss had been eating at her. Why had he kissed her like that? It had been a kiss like she’d expect from a boy ... not her brother. And Bev’s hand ... right there in his lap! Mary had told her, the next morning, that nothing was happening that Bev didn’t want to happen ... that Bev was exploring, experimenting with Bobby, instead of boys from school, because she could trust him and he wouldn’t do anything she didn’t want him to do. “You don’t need to be worried about Bobby. He would never hurt any of us or allow us to get hurt. He loves us. That’s all you need to know,” Mary had finished.
She’d thought about that for days. Did Bev want to know what it felt like to put her hand in a boy’s lap? Of course she did. Flo wondered what that would feel like too. Had Bev kissed Bobby, like he had kissed her? What else had she “experimented” with? And how did Mary know all about it? She couldn’t believe that Mary had said that, when Flo was ready, if she was ever ready, she could go to Bobby too! Flo thought about that a lot too. She’d been mildly interested in Joey Stevens for about a month. There had been something about him that made her want to touch him. He’d been friendly to her too, and she let him kiss her once. But he’d picked another girl to ask out, and Flo had backed off, disappointed, but also glad, somehow.
She hadn’t said anything to either Bev or Bobby, and they had both acted like nothing had happened. Bobby had even said it was nothing. How could that be nothing? The kiss, short as it had been, had been disturbing. That certainly hadn’t been “nothing”. Not to her.
Bev left Bobby, at Mary’s call. Mary was freaking about the wedding, and kept thinking up something else every other minute that had to be resolved instantly. Flo couldn’t imagine wanting to get married, but she had already decided that, if she ever did, it was going to be very simple. She’d stand in front of the preacher and say “I do” and whoever the groom was would say “I do” and that would be it. If they had to get married in jeans, that was fine, but there was no way she was going to go completely crazy, like Mary had. She watched Bobby’s muscles move, as he cranked the ice cream. On impulse, she walked over.
“Need some help?” she asked.
“Don’t know if you could turn it or not,” he said.
That was the kind of thing she’d been thinking about it. Any other man would have said, “You’re too weak to turn this,” but Bobby didn’t assume that.
“Why did you kiss me?” she asked. She didn’t think she needed to specify which kiss she was talking about.
“You were upset,” he said softly. “I didn’t want you to do anything that you’d be sorry for later.”
“Why would I be sorry for anything?” she asked.
“Because you love Bev, and you love me, and you would be sad, eventually, if you made trouble for either of us.”
“Are you guys doing it, or something?” she asked.
He looked at her. “Doing it?”
“You know what I mean,” she said. “Christy Bellows got drunk one night on spiked punch. She said she and Charley do it sometimes.” Charley was Christy’s brother, though he was a year younger than Christy.
“And you believed her?” asked Bobby.
“Yes,” said Flo. “She kind of described it in detail. I’ve heard of other kids messing around with their brother or sister.”
“No, we’re not ... doing it,” said Bobby.
“Why did she have her hand on your cock?” asked Flo.
“When did you start talking with a gutter mouth?” he asked.
“Don’t give me that crap, Bobby. Cock, penis, prick, whatever you want to call it ... she had her hand on yours.”
“Why do you want to know this?” he asked, his arm steadily cranking.
“I don’t know,” she said. “It makes me nervous, thinking about it.” She frowned. “If you’re doing stuff, I mean.”
“Why would you be nervous?” he asked.
“I’ve kissed exactly one guy,” she said, folding her arms under her breasts. Flo was smaller than either Bev or Mary. She was a tomboy, and had the shape to go with it. “When you kissed me, it was better than it was with him. That’s just weird.”
“He didn’t love you,” said Bobby. “I do. It makes a difference.”
“She’s younger than I am,” said Flo, ignoring his comment, even though it had sent a zing of emotion through her. “How come she gets to do stuff, and I don’t?”
“Do you want to?”
“No, but it’s not fair anyway.”
“Why do you even care what Bev does?”
“I’m her big sister,” said Flo. “I have to watch out for her.”
“Then I think you should ask her if I’ve done anything that makes her nervous, or afraid, or worried, or in any way that might cause her pain.”
“That’s a bullshit answer,” she said.
“You’d better be careful,” he warned, stopping the crank. “If Mamma hears you talking like that, she’ll wash your mouth out with soap.”
“She would not!” said Flo, feeling suddenly like she was ten again.
“And I’d hold you down while she did it,” said Bobby.
“Why won’t you just tell me?” she moaned.
He stopped cranking and looked at her. “Let me ask you a question,” he said. “How would you feel, if I told, say Horace, that I kissed you?”
“I’d die of embarrassment!” she wailed.
“Then why are you asking me to talk about Bev?”
“So you’re not going to tell me what you two do?”
“Nope,” he said. “Ask Bev. If she wants to tell you, that’s fine. If not, it’s between her and me.”
“Are you going to kiss me again?” She blinked. Where had that come from? She hadn’t intended to ask him that.
“If you want me to,” he said calmly. He started cranking again.
“That’s the most ridiculous thing I ever heard you say!” she whined. “Why on Earth would I want you to kiss me like that again?”
“There isn’t anybody in the whole wide world that can answer that question except you,” he said. He grinned.
She fumed for a minute.
“Did you like it?” she asked.
“Kissing you?”
“Yes ... did you like it?” She seemed very interested in his answer.
“I already told you ... I love you. I wouldn’t have kissed you if I didn’t love you.”
“But you’re my brother!”
“I’m your half brother,” he said. “You know that.”
She looked around, a horrified look on her face. “We don’t talk about that stuff!”
“But you know it,” he said.
“You’ll always be my brother,” she said stiffly.
“And I’ll always love you, whether I ever kiss you like that again, or not,” he said. “You want to try this now?”
He stepped away from the churn, and she moved to grasp the handle. She gave a lurch. The crank wouldn’t budge. Her eyes widened. He had just been turning it ... round and round! She tried again. She got it to move half a crank, before giving up.
“Think about this, before you spout any more dirty words out of those pretty, soft lips of yours,” he said.
He leaned over and started turning the crank again. She watched his muscles bunch, and felt flutters in her stomach.
“I can hold you down, while Mamma washes your mouth out with soap.” He grinned.
She stalked away, trying to be mad at him. It didn’t work, though. Just like always, he had treated her like an adult, instead of a little sister. True, he hadn’t answered all her questions, but even that, she couldn’t really argue with. She’d heard boys boasting about what they’d done with certain girls. That was one of the reasons she never did anything with any of them. They had big mouths.
Prudence and Mirriam sat in lawn chairs, in the shade of the elm tree and watched, as the young ones played, ran, or shot off firecrackers.
“Your children are so well behaved,” said Prudence.
“You don’t see them all the time,” snorted Mirriam.
“Yes, but what girl just stands and talks to her big brother, like Florence was just doing? Most girls don’t want to have anything to do with their brothers.”
Mirriam nodded. “They didn’t either, until he left school. He’s grown up so much. I’m really lucky he’s still living here. He does a lot of work.”
“I could watch him crank ice cream all day long,” sighed Prudence, watching his muscles work.
“I could too,” sighed Mirriam. She blinked, and looked at Prudence, who was grinning at her. “I didn’t mean it that way!” she spluttered.
“Yes you did,” said Prudence, still grinning. “And don’t deny it. He’s gorgeous, and any woman would see it, even his mother.” She giggled. “Besides, I don’t feel as guilty when I know that another woman twice his age gets all googly eyed over him.”
“I am not twice his age!” said Mirriam, trying to sound stiff.
“You’d feel like it after he got through with you,” laughed Prudence.
“Prudence Harris!” gasped Mirriam. “I am shocked!“
Prudence saw the flush of pink under Mirriam’s chin and leaned toward her, lowering her voice.
“He can go for an hour, if you let him.”
“I will not listen to this!” moaned Mirriam.
“One day we did it four times in less than three hours,” giggled Prudence.
Mirriam covered her face with her hands.
“Why are you doing this to meeee?” she moaned.
Riding in the back of the pickup with four sisters was something Bobby had done many times. The two youngest sat up front with Mamma, who drove. Mary was going to be delivered back to the house by Fred, who had his own car. Her days of curfew were over, now that she was engaged, and the wedding was only a week away. He found himself sitting between Bev and Flo, all three of them sitting with their backs against the cab. It just seemed natural to put his arms around them. Bev was on his...
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On a warm summer’s eve On a train bound for nowhere I met up with the gambler We were both too tired to sleep So we took turns a-starin’ Out the window at the darkness The boredom overtook us, he began to speak He said, “Son, I’ve made a life Out of readin’ people’s faces Knowin’ what the cards were By the way they held their eyes So if you don’t mind me sayin’ I can see you’re out of aces For a taste of your whiskey I’ll give you some advice” So I handed him my bottle And he drank down my...
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...
Hello to all the reader of ISS. Hi Girls / Ladies / Housewives of Rourkela Odisha, I am Bapi from Rourkela, Odisha. I am back here to share one more incident which took place recently. 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 sexual life or just for...
Hi guys, this is Jerry. I am very young guy from Bangalore and writing this story for the first time. I work at an MNC, but also offer my services as a male companion. I am thick where I should be, my tool is about 7″ long. Average but young body. I got a phone call after putting up my ad on personal listing for several days. She was stuttering while speaking. She told her name as Mahima. She is 35 years old, but decent sized boobs and tight ass. She asked me about myself and told she wants to...
Hi Everyone, I want to post this story that happened to me recently and how I became a gigolo. Actually this is my second story and this all happened because of the first encounter with neighbor. Luckily she only made this opportunity for me. So this encounter is with one of her friend(don’t want to tell her name tho) who also working in Pune. I came to know about her from my neighbor that she is a widower and her husband died long ago. So my neighbor aunty told me that her friend really is...
Hello everyone, I am Avinash and basically from Hyderabad. I do provide gigolo services for women (Hyderabad and Bangalore) and especially i love matured women of all sizes.(plump, medium or skinny) Let me tell you a story which made me a gigolo for fun and not for money. I recently came back from UK and I am self-employed.I am pretty successful in my business and as a successful entrepreneur I do attend conferences and meetings. In that process there was a business meet early this year at...
My name is Rahul and I’m from Ahmadabad. I’m new to ISS. Recently I came to know about iss and I became big fan of this blog. Now let me start with my story. Its about fulfilling my fantasy for real. I always fantasize about having sex with young bhabhis but being a was afraid of asking any of them. Finally I found a way to enjoy with them by becoming a gigolo. I knew the pickup points in the city and hence I went there wearing red t-shirt (usually that is the signal for being Gigolo). I waited...
Hi all ISS readers, my name is Adam & this is going to be my first story here hope you like it. Mai apne baare me bata deta hun, mai Delhi me reheta hun 5.8ft tall, age 25, with 7 inch cock fair with a good body and good stamina aur mai part time modelling bhi karta hoon, meri expertise Massage service hai, jo ki mere sabhi cleints jaante hai, main ek gigolo(call boy) hoon or females ko body massge or sex services provide karta hoon, meri cleint jiske baare me ye story hai bhot he zada sexy...
Hello ISS readers, this is Vijay from Chandigarh – The city beautiful. Main ek gigolo hu, ek professional gigolo, meri 24 yrs ka 5.8 height aur athletic body , dkhne mein average hu. Yeh meri true story hain jo main aaj aap logo ko bataunga aur meri life ka first exp bhi, aur yahi se meri gigolo banne ki shuruwat bhi hui. Dosto yeh meri frst story hain, jo main likh rha hu isliye age mujhse koi galti ho jae to apne is dost ko maaf kar dena aur job hi galti ho usko btana taaki main next time...
It was a different Judy I held in my arms. She was not the loving, sweet, and cuddly Judy tonight. She had changed to a voracious female animal that demanded to be possessed. There was a wildness about her that I had never experienced.I had felt it as she walked in the door. She didn't close it, she slammed it shut. She did not wait for me to embrace her and welcome her back from her sightseeing tour, instead she crushed me to her, practically ripped my clothes off me. She wouldn't let me...
MatureHi everyone for myself i am john from ahmedabad. 24years old goodlooking man. I am presently do the gigolo job and share my great experiance in this job first time mai jab 16years age ka tha tab ek padosi bhabhi se baatchit chalu hui thi tab woh waha nai aai thi aur woh divourses thi usne paheli baar muje uski bahen ki sadi me sath me le gai thi tab hame waha 2din tak rukne ka tha sadi puri ho gai aur dusre din subah ko hame nikalna tha lekin sadi ki raat ko hi muje usne kaha kya tum sexy ho...
Now it was the month of September. As I told you all, I have temporarily lost my job. I needed one as I realized that I couldn’t depend upon the profession of a Gigolo alone. I decided that I would also do something else to have full-time employment. Working as a gigolo will add to my income and be a source of my fun. I searched for a job and got one at a call center. I joined that job and started to work. The pay was less, but the chances of incentive were great. As I joined this job, I...
I started my working life working in a store, where my gift of the gab won customers of both sexes over and made me popular with my work colleagues. I was not an adonis, but from starting my working life I began to make the best of myself by starting a exercise regime and buying good clothes and beauty products, and discovering sex. I started paying escorts for sex so that I could enjoy a range of uninhibited sexual fantasies and kinks that I had. And professional escorts for a fee were...
It was the end of the summer, and I was facing the prospect of returning to school. Dammit, I was making so much money as a gigolo that I hated the thought of what going to school was going to do to my working schedule. I now had enough older clients lined up that I was fucking them five days a week at a usual price of $200 per day before Jenny's share. The thought of losing $875 a week, plus all of that fucking that I would be missing, really had me in the dumps. Furthermore, I was dating...