Little Oral Andy

"Twenty-seven, actually," I answered.

I'm not sure which one of us blushed more.

She was a helluva fuck although her pussy was definitely loose. I could see by her face she was embarrassed by that, and she quickly explained that she had torn when she had the first of her four children 26 years ago. I pulled out, pushed her legs practically back on top of her and pushed back inside, in effect tightening her pussy and making things better for both of us. She groaned her approval when I pushed back in, then started to moan uncontrollably as I pumped her harder and faster. She screamed through her first orgasm five minutes later, and she came twice more before I finally emptied my balls inside of her.

Considering how much fun I always had with Auntie Nipples, I didn't have a problem with Jenny being almost twice my age, and she didn't seem to have a problem either. We went out twice more and had a great time both nights, so I thought it a little odd when she turned me down for a date on a Wednesday, the first time I had asked her out on a weekday. She put me off and told me she would be available on Friday. Okay, maybe biological researchers had some late nights, too.

A month later Jenny and I had a late Friday night of fun. As usual, she was very responsive to my oral ministrations, coming six times before I crawled up her body, put her feet on my shoulders and started to pound. She came twice more before I came, then we both drifted off to sleep. We woke some time after 8, with me spooned around her. I was about to initiate some morning play when she look at the clock on my bedside table and practically went into panic mode.

"Oh shit, I'm going to be late!" she practically screamed at me. "Why did you let me sleep so long?"

"You never told me to leave an early wake-up call, princess," I snarked back at her.

I waited a week before I asked Jenny out again. I waited until we were served dessert before broaching the subject of what was happening in her life that she was trying to keep secret. Tears welled up in her eyes.

"It's never going to end, Andy," she said sadly. "I threw away a great marriage just to have some sex with another man, which turned into several other men over a period of a year. I went from having a great life to being a 51-year-old single mother of a 3-year-old. I went from being a respectable professional to a cock-craving slut and now I have to worry about a precious little boy. I should have been straight with you from the get-go, Andy."

Jenny's little boy was indeed precious. We enjoyed several outings with him, but we both knew that a long-term relationship wasn't in the cards.

A few months later I got a call from Auntie Nipples, saying she needed a favor. How could I turn down my favorite aunt with the boobs of a goddess and a sweet-tasting pussy? Well, it turns out the favor was for a friend... a smart, sexy, curvy friend, one who got a hose job from an ex-husband.

Katelynn Sweeney needed a boyfriend -- not just an escort -- for the wedding of her oldest daughter in a couple of months. The wedding weekend was three days in Boston, and Katelynn wanted to not look pathetic in front of her ex-husband, who had divorced her after 20 years of marriage to marry a 24-year-old trophy wife two years ago.

Auntie Nipples was a long-time friend and co-worker of Katelynn Sweeney, and after hearing the whole story, Auntie Nipples "volunteered" my services. It didn't hurt that Katelynn was 47 but looked 37 and was still a beautiful woman, according to the photos my aunt sent me.

My "job" then was to date Katelynn several times before the big weekend so we could build up a familiarity with each other, then to accompany her the entire weekend of the wedding. Sex was optional, at Katelynn's discretion, Auntie Nipples informed me.

One look at Katelynn in the flesh made me wish the sex was optional on my part. The woman was beautiful, and after two weekends spent with her, I thought she was beautiful on the inside as well. I had to wonder about the intelligence of her ex.

I met Katelynn's daughter, Jocelyn, on my third weekend visit. She was a little shocked that her mother was dating a much younger man, until Katelynn pointed out that Jocelynn's father had actually married a then 24-year old.

"Oh yeah, Mom. I guess what's good for the gander is good for the goose. Well, I'm glad to see you're not alone anymore," Jocelynn said.

As many of the wedding party and guests were from out of town, the Friday activities included touring historic Boston. When Katelynn came downstairs Friday morning, she was braless in a Red Sox T-shirt that was a size too small, nicely showing off her B-cup boobs and nipples, and she was wearing a tight pair of Daisy Dukes. Her long platinum hair was in a pony tail under a Red Sox baseball cap. I'm pretty sure I drooled a little when I looked at her, and I know for a fact that her ex stopped breathing for a minute. I could see that his trophy wife felt a little threatened by the look as well.

"God, Mom, you look hot!" Jocelynn gushed in front of those assembled, causing Katelynn to blush and me to smirk.

"That's my girl!" I quickly followed up, moving to her and giving her a peck on the lips.

I noticed that her ex practically snarled.

We did a couple of museums and a bistro for lunch as a group. I made sure to either be holding Katelynn's hand or have my arm around her for most of the time. I even wedged my hand into her tight back pocket for a while, causing her to smirk at me. I definitely enjoyed watching her boobs bounce and sway in her T-shirt throughout the day, and I also loved the view of her crotch in those tight shorts. She gently smacked my hand when I rubbed the inside of her upper right thigh one time.

I may not be the final judge on women, but I really had to wonder about Katelynn's ex. Trophy wife was definitely a looker, but she had nothing on Kate except she was 21 years younger. Hell, I even caught Jocelynn's intended groom taking a few surreptitious looks at his mother-in-law to be.

Katelynn and Jocelynn prepared a grilled feast at Kate's house that night after we did the rehearsal at the church. I helped out as needed since I had learned the layout of where things were in the kitchen on my visits. I was getting a little tired about 11 p.m., so I pulled Kate aside and quietly told her I was going back to my hotel.

"Oh, no, Buster, you're not going anywhere. Your aunt tells me you're the world's best pussy eater, and I intend to find out if she's correct."

"No pressure there, Babe," I said.

Everybody except Jocelynn finally left about 1 a.m. Jocelynn was staying in her old room, and I followed Kate up to her bedroom. Kate quickly adjourned to the master bath while I stripped down and got into bed. It took Kate a while, and I just assumed she was a little uncomfortable about me seeing her undressed. I was way wrong on that assumption, because a minute later she came out in a frilly white bustier, frilly white bikini panties and shear white stay up stockings, with her hair combed down to the middle of her back. Oh, my God! Amazingly to no one, probably, my earlier fatigue completely disappeared.

I got back out of bed, hard as a rock, and proceeded to run my hands all over "my girlfriend." I found her collarbones to be extremely sensitive to my touch and my tongue. When her breathing got ragged, I pulled her panties off her body, laid her down and slowly inserted one, then two, fingers in her wet pussy. She came hard twice yelling unintelligibly, then I removed the bustier and sucked on her adorable nipples for a few minutes as she writhed on the bed. She was dressed in only her stockings and heels when I put the flat of my tongue up against her pussy and she exploded in a huge orgasm, shrieking out my name as she came and soaking my face in her juices.

Thus encouraged, I placed her legs over my shoulders and went to work, sticking my tongue into her opening until I hit her G-spot. I licked up and flicked back as she went crazy, climaxing at least two more times. I then went to work on her clit as she tried to beat me senseless by ramming her pussy into my face, leaving me dazed if not confused.

I took a few minutes to catch my breath and get my wits back, then crawled up, rubbed my hard prick up and down Kate's nether lips and then slowly sunk in all the way. As she grunted and moaned, I pulled back almost all the way out, then slid all the way back in as she orgasmed again.

I spooned around her as we drifted off to sleep. I thought that I was going to have to buy Auntie Nipples a really good Christmas gift.

Lunch was catered-in heavy hors d'oeuvres at Kate's. Kate wore a short yellow sundress, once again braless, and looked hot and adorable -- if that's possible. I went back to my hotel to shower and change clothes, and when I got back the snacking was in full swing with the whole wedding party and more milling about.

"Hey, Stud! Did you need to go back to the hotel for a little nap?" Jocelynn called out when I walked in the door.

Almost at once, all heads turned in the direction of Katelynn. She blushed from her upper chest all the way to the top of her forehead. I have to admit I may have colored some, too.

I walked over to Kate and gave her a pretty good kiss on the lips. She rolled her eyes at me and I could see them glow. I grinned back at her.

Later on I saw Jasmine, the trophy wife, sidle up to Kate, and tell her that she looked absolutely radiant. Kate smiled and said I was the reason. Jasmine asked her what she had been feeding me, but I didn't hear the answer as Kate leaned close and whispered the answer in Jasmine's ear. They both turned to me and giggled.

There's almost nothing better than a beautiful woman straddling your face in bed. Kate was sitting on my chest, sort of, and I was feasting on her gushing pussy several hours after the reception was over. This woman was a goddess, and I as I was greedily licking for all I was worth, I was trying to figure out how I could get her to come to Minneapolis.

An hour later, we were lying side-by-side in her bed enjoying our afterglow when she broke the silence.

"My god, Andy, I've had an amazing weekend... in addition to my daughter getting married. Thank you for being here for me. You've been great company and kept me from looking pathetic in front of everyone... including my dickhead ex-husband. Everyone thinks I'm hot and fun.

"I've got to thank Diane for everything."

"You are hot and fun, Kate," I said. "Would you ever consider coming back with me to Minneapolis? Or making room in your heart for me here in Boston. I think you are everything I'm looking for in a woman."

She colored adorably. I watched the wheels turn in her head. For a brief moment, I thought she was going to say yes.

"If I was 10 years younger, Andy, I'd be giving you a yes. I feel the connection, both physically and emotionally, but I've been with my company for more than 20 years, and Boston has been my home my whole life. And I wouldn't feel right making you move here to be with an old lady..."

"You are definitely not an old lady..." I started to say, but she held up her hand in a gesture of stop.

"Seriously, Andy, there is a woman out there your age just waiting for you; one that you can have kids with and build a family. I had my family and a great life until that all changed, but thanks to you, now I'm confident I can find someone to spend the rest of my life with. You don't happen to have an older cousin or something out there, do you?"

We kissed and made love gently one more time before falling asleep. We did the exact same thing one more time on Sunday morning. Kate then made me a sumptuous breakfast before I drove my rental car back to the airport and grabbed my plane.

My first nephew was born about a year later. Traci and her husband of five years still lived in my old hometown, so I took some vacation and went to visit.

On my third night in town, I stopped off for a drink at a local watering hole I used to call my home away from home.

"Oh my God, Mighty Mouse!" came the yell from behind the bar.

I looked over just in time to catch Janet Sunderman as she jumped into my arms. She was wearing a tight T-shirt and short, tight jean shorts, and just out of reflex I caught her with my hands on her ass. I gave her a quick squeeze and then she put a lip lock on me that made me instantly hard. She giggled and ran her hand over my crotch.

"Mmm... been a long time since I've said hello to Mighty Mouse Jr.," she commented as I blushed.

She released me and went back behind the bar. She was the night manager and bartender. I made sure to sit at the bar so we could talk and I could ogle her.

As she moved around behind the bar, I noted that her shorts rode up on her legs a bit... and there it was: her version of the Mighty Mouse tattoo. It was as high up on her inner thigh as it could get without being above the bend in her leg and just below her pussy. She caught me trying to look.

"Do you like my tribute to the world's best pussy eater?" she giggled. "You know we all got them... in different places."

"I saw Dottie's a few years ago, right before she married what's-his-name. She visited me at school," I said.

"That little tramp," she laughed. "Did you two...?"

"I normally don't kiss and tell, but you girls were always different for me. Yeah, she was a couple of months away from popping and we... I didn't realize that pregnancy changes a woman's taste," I said.

"Does this mean that I can come visit you when I'm pregnant and you'll take care of me?" she asked, raising her eyebrows meaningfully.

"Kids yet? Who's the lucky guy?" I inquired.

"No kids, and I'm still not married..."

"Wait. What?" I interrupted. "How are you still not married? All the guys around here turn gay? Wait, you turn gay?"

"No and no. You remember Eddie Abbatiello, from back in the day? We got close, then I found out her was cheating on me. That stung real bad. I've had a few boyfriends since then, but nothing serious. And besides, I've never found anyone who can eat pussy like you... not even another woman."

She gave me a coy look, but didn't elaborate. I didn't feel it was my place to ask.

"What about you, Mighty Mouse? Surely some smart woman has latched on to you and your talented tongue by now. I haven't talked to Traci in a bit, so I really don't know."

"There's an old saying, Janet. You can make a girl cum buckets, but you can't necessarily put a ring on her finger."

"Then you haven't been going out with the right girls in Wisconsin," she said.

"Minnesota, but close enough," I said.

"Whatever," she chirped. "You ever consider bringing somebody from here back there?"

I may not be a genius, but I was smart enough to pick up on the hint.

"Do you realize that I've probably ingested gallons of your cum through the years, but we've never actually gone out on a real date? Are you free any night this week?"

Janet's tanned olive skin looked amazing in the skintight white club dress and sandals she was wearing when I picked her up two nights later for our first date. The top was open to the middle of her big boobs and the hemline barely made it down to mid-thigh. I shook my head when she answered the door.

"What? You don't like?" she asked, looking very concerned.

"No, I love. I just can't believe that you're still single."

You don't take an Italian girl to an Italian restaurant; we went to a Brazilian place and both had something spicy that I still can't pronounce. We then went to a dance club for a few drinks to let the meal settle before we hit the floor.

I'll admit I'm not a very good fast dancer, but I can hold my own on the slow dances. Janet didn't seem to mind on the fast ones, and on the slow ones she molded herself to me. That body pressed against me produced the result she seemed to want. We left the club after a while and headed back to her apartment

Her body was every bit as luscious as I remembered from several years ago, and she tasted every bit as good as I remembered. Somewhere about the time she shrieked out her fifth orgasm on my face she suddenly stopped moving and making noise, being passed out completely. I lifted my face from between her thighs and waited until she regained consciousness, then climbed up her body and put my rock hard dick into her sloppy, steamy pussy.

"Oh, Mighty Mouse..." she moaned. "God, I've missed you."

She must have been telling the truth, because I didn't leave her apartment until she had to get ready for work the next evening.

We were lying entwined in her bed after our first romp of the morning when Janet looked at me anxiously. I caught the look out of the corner of my eye. She fidgeted for another minute.

"What? Please tell me you're not really married and I just cucked someone," I said.

"No. Nothing like that," she responded while turning her eyes down. "I-I-I need to apologize to you. Actually, we probably all need to apologize to you -- the three of us -- Dottie, Maria and me. We used you. We used you for sex all those years ago. None of us cared about you; it was all about us getting off. It was pretty selfish on our part.

"I'm sorry. I feel really cheap."

She looked up at me with real tears in her eyes. I was puzzled for a few seconds. Then I just figured since we were apparently telling each other the truth, it was my turn.

"You shouldn't lose a minute of sleep over that," I answered brightly. "I knew you were using me, and I was using you three right back. Come on, Babe. I was having weekly sex with a beautiful woman who otherwise wouldn't have given me a second look.

"Traci didn't lie to me one bit. She told me that her birthday gift to me would change my life, and it has; not only because I got to have sex with her hot friends, but with my confidence in real life. I honestly don't think there's a woman I date that I can't please, and that kind of confidence translates into many other areas of my life.

"And don't discount the fact that I'm addicted to eating pussy."

She laughed uproariously.

"God, I've felt guilty about that for all these years since you left."

"Okay, so how is a decent-looking guy with your skills still on the market?" she asked.

"Because I learned early on the difference between sex and love. I have had sex with my share of women, but I have yet to find the one to love. And when I do find that one to love, she will be the only one I'll ever have sex with again. I guess I'm old-fashioned that way."

"Wow. How come we never talked like real adults before, Mighty Mouse?" she asked.

"Because you were too busy using me as a human dildo, just a mere sex toy," I responded, "and I was Traci's little brother. You women never took me seriously."

"Our loss then," she noted.

"How about we leave the past in the past and work on the present now?" I asked. "Let's drop the Mighty Mouse thing. Try Andy, from now on."

I extended my stay two days and Janet and I spent the time together when she wasn't working. Several times I caught her looking at me strangely and shaking her head.

"Damn, Mi... Andy, you were right in front of me for years and I never even knew it," she said while we were lying in bed together the night before I was to fly back.

We tried a long distance relationship but it didn't work. I needed to have my hands and lips on her lux body, not seeing her on my phone or my computer. I convinced her to join me in Minneapolis, which saved me on hand lotion and her on toys. After six months of living together, I asked her to marry me, and she accepted.

"But you need to know something first, Andy," she said quietly after first shrieking out her positive answer.

I know I visibly cringed. I had gotten close before, only to be disappointed.