I’ve been overwhelmed by the comments on the first chapter of Aunt Cathy’s Gigolo. Since I started writing it over a month ago (college students, and gigolos, have busy schedules).
I was sitting in class when my phone vibrated in my pocket. I checked the text and it was from Aunt Cathy. It read, “Have an interesting client here for you. When will you be home?”
I texted back I’d be home in forty minutes.
When I arrived there was a woman sitting in the livingroom of the house. She stood as I entered and asked, “Are you Drew?” She was medium height, thirty five or so years old, long black hair, medium boobs, dark complexion, manicured nails.
“Yes, I’m Drew.”
She held her purse nervously in front of her. “I’ve heard about your…business.” I stood looking at her but said nothing. “I’d like to, how do I say it, hire your services?”
“How did you hear about me?”
“From one of the ladies in my congregation. I’m their rabbi.”
“I’m not religious, but this seems…different. Are you sure you want to do this?”
“Just because I’m a rabbi doesn’t mean I’m not sexual.”
“I understand. I wasn’t trying to judge you. I was thinking more of if this gets found out. You could lose your position.”
“I have thought of that. I’d like to take you on a short trip out of town, about an hour away. Overnight. I’ll pay for your time.”
“I can do that. Tonight?”
“Can you go tonight? I can make reservations at a hotel I like.”
“I don’t have classes tomorrow, but I have a test the day after. I’d like to get back early enough to study.”
“I can do that. And, you can study while we’re there, I won’t mind. But there is one thing I’d like to ask.” I nodded. “I’d like…I’d like to not be treated like a…customer. I’d like to be…romanced a little bit, if you can?”
“I will try to do my best. But, I don’t know your name.”
She looked down like she was thinking about it. “Beth, my name is Beth.”
“Beth, let me change. I’ll put on some nice clothes, and throw together a bag.”
“I’ll be back for you in an hour.”
Beth picked me up an hour later in an amazing dark-blue BMW. She had changed into a pretty dark red dress. Her eyes were sparking and her smile was relaxed like she was going on a date with someone she was in a happy relationship with. “I was married for four years, to a chiropractor. But he couldn’t handle playing second fiddle in the congregation. He took off with one of the single women. That was three years ago, and I haven’t been on a date since.”
“I’ll do my best to make this seem like a great date for you.” I meant it.
“Do you mind if I ask you about you, like what you’re studying?”
“That’s fine. I want to major in history, but what do you do with a history major?”
Beth was amazing as she answered. She was merging onto a busy interstate and didn’t miss a beat. “I suppose you could write about history, or teach history. Or use it to build on an advanced degree in law or theology.”
“I hadn’t thought of those.”
“My undergrad degree is in art history.”
We arrived at what looked like a resort. Beth went and checked in since she was using her credit card. We then drove out to a building set overlooking a lake. Beth released the trunk from inside the car. I went to remove the bags, surprised to see her at the trunk. “Dear, you go in and freshen up, I’ll carry our bags in.” She looked in my eyes, surprised, and smiled. She turned and headed into our suite. I carried our bags, including her fancy Italian leather, into the room and closed the door. As I entered she was hanging her dress in the closet, wearing a long slip. She took a robe and headed for the bathroom. “I’ll take a quick shower.” I nodded and she closed the bathroom door. A couple minutes later she opened the door a tiny bit and called to me. “Drew?”
I walked to the bathroom where I could she her head. “Yes, Beth?”
“I want to know…do you like prefer ladies shaved, or…not shaved, or somewhere inbetween?”
“Beth, I prefer….” I held my hand out to the door opening.
“What are you…?”
“Let me have your hand.”
“My hand?” She stuck her right hand barely through the door. I took it and gently pulled her out of the bathroom. She was naked. She was looking directly into my eyes. I pulled her to me and wrapped my arms around her. Her arms went around my back and she held me close. We could feel each other breathing. After about three minutes of holding each other she said, “You didn’t even look…down there.”
“No, I didn’t.”
“So, you don’t care?”
I picked her up and carried her to the bed. I laid her on it and stood back looking into her eyes. I then leaned down and gave her a soft, gentle kiss. As I kissed her I reached down and massaged her breast. Then I moved down and gently sucked on her nipple, then switched to the other. I literally made love to her breasts. I still hadn’t looked at her pussy. “Drew, can we take your clothes off?” I stood up and began unbuttoning my shirt while she undid my belt and pants. I kicked my shoes off and soon I was naked too. She grabbed my cock and gently rubbed it up and down. “I…I like giving oral, but I don’t really like giving it. Is that alright with you?”
“Certainly, Beth.” I laid down on the bed and rubbed her breasts again. She held my cock in one hand as she put her other behind my head. Her nipple was rock hard. I moved one hand down slowly to her pussy. Beth rolled onto her back and spread her legs. Her bush was thick but trimmed. She was warm and wet, and that was determined before entering her. I spread her lips, which were thick and long. When I got to her entrance I entered slowly, circling with my middle finger as I rubbed her clit with my thumb. Her hips drove up slowly trying to engulf my finger quicker. I gently bit her nipple while fingering her pussy, and her breathing deepened and quickened. Both of Beth’s arms went around my head. Her heels moved closer to her butt and her knee’s dropped open wider.
“Oh, that feels so wonderful.” I sped my motions up and her hips moved up and down in time with my middle finger, joined by my ring finger. A couple more minutes and she, “Oh, oh, I’m going to….” She stiffened and froze, then gave a sharp exhale as her body relaxed. Her arms only slightly relaxed their grip around my head. “Drew, I want you to enter me, to make love to me.”
I lifted my head slightly and looked into her eyes. “What do you want me to do when it’s time for me to cum?” I gave her a gentle kiss.
“Cum inside me. I’m safe, my period ended two days ago.” I moved to between her legs. She stiffened as the head of my cock made contact with the entrance to her vagina. “It’s been a long time, and you’re bigger than my ex-husband, please be gentle.” Beth put her hand on my hips to control my movement. I slowly moved into her inch by inch. When I was halfway in she had me stop for a moment. “It feels so right, but I am being stretched.” I lowered my head and took her nipple in my mouth and started nibbling. She arched her back and pulled me in more. Soon she had a slow rhythm set and I could feel my cum charging up my cock, which felt like it was being squeezed by a virgin. Beth’s pelvis began moving rapidly, her arms wrapped tightly around my back, her breathing labored, and we both crashed into a long and satisfying climax. After I shot my load Beth locked her heels together behind my ass and held me still for quite a while, which was fine, I was quite content there.
After we showered we went to dinner then walked along the lakeshore arm in arm. I learned Beth was an accomplished musician and painter, but quite a lonely woman which she attributed to her position as a rabbi. I told her my history professor was someone I thought she would enjoy getting to know, and I knew he was Jewish from some of the talks we had. She laughed and said, “I’d love to meet him, although I may already know him since there are only three synagogues in this town.” We set it up that I’d ask if he’d talk with Beth about being an adjunct professor since he had previously been an adjunct.
When we got back to the room we snuggled as we watched a movie, then went to bed. Beth was very direct in what she wanted. “I want you to make love to me from behind, and I would like to fall asleep with you inside me. Can we do that?” I turned her shoulders so she faced away from me, and had her recline against me, pulling her top leg over mine. She was wide open, and when I felt her pussy she was quite wet. I fed my cock into her, and fingered her clit with my upper hand while massaging het tit with my lower. “I am so close already,” she said. She planted her feet flat and moved her pussy back and forth on me. I stopped thrusting as her movements were uneven. She soon had a medium orgasm, then began moving again. “I want another, I need another….” She moved even faster. “Are you almost there?” she asked.
“Stay inside me after you cum.” Her breathing became raspy and hoarse and her body temperature rose what felt like ten degrees. My cum began a rapid journey and I was reaching my peak when she jammed her pussy down hard, stiffened and grunted. I shot my thick load deep inside her. She took my fingers from her clit quietly saying, “Too intense.” After a few minutes she brought her upper leg down and we rolled into a spoon position and fell into a satisfying sleep.
The next morning we made love twice more before returning to town. I did introduce Beth to my history professor. Beth used me one more time, about six weeks later. Then she and the professor began a relationship. A year later I was invited to the wedding.
I was just sitting down to lunch when my cell buzzed that I had a text message. I opened it and read, “Are you available today? I NEED your services. Celeste.” I texted back, “No classes today. Come on over.”
BACK TO CELESTE
Celeste entered through the salon on the pretense of using the tanning bed. “I need a good hard fuck. I just got my ass chewed by my supervisor for something that wasn’t my fault.” I’ve never seen a woman strip as fast as her. I motioned to the bed and she shook her head no, “You lay down, I want to be on top.” Fortunately I was hard. She straddled my pelvis and lowered herself halfway down then stopped. “Can you believe this shit? The lieutenant said I was being too aggressive with suspects.”
“What?” She was talking about work while we are having sex?
She rammed herself the rest of the down on my cock. “Lt Harrison said I was being too aggressive with suspects. I’m not quite 5’3” tall, busting perps over six feet, and I’m being too aggressive.” She began a vigorous back and forth movement, and then stopped. “It’s not my fault the city doesn’t hire more cops so we have more to back us up.”
“Your safety should be his primary concern,” I said as I raised and lowered my hips a couple times.”
“Fuckin’ right about that.” She lowered her head and put her hands behind my neck. “Pound me good.” I grabbed her butt cheeks and began a serious pounding of her pussy. The harder I thrust the more she gripped me, seeming more satisfied. I moved my right hand around her, wet my middle finger in her juices, and stuck it halfway in her ass and moved it in rhythm with my cock. She lifted her face and looked at me. “You’re not sticking your dick in there are you?”
“That’s just for stimulation. I wouldn’t do you there unless you asked me too.” Celeste lowered her mouth to mine and we shared a hard kiss, our tongues like dueling swords. She suddenly raised her head a bit and began shaking like she was having a seizure. Her chest reddened and I felt a gush from her pussy.
“I want to roll over now and have you really pound me.” Her voice was softer, and she seemed content despite the request. Without withdrawing from her I rolled us over. I gave her long, deep, fast strokes. “Bite my tits” she commanded. I reached down and took her nipple in my teeth and gently bit down. “Harder!” I bit harder. Soon her hips rose up to meet mind and I could feel my cockhead hitting the back of her pussy. “I’m going to cum soon, fill me up!” I was going to cum soon too, and began sharp jabbing motions with my cock. She was making raspy noises and she hooked her feet on the back of my thighs and kept me deep. I gushed deep into her canal, probably directly through her cervix. Her breathing quickly resumed to normal, and her feet fell to the bed. “Thanks, I really needed that.” She looked at her watch. “I wish I had time to do it again. I feel so much better.”
“You can’t stay a while longer?”
“I wish. I have to be at work at three o’clock. You may be quite a stud, but you can’t recover in five minutes. I have to go shower before reporting in.”
“You can shower here.” She looked deep into my eyes and then nodded saying she appreciated the offer. As I withdrew from her I looked down at my cock and saw red. “Celeste! Did I hurt you? There’s blood….”
“It’s the last day of my period. Sorry, I didn’t tell you. I only use a light pad.”
She asked me to shower with her, and she was surprised at how quickly I recovered. And appreciated it too.
WHAT ARE FRIENDS FOR?
Aunt Cathy called me one day as I was exiting a class. “Leah called here for you. She said she has a special request.”
“What is her number; I have a four hour break.” Aunt Cathy gave the number to me and I called it.
“Hi Drew. I have a friend with me who has a special need. Do you have time today?”
“I just started a four hour break, then have a two-and-a-half hour class.”
“Come to my place right away. I’ll pay you extra.” Leah had been generous with her payments to me so I really wanted to please her. I entered her GPS coordinates into my Garmin and drove to her place. She answered the door before I rang the bell. “Maria is my neighbor across the street,” she said walking me directly up the stairs. “She’s been married almost fifteen years and she has never had an orgasm.”
We entered a guest bedroom and I saw a Hispanic woman about 35 years old sitting on the bed fully dressed. She was very pretty, slightly overweight, manicured nails, and looking nervous. “Now, Maria, I told you to undress while I went to get Drew.”
“This…may not be…a good idea. Maybe I better go.” Maria started to stand.
Leah rushed to her side. Maria, at least try. You asked why I seemed so happy lately, and you were happy to hear I was enjoying sex. At least give it a try.”
Maria looked at me, then at Leah and nodded. “But you must stay.”
“If you want me to stay then I’ll stay.” Leah began unbuttoning Maria’s blouse. Maria stood still and let her while she looked me over. Knowing she was nervous I maintained a safe distance for her. When she was down to her bra and panties Leah had Maria sit on the bed. “Don’t you think she’s pretty, Drew?” Leah asked.
“She’s very pretty.” I said it while looking into Maria’s eyes. I took two steps forward and held my hand out to her. “Maria, I’m Drew, Leah’s friend.”
She took my hand in her soft hand. “I’m really nervous. I’ve never done anything like this before.”
“That’s OK. Just try to relax and allow yourself to feel good. I’ll do my best to help you.” As I spoke to Maria I saw Leah taking her pants off, then her blouse. She had on matching purple underwear; Maria’s were plain white. “Maria, what do you like?”
“I don’t really know. My husband doesn’t really do anything except please himself.”
“Does he do oral sex for you?”
“No, never.” Leah crawled onto the bed as Maria replied.
“Marie, get ready to have your world rocked. Drew is great at eating pussy.” I was surprised to hear an upper-society lady talk like I heard soldiers talk, but all of a sudden Maria seemed interested. Leah pushed Maria to lay down, then she pulled her panties off of her. I looked to see a very hairy pussy, probably the hairiest I’d ever seen.” I quickly stripped to just my briefs and knelt between Maria’s thighs. “If I do anything you don’t like let me know.” Maria nodded. I lowered my head and licked around her clit for several second. At first she didn’t respond, then I heard a gentle purring. Her legs spread open a little more as I began licking from her opening to her clit. I could see her stomach quivering every few seconds. I used my fingers to sort out her hair so I was unencumbered, then inserted my middle finger. I gently lubed it in her juices and began probing for her G spot. I knewI found it when her ass lifted off the bed six inches and she inhaled sharply.
“See what I mean, Maria?” I glanced up and saw Leah gently rubbing Maria’s tit. How had I missed the bra coming off? I locked my lips on Maria’s clit, inserted a second finger, and drove Maria to her first ever orgasm, and it was mind-blowing. She rocked her pelvis, gripped me with her thighs, gushed a cup of fluid, and shrieked loud enough to wake the neighborhood. When her thighs released me and I looked up I couldn’t believe the size of her nipples – the biggest I had ever seen. Her tits were large, probably a D cup, but still the nipples stood out.
“Did that please you?” I asked.
Maria swallowed hard and nodded her head. “I’m glad I stayed.”
“And the best is yet to come. He hasn’t been inside you yet.”
Maria looked at Leah, “I just need a moment to catch my breath. “
Leah went to get us all some bottled water and we chatted briefly. We were startled by the ringing of Leah’s doorbell, only to have Leah find it was the UPS man making a delivery. When Leah returned to the guest room she looked at Maria and asked, “Are you ready, Sweetie?” Maria looked at me and nodded.
I moved up next to Maria and took her nipple between my lips while massaging her clit. She soon reached into my briefs (how could I forget to take them off?) and grabbed my cock. Leah got off the bed and removed them for me, whispering in my ear “I don’t think she’s afraid of it now.” I moved two fingers into Maria’s pussy, thumbed her clit, and sent her into another orgasm. As she calmed I removed my fingers and moved between her thighs. “I need to know where you want me to cum?”
“I’m…I’m safe. I have an IUD.”
I inserted myself slowly and built to a slow but strong rhythm. Looking into Maria’s eyes I smiled, somehow communicating this was for her. She wrapped her legs around mine and began thrusting her pussy up in time with me, and her breathing deepened and sounded raspy.
“Isn’t he good? What did I tell you?” Leah coached.
Maria pulled my head down to her breast and I took a nipple and nibbled. I felt Maria’s juices soaking my balls and knew she was close, as was I. “I feel it cuming, I’m going to cum” she sang. She planted her feet on the bed and thrust harder onto me. As she tilted her head from side to side, arched her back, and screamed I rammed home and pumped my thick load into her. She collapsed and held me tight to her. I felt the bed moving and heard another shriek. I looked over at Leah to see her fingering herself to a small climax.
When I got home Aunt Cathy asked me what Leah’s special request was. This was unusual as she seldom asked me about my…clients. When I told her she said I ought to switch majors…but we couldn’t think of what to for my line of…work.
A NIGHT TO REMEMBER
Aunt Cathy turned on my light startling me awake. “Drew, it’s Celeste on the phone. She said it’s an emergency.” Emergency sex? I looked at the clock, it was almost two in the morning.
I took the phone. “Drew, I’ve been in a shooting. I need someone to come get me at the back entrance of the St Joseph’s Hospital?”
“Are you OK?” I asked. Aunt Cathy had been on her way out of my room and turned. I motioned her to stay.
“Yeah, I’m OK. But I shot a guy. Not sure he’s going to make it. Lt Harrison told me to go ahead and leave through the back exit. Security is going to let me out. There’s news cameras out front. I need a ride, though.” I explained to Aunt Cathy and she said she’d drive. We loaded into Aunt Cathy’s Lexus and made it to the hospital in fifteen minutes. We watched two people in security jackets and hats walk out with flashlights shining like they were doing a security check, but walking towards us. We knew one was Celeste. She got on the floor in the back and we quietly took her to Aunt Cathy’s.
“My partner and I pulled over a car we knew had been delivering crack. I got out of the passenger side. As I did, the passenger jumped out and started shooting at me with a .380. I ducked behind my door. I heard his rounds hit the door. I shot back twice. He ducked behind his door and I shot through it and hit him in the stomach. His buddy tried to pull a gun on my partner but it got hung up in his pants. Shit, and Lt Harrison said I was too aggressive.”
When we got back to the house I was thankful I didn’t have classes today. Aunt Cathy made Celeste a cup of herbal tea. As she picked it up her hands began shaking. Aunt Cathy took the cup from her and said, “Honey, let’s get you into some pajamas and let me message your neck and shoulders to relax you. Do you want to sit in the hot tub?”
“No, not the hot tub, but the neck rub sounds great.”
“I hope I have pajama’s that fit. I’m a little bigger than you are.”
“You’re a hell of a lot bigger in the boob area,” Celeste responded. Maybe she was returning to normal.
They returned to the kitchen with Celeste in a nightgown. Aunt Cathy gave her a neck, temples, and shoulders a good massage. “How is that feeling,” she asked.
“Really good. If only Drew would eat me while you’re doing that.” I almost spit my Pepsi out.
“I don’t think so,” Aunt Cathy laughed. “I don’t have Jim here to take care of me.” I knew she really wanted to keep our private lives, really my private ‘affairs’ private, and Celeste, though she had been joking, knew it too. Half-an-hour later Celeste was able to drink her tea. “You two do…whatever. I have clients in the morning so I need to get some sleep.” As she said this Celeste’s phone buzzed. She looked at it and told us the man she shot was out of surgery and it looked like he was going to make it.
Eventually Celeste and I went to my bed. She told me she just wanted to be held, and we were able to drift off to sleep. We woke around nine, and I had a hard-on. “Is that a ‘I have to pee’ woody, or ‘I want to fuck the chick I’m with’ woody?”
I rolled away from her and stood. “It’s both.”
“OK, go do the first, then we’ll work on the second.”
When I returned from the bathroom, still hard, she was still on her side facing away from me, but the nightgown and panties were laying on top of the bed. I removed my undershirt and short and crawled in next to her. She turned her head and faced me. “I don’t have much cash on me, I’ll have to owe you.”
I put my finger over her lips. “I’m not with a client, I’m with a friend.”
“I don’t want a pity fuck, Drew.”
“It’s not. It’s a ‘I’m glad my friend wasn’t hurt’ lovemaking.”
“Oh. Then do me.” She gave me a kiss as she reached between us and guided my cock to her pussy where she rubbed the head up and down to gather moisture. She put it to her entrance and pushed back as I pushed forward. I like spoon-position because it required a slow movement, and with Celeste’s small stature I could put my lower arm under her head and grab her breasts. Her head resting on my arm made her feel safe. All of a sudden I thought back to our last time together and how she had been, then thought of when it was. I stopped moving. “What’s wrong?” she asked.
“Think about the last time you were here. About two weeks ago. You were ending your period.”
“Shit! I’m probably fertile.” She moved her hand to my hip as if to hold me still, which I already was. I wasn’t ready for “daddyhood.” She turned her head to look at me. “I’ve been thinking of having you do my ass. Now is the time, I guess.”
“I’ll have to find some lube.” I went to Aunt Cathy’s room and got some hand lotion. I lubed her ass and put first one finger, and a second in her. She loosened fairly quickly. Then I lubed my cock and scooted behind her again. She put her top leg over me and lined my dick up with her anus.
“Go slow. Nothing has ever been in there before.”
“This is my first time too.” She surprised me by taking the initiative and scooting her ass back. My head popped in easier than I thought it would.
She gasped and held my hip steady. “I was expecting it, but not that quickly,” she hissed.
“Are you OK?”
“Yeah,” she replied. It hurts just a little, but also feels good. And I feel full.” She slid down some more and I soon had half my cock in her butt. “Start going in and out.” I began a slow in-out and she’d slide further down on me as I moved in. Sooner than we expected I was all the way in. “Hold still a moment, I want to get used to it.” I held steady, feeling her grip and release me. “OK, give it to me slowly.”
“Think you can cum this way?” I asked?
“Oh yeah, this feels better than I expected.” She took her hand from my hip and began rubbing her clit. I held her hip as I began making love to her butt. After a couple minutes she said, “I’m going to cum.”
The pressure from her ass was much more intense than in her pussy, and I was rapidly approaching climax. “I’m going to come soon too.”
She started thrusting her hips back and rubbing her clit harder as she said, “I’m almost there, cum with me!” I pinched her nipple harder as I thrust up into her and gave her a thick heavy load.” She started shrieking and put her face in the pillow to muffle her scream. After we calmed down she took her top leg off of me and turned her head. “That was great. That was better than I ever thought.”
“I liked it too.”
Celeste’s cell phone rang. I reached back, still plugged into her ass, picked up the phone and handed it to her. When she finished the conversation she told me. “Well, the perp is probably going to live. They had to remove half his lower intestine, so he’s going to have to use a colostomy bag. His days of delivering crack are probably over.”
We hopped in the shower, but didn’t fuck in there since her butt was sore. I took her to her condo to change clothes, and then took her to the police station where her car was. A few months later Celeste left the police department and became a federal agent, but I want to respect her privacy and not say which one. We continued to have sex until she left for her training, and still exchange e-mails.
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<a href="http://www.lushstories.com/stories/anal/aunt-cathys-gigolo-ii.aspx">Aunt Cathy's Gigolo II</a>