πŸ“š im-just-a-gigolo Part 4 of 1
Part 4
im-just-a-gigolo-ch-4
FIRST TIME SEX STORIES

Im Just A Gigolo Ch 4

Im Just A Gigolo Ch 4

by thors_fist
19 min read
4.81 (5500 views)
adultfiction

In this chapter, Dan talks about the youngest client he ever had, and her young girlfriend who he helped in another way. This chapter contains oral sex, sexual intercourse, some light anal play, masturbating, and sexual instruction and discussion. My thanks to JohnnyGalt for his help. This is a copyrighted work of intellectual property. As such, do not alter, edit, change, or publish this in any way shape of form, including audio, without the written consent of the author. Β© Copyright 2025

I'm Just a Gigolo, Ch 4

My Youngest Client

As you've probably realized by now, I didn't stop escorting women when I graduated from college. I was making real good money, just on the weekends and once I could do it full time, my income more than doubled, even though the demand on weekdays was usually less. I got some week long trips to exotic locations, cruises, trips out of town, and I had to say, no matter who I was escorting, they liked the sex I provided, and were giving me some really nice tips.

This story takes place when I was twenty-nine, so eight years after I started. I could have a 'date' almost any night I wanted one, although I did take breaks from the work from time to time. I was usually in heavy demand and my prices reflected that. I was now making almost double what I'd started at, trying to keep a balance between supply, limited to me, and demand, high.

I was spending the night with a delightful, if somewhat well padded, divorced woman of forty years of age, named Shannon. She usually hired me about once every three or four months to take the edge off.

"Yes, fuck, yes, lick me there. God, you're good with that tongue of yours. My boyfriend wouldn't know how to find my clit if I hung a sign on it. What's worse is he thinks he's God's gift to women. That's right, right there, that's perfect. Don't stop."

My face was shiny from her juices, and since she didn't want me to stop, I didn't, at least not until she'd had three more orgasms, which is when she told me she was getting too sensitive.

"Why don't you tell him what you want?" I asked, resting some between her legs while we both recovered.

"How do you tell a man who thinks he's God's gift to women, that he doesn't know a pussy from a hole in the ground?"

"Very carefully, I imagine," I laughed, "unless you want to hurt his feelings."

"I'm not sure I can hurt his feelings. I've tried to tell him what I like a couple of times, and he just keeps on doing what he wants."

"Why go out with him then?"

"He's pretty nice except in the sack. Just an oversized ego because he thinks his dick makes up for lack of quality."

"Pretty big?"

"Not as big as you are, but more than most, I guess. Do you think you could give him lessons?"

"You want me to fuck you in front of him?"

"Probably not a good idea, huh?"

"Not if he has an ego."

This conversation became prophetic in the future.

"Maybe you could fuck someone else in front of him?"

"It's a possibility, I suppose, but unless he's willing to take direction, will probably fail."

"Are you free in a month?"

"I don't know. I don't keep my calendar. Why? Want to arrange another date so soon?"

"My daughter is turning eighteen in a month. I'm pretty sure she's a virgin, and I'd like you to be her first."

"Why me?"

"Because you're the best, and I'd like her to have the very best her first time. Believe me, my first was a disaster. I wouldn't wish that on anyone."

"Don't you think if her first time is that good, all the sex she gets afterwards will be a disappointment? Shouldn't she experience some average sex instead of getting spoiled right out of the gate?"

"I suppose that could be a problem, but maybe once she knows how good it can be, she can train her subsequent lovers what to do?"

"Like you're training your boyfriend?"

She laughed. "Okay, bad example, but not all men are as obstinate as he is, and I think young men could be very trainable, as they'll do anything to get pussy. I doubt that's changed any since I was a teenager."

"Does she have a boyfriend now?"

"She does, but I'm not sure how serious she is about him."

"Maybe she'd prefer losing her virginity to him."

"I think I can convince her otherwise."

"What day are you interested in?"

"July 22, and I want you with her for two days and two nights, say from six PM on the day of her birthday until six PM on the 24th. Can I get the friends and family discount?"

I laughed. "That's up to Julie. You need to negotiate that with her. Do you want to prepay so I take care of all her expenses?"

"That would probably be best."

I sent a text to Julie asking her to reserve the days in question for a client, and if I was already reserved, see if she could change it, as this was a birthday gift, for a birthday girl. She said she'd take care of it.

"What's your daughter's name?" I asked.

"Fenix, spelled with an FE instead of like the city."

"What's she like?"

"Smart as a whip, National Honor Society, a bit of a bookworm and shy, which is probably why she's still a virgin. She wears glasses. She's taller than I am by about two inches. Very nice figure, although a little small up top. I think she's quite attractive, although I know I'm prejudiced."

"What if she doesn't want to give her virginity to me?"

"I'm sure you can convince her. You're very persuasive with that tongue of yours, which, by the way, I'm desperately in need of again. Get me warmed up some more, then shove that big cock of yours where I need it."

I resumed licking her pussy, giving her another orgasm in the process, before she mounted me in a cowgirl and rode me to three more. She fell asleep in my arms, feeling extremely satisfied. I got a huge tip the next morning.

******

July 22 was a Wednesday this year, so not a real high demand day, but I did have a prior date scheduled for the 23rd which Julie had to move with the promise of a 20% discount. Luckily, it wasn't anything that couldn't be moved because it was only a dinner date.

Shannon didn't want me showing up at her house because her boyfriend would be there, and I was eleven years older than her daughter. Having to explain why Fenix was dating someone much older, and why she would be safe with me, was more than she wanted to explain to the boyfriend, Brad, so I was to pick Fenix up from a friend's house, where she was supposedly celebrating the birthday with her friend, on a two day sleepover.

I was successful enough that I'd bought a very nice car, so I didn't have any problem picking Fenix up. The date consisted of me taking Fenix to a very nice dinner at the Ritz, with a hotel room at the same place, charged to Shannon's credit card. I could charge the meals to my room, and all would be paid for.

The friend lived in a brownstone in Brooklyn. I'd purchased a corsage and seen a picture of Fenix, so I would know what she looked like, so when the friend opened the door, I knew it wasn't her. It was the girlfriend, a slightly plump girl named Svetlana, or Lana for short. She invited me in, and I waited at the door while Lana got Fenix.

When Fenix showed up, she was dressed in jeans and a tee shirt, not at all what she should be wearing to the Ritz on her birthday. She was 5-8, 5-11 with her three inch heels, slim, brown hair worn shoulder length, brown eyes, nice smile, and of course, the glasses.

πŸ“– Related First Time Sex Stories Magazines

Explore premium magazines in this category

View All β†’

I introduced myself, kissing her hand with a slight bow when she extended it. "Daniel Bancroft. I'm pleased to meet you, Fenix."

Both girls seemed impressed with my manners, giggling a little.

"You're gorgeous," Lana said. "Fenix is so lucky."

"I'm glad you think so. We're going out to a pretty nice place, Fenix. Where's your dress?" I asked.

"I totally spaced it out, and since I'm supposed to be having a sleepover, I couldn't go back for it, or Brad would have wondered why I needed a dress. Does this mess up our plans?"

"No, but we'll have to make a stop on the way, so we'll have to hurry not to miss our reservation. Do you have your other clothes?"

"My overnight bag is right there," pointing to a small suitcase beside the door.

"Let's go," I said, picking up the bag.

"Bye, Phenix. Don't do anything I wouldn't do," Lana said. I guess Lana knew exactly what Fenix planned to do.

"Which is what, exactly?" Fenix said.

"Nothing with that hunk," Lana laughed. "I'd do anything he wanted."

"Behave yourself, Lana," I said.

"Do I have to? As soon as you're gone, I'm running upstairs and grabbing my vibrator."

I laughed, put my free hand around her and gave Lana a long kiss. "Think of me while you use it."

"Heavens! My pussy is flooding," she panted when I released her. "You'll have to tell me everything after, Fenix. I'm so jealous."

I tossed her bag in the trunk with my own, and we sped on down the road, headed for Manhattan. The Ritz had a dress shop for just these sorts of emergencies, and it would be quicker than trying to hit one of the department stores.

I grabbed our bags out of the trunk and headed straight to the dress shop, Fenix following behind.

"Yes, sir?" The clerk said. "How can I help you?"

"It's this young woman's birthday. She'll need a little black dress and some lingerie. We have dinner reservations at 7:30, so it needs to be fast. I'm going to check in, and I'll come back to pay as soon as I have my room. I want her to look like a million bucks, but without spending a million. Please take care of her."

"Absolutely. What's your name, miss?"

"Fenix."

"How old are you today?"

"Eighteen."

"Wonderful." She led her to a rack of dresses, and I went to check in.

The bellhop took our clothes to the room. I was already in a suit and tie. I kept the corsage so I could pin it on her dress. I was back within twenty minutes, and Fenix was wearing the cutest LBD. She didn't have a ton of cleavage, but what she had was nicely accented by the dress and whatever lingerie she'd picked out. Her jeans and tee were in the bag.

I stopped as if I was breathless. "You look incredible," I said. "You're such a stunning young woman."

"Thank you, Daniel."

I kissed the back of her hand again. She blushed as I looked her over, appreciating the sight in front of me.

"I have a corsage for you. Is it all right if I put it on?"

"Yes, please."

I stood behind her, letting her feel my presence, reaching around her neck to pin the corsage on the narrow straps above her breasts. I was careful to breathe on her neck, and lightly touch her boobs with the sides of my hands, already searching for those tender sensitive spots she responded too. I knew I'd found some because her nipples immediately perked up in response, making delightful bumps on the front of her dress.

When I was done, I turned her around and admired her again, letting my gaze reflect me looking her over from top to bottom and back, then giving her a light kiss on the lips. After brushing over them, I whispered, "Marvelous."

I turned to the clerk and handed her my credit card. "Thank you for your help. Please add a fifteen percent tip for yourself."

"Thank you, sir."

After getting my card back, I took Fenix's arm and the package of her worn clothes and headed directly to the Contour Gastro Lounge, their in-house restaurant.

"Reservations for two under the name of Bancroft."

"Of course, sir. I understand someone is celebrating a birthday today."

"This amazing young woman turned eighteen today. It definitely calls for a celebration."

"If you'll follow Angie, she'll seat you at your table."

We followed Angie, and got seated at a nice little table. I held her chair, managing to brush both her neck and arm in seating her, giving her goose bumps and keeping her nipples peaked.

"Can I get you anything to drink?" Angie asked.

"If my companion can't drink, I won't either. Water with a slice of lemon and lime, please."

"I'll have the same, Miss," Fenix said. "You can have something, Daniel. I don't mind."

"I would hate to have anything dull my senses, Fenix. I'm greatly looking forward to our date this evening."

She blushed. So cute. I reached across the table and took her hand, softly massaging the back.

"So tell me a little about yourself, Fenix. What are your plans for the future?"

"I'm going to NYU in the spring. Mom and Brad are taking me out to Colorado skiing for a month this fall, and then Mom and I are going to the Virgin Islands this winter, so I won't start until Spring semester."

"Do you have a field of study yet?"

"I'm trying to decide between Medicine or International Studies. I think I'd like medicine, but it takes so long to become a doctor, but I'm also really interested in different cultures. If I take International Studies, I'd like to become a translator at the UN."

"Do you speak any languages now?"

"French and Italian, French better than Italian."

"To satisfy your medical inclinations, would you consider becoming a PA, or does it have to be a doctor?"

"I haven't really considered a Physician's Assistant."

πŸ›οΈ Featured Products

Premium apparel and accessories

Shop All β†’

"My little sister became a PA. It's only a four year degree and she can still prescribe some meds and gets paid a substantial salary. I have some medical appointments where I never even see a doctor, just a PA."

"That's true. Same applies to me."

"Just another possibility."

They brought our water and took our orders for our meals. I didn't want anything too heavy, so ordered a small filet with the vegetable of the day. Fenix had a chicken and vegetable kabob with brown rice. While we ate, I asked her about her friend, Lana.

"She's my BFF from high school, and we're going to NYU together, although she's starting in the fall. When I start, we hope to room with a couple other girls."

"She sounds a little wild. Is she?"

"I think she'd like to be, but she's a virgin like me. She reads a lot of erotica, and she's got all of these ideas of things she'd like to do, but hasn't. She's jealous that Mom bought a date with you for me."

"Were her parents not home?"

"They're in Europe for a month. Well, her mom is. Her parents are divorced. Her mom is in Europe with her lover du jour. She has a regular parade of men going through the house, none of them lasting more than three months. Her dad moved to the West Coast. He does something in TV."

"How old is Lana?"

"She's eighteen. Her birthday was in May, so she's a couple months older than I am."

"What's Brad like?"

"He's nice. Kind of stuffy. I think he'd like to marry Mom, but she says he's a horrible lover. If she married him, she feels like she couldn't be with you anymore, so she's been resistant. They've dated a couple of years now."

"Does he live with you?"

"He's there all the time, but he has his own place. He tries to act like my dad, so Mom will look at him like he'd be a good father to me, and he kind of is. It's why he's taking us skiing in Aspen. Wants to be Dad-like. That's why we had to pull the whole sleepover thing. He'd have shit a brick if Mom told him what she did. Probably would have wondered how she even knew an escort. I do like him, but he's a bit old fashioned."

"Do you feel like your mom cheats on him by seeing me?"

"I suppose a little. They're not married though, and she's not dating anyone else. She said he never gives her an orgasm, and she has dozens with you."

"Does it bother you that your mother has been with me?"

"No. It's not like we're both dating the same person for real. That would bother me."

"Are you a little scared about tonight?"

"A little. Mom said it might hurt at first, but then it would feel so good, I wouldn't care."

"Lana said she uses a vibrator. Have you?"

"Yes."

"If you have, you might have broken your hymen. It might not hurt at all."

"Mom said you were bigger than most guys. Wouldn't that hurt?"

"It doesn't have to. It could if you aren't relaxed, but it's my job to make sure you're relaxed and ready when the time comes."

I held her hand again briefly. Fenix blushed again. She asked about dessert, and I told her we could order dessert from room service afterwards. We'd probably order breakfast from room service too. Another blush.

I charged the meal to our room, and we went up to our lodging, on the fourth floor, with me carrying her package of casual clothes. I handed her a room key, and told her to keep it with her any time she left the room, showing her how to open the door.

When we walked in, she saw the king size bed dominating the room and shivered a bit.

"Do we just get started?"

"No. You won't be relaxed if we just get started. Leave it to me. I'll know when you're ready."

She relaxed a little, just knowing it wasn't going to happen immediately. I handed her the overnighter so she could put her things away, while I did the same. I also brushed my teeth and used mouthwash to be minty fresh when we kissed, and she followed suit. When that was done, I undressed her, seeing the lingerie the clerk had picked out earlier. It was some nice stuff. No bra as the dress wouldn't have looked right with it, just a small, transparent chemise, and lacy booty shorts. She blushed again as I looked at her in her undies, admiring her.

I removed those, and she was naked except for her glasses.

"Have you ever seen a cock before?"

"My boyfriend's."

"I'm a little surprised you're a virgin if you have a boyfriend."

"I probably shouldn't be, but every time his cock gets close to my pussy, he cums. He never got inside of me before he orgasmed. He'd shoot his semen all over me, and then be embarrassed, so embarrassed he wouldn't even make out with me after. He'd go home. The last few times he wouldn't even try. We'd just kiss a little and he'd feel my boobs, then go home. Disappointing really. Are you going to get undressed?"

"Yeah, it's kind of why I asked if you'd seen one before. Didn't want you to be too shocked."

I took off my clothes, hanging up my suit until I was standing in front of her in just my boxer briefs. My dick was half hard already. As she watched, I slowly peeled them down my legs. Her eyes widened when she saw my cock.

"Oh, my. You're much bigger than Ted is. You're not even fully erect yet, and you're bigger," Fenix said. "And you're built. Ted is so skinny compared to you."

"I try to stay in shape."

"That's for sure. Do I need to suck your cock or anything?"

"You don't have to do anything, just go with the flow. Why don't you get into bed."

She shivered again, but she got into bed on her back, parting her legs like we were supposed to get right to it. I laughed.

"Is there something wrong with me? Why did you laugh?"

"There's nothing wrong with you. You're beautiful. I laughed because you think we're ready for sex, and we're not. You're not ready yet. Lie on your stomach, and you don't have to spread your legs. We're just getting to know each other a little."

"You're not going to fuck my ass, are you?"

"I don't think you're ready for that either, probably not any of the first times you have sex. That's for someone with more experience with sex."

"Do you fuck my mom in the ass?"

"I did it once, but she likes it in her pussy more."

Fenix shivered some more when I got into bed and got over her, but she relaxed when I started giving her a massage instead of trying to have sex. I gave her a good long one, lasting over thirty minutes. She was very relaxed when I finished that.

"If it's okay with you, we're just going to kiss for awhile. We don't have to be in any big hurry since we have a couple of days."

"No, I love to kiss."

I lay down beside her and I took off her glasses which she was still wearing, and we started kissing. While we kissed, my hands did some wandering, exploring her body and seeing what turned her on. Quite a bit was sensitive. Her breasts were especially responsive and I wondered if I could get her to cum just from breast stimulation. Something to check out later. She was definitely getting warmed up. Her first orgasm came from fingering her.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like