AUNT CATHY’S GIGOLO

I served my country honorably until I took a shot to the hip. Not much an Army Ranger can do without a useable hip. I was patched up pretty well, but still given a medical discharge, some very nice VA benefits, and decided to go to college full time. In my four and a half years of active duty I managed to get a full year of college.

My Aunt Cathy runs a hair salon from her home about four hours from my parent’s place. About ten minutes from her house is a university I’d always wanted to go to, and was accepted at, so I was happy when I received an e-mail from her telling me I could come stay with her for free, all I had to do was mow her lawn and pull a few weeds.

Aunt Cathy has always been my favorite relative. She’s slightly overweight, has a 38D-30-38 figure, a bubbly personality and laugh, and fun personality. I’m a bit shy but she could always draw me out. When I arrived at her house in my Nissan Frontier pickup she ran out and nearly knocked my over with a hug. She gave me a choice of bedrooms (except the master) and treated me like royalty.

The next day, after I registered for classes, I went to the single seat hair salon and found Aunt Cathy doing the hair of a lady about forty years old. I had seen a nice Mercedes in the driveway and figured it was a customer’s (or client as Aunt Cathy calls them). The lady had expensive looking shoes and jewelry, and knowing what Aunt Cathy charges, I figured the lady was very well off. I told my aunt I was back home and was going to grab something to eat from the fridge.

About 45 minutes later Aunt Cathy came to me and asked to talk. At first I thought I had done something wrong but she set those fears aside. “Drew, some of my clients are quite well off financially, but lonely. Take Mrs. Porter for instance. She has plenty of money, but is, shall we say, lacking in companionship.”

“Do you mean she hasn’t been laid in a while?” I asked.

“Yes, and she was asking about you.” Aunt Cathy wasted no time getting to the point.

“Me? She’s what, 42, and I’m 23.”

“Drew, she doesn’t want a boyfriend. She just wants to get laid. And she’s willing to pay for it.”

“Really? How much?”

“If you want to do it, that would be up to her and you.”

“You don’t mind? I mean, I’m living with you.”

“We aren’t screwing, and you’re a healthy young guy. If it wasn’t for Jim I’d screw you.” She laughed heartily. Jim is her boyfriend. “Also, Mrs. Porter said she has friends like her, needing to get laid.”

“I…uh…don’t know what to say.” Truth was, I hadn’t had sex in over a year.

“Why don’t I send her back. My next client is here, and so I’ll tell Mrs. Porter to come back and use the tanning bed.”

Mrs. Porter came back. I thought it would be an awkward moment but she sat on the couch and got to the point. “My husband is in prison for tax fraud. I haven’t had sex in two years. I’m anxious to solve that problem. I think you’ll be discreet, and you look healthy. Would you be willing to help me?”

“I’ve never done this before.”

“What, had sex?”

“No, I mean with someone I don’t know, and for money.”

“I haven’t either. And listen, most of my friends are like me, well off Jewish women whose husbands or ex-husbands are professionals, and we lack sex. I can, shall we say, keep you happy and busy.” I remained silent for a few seconds thinking about it. “Are you interested?”

“I think so. But what if I don’t…please you?”

“Do you have a penis?”

“Well, yeah.”

“Do you like to eat pussy?”

“I love to.”

She opened her purse and removed six fifty dollar bills. She set five on the coffee table and held the other in her hand. “I’ll give you $250 to eat me and then fuck me. If you give me an orgasm I’ll add this extra $50. Shall we go see if we’re…compatible?”

We went to my room. Michelle, as she told me to call her, was wearing a very expensive looking dress so I took a hanger from my closet and handed it to her. “Very thoughtful of you,” she said. She turned and I unzipped her, then picked up the dress as she stepped out of it. She took her shoes off as I hung the dress up. I then unclipped her bra and set it on my desk. Her legs were tanned and I was surprised she wasn’t wearing hose. “Now for you,” she said and she removed my polo shirt. I stepped out of my shoes, then she opened my belt and pants and I stepped out of them. We both stood in our underpants. Michelle lay on my bed and pointed to her pussy. “Eat me first.” I knelt on the bed and pulled her panties off. She was fairly hairy, something I’m not used to, but she wasn’t expecting to have sex.

I laid down between her legs and moved them over my shoulders. I began by licking her several times from anus to clit. She cooed and wiggled and I knew I was pleasing her. What they say about sex and riding bicycles must be true. I then stuck first one finger and then a second into her and found her G spot right away. Her butt and back came off the bed and her pussy muscles squeezed my fingers. “Oh, come on, put your cock in me!”

I took my briefs off and lined my cock up and slowly fed it into her, but she would have none of the slow stuff. She put her feet around my ass, lifted her pelvis, and pulled me in. “Don’t pound me, but give it to me firm.”

“Where do you want me to come?”

“In me. I can’t get pregnant.”

I started sliding my seven inches in and out slowly but firmly. She sped me up with foot pressure on my butt. Soon she was moving her head from side to side saying, “Oh yes, oh god, oh yes.” Then her pelvis lifted and she began ramming into me. I felt my load starting to move up my prick. “I’m going to cum soon,” I told her.

“Good, I’m read y for you.” I moved my hands under her and grabbed her ass and really went deep. Soon I rammed deep and let go a large load, and as I did Michelle let out a load groan. And her pussy gripped me like a fist closing around it.

A few minutes later I lifted up and looked Michelle in the eyes. “I hope I made you happy.”

She smiled back at me. “You certainly did. You earned the extra $50, and then some. Can you do once a week?”

Four days later, on Friday, my second day of classes I was sitting in the kitchen when Aunt Cathy came in from her salon. “You got a call from a lady named Leah. She’s a friend of Mrs. Porter. She asked for an appointment for tanning, when you’ll be here.”

“Do you know her?”

“Yes, I do her hair once or twice a year. Very pretty lady, younger than me, maybe 35 years old.”

“This doesn’t bother you?”

“Are you kidding? I’m jealous.”

“Jealous? You know what mom and dad would say.” Aunt Cathy laughed as she walked back to her salon. I called Leah and she asked if I would be there in an hour.

An hour later I saw a black BMW pull into the driveway. A few minutes later Aunt Cathy walked Leah into the main area of the house. I was dressed in dockers and a nice shirt. Leah was wearing a nice pant suit. She stood about 5’8” tall, had small breasts, blond hair and a big smile. “Are you Drew?” she asked.

“Yes,” I replied.

“Michelle Porter is a good friend of mine. She told me you made her cum three times in one hour. My husband is sixteen years older than me, works long hours, and hasn’t pleased me in years. He usually cums as soon as he sticks it in me. I’m not love starved, but I’m orgasm starved. Think you can help?”

“I can try my best for you.”

“What do you charge?”

“I don’t know. Michelle was the first person I did that with. Why don’t we first see if I can help you.”

She shrugged. “That’s good customer service.”

I led her back to my room and shut the door. She unbuttoned her suit jacket and kicked her shoes off. She was doing things quickly. “Leah, slow down. Let’s relax and enjoy our time.” I stepped up to her and began unbuttoning her silk blouse. She reached up and unbuttoned my polo shirt. As I mentioned, her breasts were small, probably an A cup, but as soon as I touched her nipples she moaned and told me her breasts were sensitive and she liked breast action. I unhooked and lowered her pants, then removed her pantyhose, and sat her on the bed. She then undid my belt and pants and lowered them. “What do you like, Leah?”

“Oh, I love my breasts played with.

They’re small, so my husband tends to ignore them.”

I removed her panties and my shorts. She started to get on the bed and I asked her to wait. I laid down and then had her straddle me over my abdomen. I reached up and pulled her down, taking one of her breasts into my mouth wile palming the other. She twitched and made sounds telling me she was pleased with what I did. After about five minutes she scooted back a little and put my cock underneath her, with it laying flat against me. She started rubbing her pussy over it and I could feel she was very wet. “Oh, you’re making me feel so good, so good.” Her rubbing against my cock felt good to me too. Soon she shuddered, squealed, and released a flood of juices on me, then collapsed on me. “Shit, you weren’t even inside me yet and you made me cum.” She lifted her head and looked in my eyes.

“I’m glad I could please you.”

“Please me? You gave me the best orgasm I’ve had in five years, maybe more.” She lifted her pussy a little, grabbed my cock, and inserted it into her pussy. “Since you didn’t cum we can go again, can’t we?” She raised up and I took one of her breasts in my hand. She began a backwards and forwards movement rather than up and down. I used my other hand to rub her clit. “Oh, what are you doing to me?” She moved like this for a couple minutes then asked if I was close.

“Not really, the back and forth doesn’t do much for me.” She then started going up and down on me. I let go of her breast and grabbed her hips. I could feel the cum start to boil on my sack. Leah put her hands on my shoulders and huffed louder and louder. I reached back with one hand putting it on her ass cheek, and rubbed my middle finger on her anus. She looked into my eyes and grinned. I put the tip of my finger into her star and did an in-out motion. Within a few seconds Leah stiffened, arched her back, and squealed loudly. She again flooded juices, enough that they flowed out around my cock. She laid on top of me. I spread my thighs, which caused hers to spread and started spearing into her.

“I’m going to cum again, I’m going to cum again,” Leah said. “Can you cum with me?”

“Do you want me to cum in you?” I asked.

“Yes, yes, yes,” she said.

“Here I cummmm” I said as I pushed as hard as I could into her, and jammed my middle finger deeper into her ass. Leah bit my shoulder as she stifled a scream. I could hear her snorting through her nostrils as her orgasm rolled through her. I could feel our combined juices flowing out of her and down my ass crack, and they felt hot.

Later as Leah was getting dressed she handed me $500 and said, “That’s the best sex I’ve ever had, and for damned sure don’t mind paying for it.”

“I’m glad I could make you feel good.”

“You made me feel great. Do you mind meeting periodically?”

“Sure. Just give me a call, either here or my cell phone.” I wrote the numbers down for her.

“May I refer a friend or two?” I nodded.

A SURPRISE

One day as I neared Aunt Cathy’s house on my way home from classes, Cathy called my cell phone. “Are you coming home soon,” she asked.

“I’m about five minutes away. Why?”

“There’s…someone here to see you. A new client, I think.” I hadn’t called Michelle, Leah, or one other woman I was paid to have sex with clients. I hadn’t called them anything really. But Aunt Cathy sounded concerned. “I’ll be right there.” She asked me to come to the salon. When I drove up to the house there was a car in the driveway. I entered the salon to see Aunt Cathy talking with a woman about thirty years old, blond hair, in good physical shape. She had a…serious look to her – sort of like a soldier, but not the thousand mile stare. She was about 5’3” and very pretty. Her hair was cut in a… practical way. What was in about her?

“Drew, this is Celeste. This is the first time I did her hair. She’d like to talk to you.”

“Drew, I’m a police officer. But I’m not here to arrest you.”

I swallowed. And sweat. “OK, what can I do for you?”

“I’ve been friends with Leah for years. She told me about your…services. She told me because I haven’t had a man in about three years. I’m here as a customer. I’m willing to pay you.”

I looked at Aunt Cathy. No wonder she had sounded concerned. “How do I know you won’t arrest me and Aunt Cathy?”

“Because I am soliciting you. I’m asking you. I can’t afford what Leah paid you, but here,” she pulled $300 out of her pocket, three crisp one-hundred dollar bills.” “I haven’t been fucked for so long, and I need someone I don’t work with. I have a hard time making friends with men when they hear I’m a cop.”

I thought for a moment. “Can we take this discussion away from my aunt’s salon?”

“Wherever you want.”

We moved into the livingroom of the house. Celeste put her purse down and looked around. She then said, “I can prove I’m not here under false pretenses.” She knelt down in front of me, opened my belt and pants, took my cock out, and started sucking on it. She then looked up at me and said, “There, I initiated the action.” None of the other women gave me a blow job, but then they were paying to be pleased. Celeste worked hard at it, and she was damn good, but I was still concerned and nervous. After several minutes I was only half hard, and she was looking frustrated. “What else do I need to do to convince you?”

“I think I’m convinced. Let’s go to my room.” Considering my line of work I had done my room up nicely and put in thick curtains for privacy. I also had a nice Bose sound system installed. I turned on the floor lamp and turned to Celeste and pulled her to me giving her a big hug. That helped calm her. I help her for a couple minutes then started unbuttoning her shirt. She turned so I could do her bra, and after removing that I again held her, my front to her back, and palmed her tits for a while. I then moved one hand down inside her pants, finding a bare pussy, and gently rubbed her clit gently. After a minute or so of this I opened her pants and let them drop. Celeste kicked off her shoes and pants, then lowered her panties. I led her to the bed and began removing my own clothes while she watched. After I was undressed I crawled onto the bed.

Celeste backed up to me, which confused me until she said, “Before you fuck me, I’d like to feel you rubbing your hands on me like you did before.”

“Sure, whatever you’d like.” She put her top leg over me while I slid an arm under her. I used both hands to gently squeeze and hold her breasts, lightly pinching her nipple. I then moved one hand down to her pussy. I felt a trimmed bush which covered only the top portion of her vulva. She spread her legs more and I inserted a finger into a very wet and warm vagina. Celeste hissed and moved her hips in a circle obviously enjoying my actions. Soon I inserted another finger.

“That feels so good.” I was able to lower my head and nibble her ear. She reached up with her upper hand and held my head. With my two fingers inside her and my thumb rubbing her clit her pelvis began moving faster and she soon launched into an orgasm. I could feel her body get warmer, her hand pull my head harder, and her hip circles became a back and forth motion. “Don’t stop, don’t stop,”became her mantra, and then she thrust her hips up and inhaled sharply. “Ugghhhh,” came out of her in a coughing like sound.” She lay back against me, too my hand from her pussy, reached back for my steel-stiff cock, and lined it up with her pussy. She dug her heels into the backs of my thighs as she pulled herself down onto my cock. “Go ahead and rub my clit and tits,” she instructed. Who was I to argue with a cash customer? I remained still as she provided the in and out motion. “When you’re ready I want you to cum in me, OK?” she asked.

“I will,” I replied, and it wasn’t going to be very long. Celeste seemed to be building up to her next one quickly, and I was getting close.

“Pinch my clit!” She seemed to exclaim it. I pinched it between my thumb and index finger and her pussy gripped me tighter. Her body seemed to heat up ten degrees and her juices flowed from her pussy. “I’m cumming, I’m cumming,” she cried. As she stiffened I shot several spurts of cum deep inside of her. I could feel the tip of my cock hitting her cervix and she inhaled deeply and stiffened each time I hit deep. We started coming down from out plateau though she continued holding me with her heels. I wrapped my arms around her under her breasts. I could feel Celeste swallowing and breathing deeply.

“I…I would like to come back…from time to time, but I don’t make as much as the rich women who… use your services.”

“That’s OK. I can make discounts for those who protect me.” We got dressed and I walked Celeste to the door. Before I opened it she turned, gave me a hug, and then kissed me on the lips. She was the first to kiss me.

Later Aunt Cathy came in and asked, “How…was Celeste? Legitimate?”

“You know, she was. And she really needed me.”