Loading...This is my first submission. It is a chapter from a much longer story I’m working on. It is essentially a true story, with names and events modified to ensure the privacy of those involved. It is very detailed, a story of unrequited love and missed opportunity, romantic and tender but also intense it its anal themes. It’s the story of my brief time with Catherine, a woman I fell in love with and think of often.
Catherine…when I was in sales I would always be assigned the new, inexperienced customer service reps; I had a record of being an excellent trainer, would coach them into being the best in the office, and then they would be reassigned to some other sales rep who was barely competent and needed a highly competent customer service rep to keep his business together. Every one was young, female, attractive and too often, very interested in bagging a six figure sales rep or up and coming young manager—many did. I appreciated the complement from my boss, but was often frustrated at always having to be in training mode.
Catherine came on board right out of college; over educated for the job and very bright, she had interviewed for a management, entry-level job, wasn’t seen as quite up to the task and agreed to take an hourly job; it was conveniently located to her home and there was the promise of a reevaluation down the road. Since she was bright and had a first class education from a top name university, she learned astoundingly quickly and became a superb customer service rep.
I never fooled around with the office staff; they were all gossips, it would have been bad for morale and most were little more than shop girls. Cat was different. My first marriage was also on its last legs; my ex and I were separated, divorce was imminent and I probably shared more of my frustration with Cat, who was not a shop girl, than I should have. We would banter very non-sexually on the phone, she was the classic girl next door, and I grew to have a genuine affection for her. I’d see her in the office several times a week and occasionally take her on the road to meet our customers. She was around five six, with small breasts and an athletic body from college soccer and cheerleading. Her phone voice was fantastic and all of our customers loved her. She had dirty blond hair and a cute, if not beautiful face. She never came on to me or me to her. I respected her immensely and the respect was mutual.
I had met her parents and had no question in my mind that she was a nice girl. The guy who finally married her was a young, good looking guy in the sales force. He fell head over heels in love with her; he once told me that she wouldn’t let him get in her pants until they were married. I went to her wedding; her family was prominent locally and it was a huge and lavish affair. I was protective of her when it came to the other guys in the sales force and never hit on her.
One day I was in the office to go over some problems involving service to a particularly difficult customer. Cat and I went into a small conference room to discuss the issues with the Ops manager. That meeting took about 30 minutes; the Ops manager left and Cat and I talked for a few more minutes and then she asked me if I played tennis. I told her yes, but badly. She said the condo she had recently moved into, her first after moving out of her parents’ home, had great courts, but nobody seemed to ever use them. Cat was an early riser, as were most of my more demanding customers, so she was very happy coming in at 6:00 AM and working until 2:00 PM, which perfectly matched my schedule and that of my key customers. Cat asked if I’d like to play tennis with her some time. I said sure, and reminded her that a couple of days a week I was actually calling on customers not far from where she lived…like today, for example. Her face lit up, and she smiled broadly, and for the first time since I had started working with her, got that hint of a come hither look on her face, almost seductive as I looked back later, but I really missed the signals that morning.
I told her I always had my tennis stuff in the car with me and she said I could change at her place. We decided to meet at around 3:00 PM and she gave me exact directions. I swear I didn’t have a sexual thought in my mind.
I got to her condo at the appointed time, changed from business attire in her bedroom, admired her very tastefully decorated home and noticed that, in tennis togs, her firm, athletic body was very attractively displayed. The weather was hot. We played a vigorous tennis round for about and hour. I must admit that watching this coordinated young lady work her end of the court was very arousing. After an hour we were both ready to call it a day. She made a great shot to end the match and bounded over to give me a big hug, which was much less platonic than I would have expected. Back at the condo, she told me I could have the shower first, so I closed the bedroom door, stripped and jumped in the shower.
Within a couple of minutes I was totally shocked when she opened the door and stepped in, stark naked in all of her young beauty. She held her finger to her lips as if to say, ‘don’t say a word’, and began to lovingly wash my back…and my ass and my cock. Wordlessly, I returned the favor, lathering up her tits, cunt and ass. I got down on my knees and ate her pussy…she came in a matter of seconds. She went down on her haunches and blew me to orgasm in less than a minute. We kissed, groped and fondled. We washed each others hair; my dick was hard again.
“Wait for me in the bedroom.” She whispered. She came out of the bathroom a few minutes later and gave me one of those incredible post orgasm, sloppy wet and warm kisses.
“I’ve had a crush on you since the first day we worked together. There’s one small problem. I’m a virgin. I intend to stay that way until my wedding night. Call me old fashioned. I really need some comfort right now, and with everything going on in your life, I know you do too. I want to make love with you. But I can’t let you in my pussy…that’s reserved. If you wouldn’t be too grossed out, I want to give you my ass. If not, I won’t be offended. I’ve taken it in the butt before and enjoy it, and I took the required steps to ensure that my ass is clean and well lubricated. Have you ever…ah, done it that way before?”
I told her that I had some extensive experience in that department and would be far from grossed out. I began to finger her ass hole. It was very well lubed. I told her to roll over on her front and began to softly rim and then more vigorously tongue fuck her delightful little brown eye, while carefully fingering her clit.
She came, and rolled over. “Take my ass from the front, I’d rather do it that way.” She cooed.
I agreed. She got a bottle of Astro-Glide from the bed table, lovingly lubed my cock, She smiled and softly urged me into action. “I need it now baby, please fuck me.”
She held her muscular legs back against her small, firm tits; I got on my knees and inserted the head of my cock into her ass.
“I haven’t done this is quite a while, so let me get used to it.” She whispered.
It took a few minutes for her to adjust, but finally she said, “I’m ready now, do me.”
I started a slow stroke, taking her hand and placing it on her pussy so she could help get herself over the edge. We got into a rhythm and I increased the pace. I stopped moving and whispered in her ear. “Fuck me Cat, fuck my cock with your ass.”
She proceeded to thrust her ass up off the mattress, rotating and moving her butt, literally screwing my cock with her ass. “I’m not going to be able to hold out much longer in your hot, tight little ass hole.” I said.
“Just another minute, I’m so close.” She groaned.
Her moans increased in frequency, she began to pant, like a women giving birth, her eyes closed, her head rolled back and she came, long hard and with a series of soft, but audible screams. The contractions of her orgasm on her anal canal took me over the edge and I dumped a fresh load of hot cum deep in her rectum. My dick plopped out of her ass and we cuddled and kissed and fondled. She got out of bed, returning a few minutes later with a warm rag and two glasses of red wine. She cleaned my cock, and my ass, playfully inserting s well lubed finger up my butt and then took the now soft member in her mouth and playfully rolled it around with her tongue. I knew I could go again, but would need half and hour or so to recover. We drank our wine, virtually wordlessly and she snuggled up next to me.
“I think we both need a little nap time.” Cat suggested.
We fell asleep for over half an hour, when I awoke, I had rolled over with my ass facing her and she was proceeding to rim my butt hole. She got something from the bed table, which I quickly discovered was a small vibrating butt plug, lubed it up and began inserting it in my anal canal. “Tell me if this hurts, or you just don’t like it, and I’ll stop.” She cooed, as she proceeded to carefully insert the plug in my ass with one hand while using her other to lift my cock so she could lick the underside. The combination of her oral attention and the butt intrusion had me once again, hard as a bone.
She then pushed the entire plug in my ass, and asked, “Can you hold it in there?”
I told her I thought I could accommodate her. She then reached back in the drawer of treats next to the bed a produced a vibrating egg, which she proceeded to insert in her mouth and lavish with spit, then incredibly erotically inserted the egg into her pussy, so that all that was showing was the battery pack wire, lewdly hanging from her labia. I realized that I had a similar wire trailing away from the end of the butt plug she had shoved up my ass. Rather than getting up on her knees, she turned her ass toward me and rocked back on her haunches, leaning forward on her forearms so that her anal passage was perfectly aligned to be violated, her butt cheeks obscenely spread for my inspection. She handed me the control for the egg in her pussy and deftly picked up the control for my butt plug.
“You won’t have to take it easy this time, that cock of yours opened me up nicely. I kind of prefer an on and off action with the electronics, low level at first, building to a constant high level when I get close. I know how I like it, and would normally take control of my tool myself, but as good as that last ass fuck was, I have confidence that you know your way around a woman well enough to handle the task, plus the surprise of not knowing what’s coming from the egg can be really hot. Do you trust me to hit the right buttons on the vibrator I just shoved in your rectum?”
“Absolutely, I trust you implicitly.” I said, almost in shock at how my nice little girl next door took control of her own sexual pleasure—and mine.
“You’re good and hard and have already cum twice, so I’m anticipating and am hoping for a long and very satisfying ass fuck. You lasted the first time longer than any man who has ever been in my ass, a very pleasant surprise, particularly since you’d never had my ass before. Most guys cum in seconds in any woman’s butt, but it’s even worse the first time. You’ve obviously done your share of ass fucking and that experience is very much appreciated. I’m very ready for you baby.” She said as she reached back and inserted two fingers into her anus.
“When a girl has decided to save her cunt for her wedding night, good ass fucking becomes a mandate; you’re certainly not the first, but you’re the best I’ve ever had; make me your little anal slut.” Cat was very matter of fact at this point.
With no further conversation, I slowly inserted all nine inches up Cat’s sweet little rectum.
“I really am a nice girl. I’ve really only let a handful of guys take my ass, and most never really got the hang of it. When I’ve got a man’s cock in my ass, particularly a man who knows what he’s doing, I do get nasty. I like to talk dirty. A little butt slapping wouldn’t hurt either. This is whore fucking. You can treat me like your own personal little anal whore. Tell me how bad and nasty I am to have seduced my, ‘boss’ and to be letting him fuck my hot little butt twice in a little over an hour. I want to be your dirty little girl. I want you to stretch my anal ring like it has never been stretched before. Tell me that only a depraved, wanton little slut would let a man do this to her, and enjoy it. Make me your own personal anal fuck slut. Take that ass hard. Show me no mercy. Pull my hair, jerk my head back. Pinch my nipples until I scream. Don’t make love to me this time, just ball me. I may be the nice girl at the office, but right now you’re balls deep in my dirty hole. I’m just a nasty little cunt you picked up who gives up her ass for free. I need a man’s cock in my ass…I’ve got to have it.”
I got into the role play and responded accordingly. “You are a nasty, dirty little bitch. You’re such a little whore, and an ass whore at that.” And I slapped her ass and began seriously driving my cock into her precious, firm little ass, balls deep on every stroke.
“You like being my anal bitch, don’t you, Catherine? Need to be man’s cum slut. You give up your ass so easily; you like to be stretched, need to hurt.” And I yanked her hair back and forced my tongue into her mouth, biting her lip and pinching her tit until she cried out.
Meanwhile, somehow we both had the presence to work the remote controls on our respective toys, and the vibration through her cunt wall combined with the vibrator up my ass made my cock even harder but actually seemed to forestall cumming. I think that is exactly what Cat had in mind. After a while, and I’m no clock watcher when I’m getting a hot young woman’s ass, I rolled her over on her side; she held one leg up without having to use her arms, a testament to he superb physical conditioning.
“Look at it Cat. You can see my cock stretching your anus, it’s obscene. You’ve got three fingers in your cunt, you’re really a dirty little girl. Where’s my cock, bitch?”
“Deep in my ass.” She answered. “I love a cock in my ass. I had a dream, you are the man in the dream, following me back from the tennis court, forcing me to suck him off, threatening to rape me. I beg him—you, please not my pussy, but you can have my ass. He ties me spread eagle on the bed, face down. He gets on top of me, spits on my ass hole, twists my head viciously to the side and forces his cock into my mouth to get it wet, then plunges it in to the hilt into my, ‘virgin’ ass. I scream in agony, beg him to stop, but he is relentless, pounding my tight little ass hole for what seems like hours. Dumping his load deep in my rectum. Forcing me to clean his cock with my little mouth. Tying me in different positions so he can violate me from every angle. Fucking me almost hourly all night until I give in and start to like it…and he knows he owns me. You own me. You own my ass hole.”
It had to be the most intense and nastiest, but somehow oddly romantic ass fuck I’ve ever had. And after we both came and removed the appliances, we lovingly fell asleep in each others arms. Over the next couple of months, Cat and I played tennis at least once a week, and engaged in wanton butt fucking, until I introduced her to the man she would marry, a young sales rep who wanted to ask her out. I was always protective of her, and almost acting like a father, told him that if his intentions weren’t honorable, to back off. He was fucking a string of girls at the time, but understood that Cat was a cut above his usual fare.
Right before he proposed he told me that he was not going to get any pussy until they were married, which I already knew. She’d suck his dick and he’d eat her pussy, but that was it—and he’d never gotten a shot at that experienced little butt. During the courtship, Cat and I stopped playing tennis and stopped our anal exploits.
They got married in a beautiful wedding; nine months later she gave birth to a beautiful little girl. I actually double dated with her and her new hubby a number of times when my divorce was final, but I have to say it was difficult to look in her eyes because it would bring back such erotic memories.
When she was about six months pregnant, she called me one day to come over for dinner, but said, don’t bring a date, just dinner with old friends. When I got to their house, her husband was not there, which I should have known. He was on the other side of the state on business. She looked good, glowing as pregnant women do, obviously pregnant, but very sexy in her condition. She cooked a delicious dinner, and we moved to the living room to enjoy a brandy.
“How’s your sex life?” She boldly inquired.
“Oh, I’m getting laid on a regular basis, but no one I want to spend any time with, and a bunch I don’t ever want to see again. I kept the little house I bought to live in during the divorce; it was 100% VA financed, so I figured I’d use it as a rental property, but lately I’ve been using it as a place to take dates that I may never want to see again. ‘Kept my old Toyota; ‘don’t really want them to know where I live or how much money I have; some of them are almost stalkers. I’ve had to go unlisted on the home phone and change it a couple of times. ” I told her.
“Did you and your ex fuck when she was pregnant?” She asked.
“Yes, right up until the day she delivered, she was incredibly horny when she was pregnant. Mostly just straight fucking. She had a little problem with varicose veins during her pregnancy, never really got into ass fucking until several years later. But I’ve always found pregnant women very sexy.” I responded, wondering where this was going.
“Well, I’ve got a problem. I’ve never let Terry have my butt…remember he married a, ‘nice’ girl, and I’ll let him one day, but not now. We’ve lightly touched on the subject, but I’m not sure he’s even into it. Remember, anal sex is something I enjoy a great deal, an important part of my sexual awakening. It will take time to bring him around, but that’s going to be a few years down the line. My doctor— what an asshole—doesn’t really want us to have sex from here on out. Now Terry’s a damned good little muff diver, and I keep him happy with daily BJ’s, butt I desperately need my ass hole drilled. I can’t move a lot, and with this belly, it’s not easy to get in a comfortable position, but I was hoping you could help a damsel in distress; are you up for it?”
” For you Cat, anything.” I replied.
We proceed to the bedroom, she struggled out of her clothes and began to move some pillows around.
“This is really embarrassing. I’m not comfortable on my back, too much pressure from the baby. I’m going to have to situate these pillows, get on my knees, might have to move to my side, present my ass to you and ask you to do 90% of the work. After the baby comes, I’ll make it up to you. This probably won’t be too exciting for you, but I really need it.” She explained.
I undressed, she got into position, and I began to work her bung hole with my tongue and lips. “Already lubed, Cat; you knew damned well I couldn’t say no? Didn’t you?”
She replied. “I knew the first time you took my ass that you were as bad an anal freak as I was, so I highly doubted that you would disappoint me.”
It was a very gentle and loving ass fuck. She was so sexy in her pregnant state. She still knew how to work her anal muscles to grab and release my cock. It was such a pleasant surprise because I assumed I’d never enjoy her anal expertise after her wedding day. No dirty talk, but probably more loving exchanges than a guy should be having while he is anally fucking a good friend’s pregnant wife while that friend is out town.
“Could you have fallen in love with me?” She asked.
“I’ve always been in love with you.” I replied. “My life was such a wreck when we got together. My divorce was messy and I wasn’t remotely ready for a real relationship for at least a year. I’m 14 years older than you. I’m sure you folks would have loved it if you’d fallen in love with a guy who is almost 40 and has two kids and an ex wife.”
“I knew all of that. “She said, as I continued to slowly and lovingly stroke my cock in and out of her butt.
“I knew that you and I would never go that route. But I dreamed about it; I so wanted you to be the first man in my pussy; I so wish this baby in my belly could have been yours. Hell, I even married a guy that a lot of people think looks like a younger version of you. And he’s a very caring and loving husband. You’ll always be the love of my life. When your divorce was final, and Terry and I were planning our wedding, I came so close to knocking on your door one night, hoping you weren’t getting laid at that moment and literally asking you if you would even consider marrying me, and if you said yes, giving you my pussy on the spot. What would you have done?”
“Cat, I was an emotional wreck. My life had lacked intimacy for too long. The girls I was fucking meant nothing, just plumbing. I would have said yes. I would have married you in a heart beat and given you all the babies you wanted. But I would have been a shitty husband. I was lonely and detached, completely unable to get involved in a loving relationship. It would have been so unfair to you, and if I’d jumped into a marriage, even with you, who I’ve been in love with for so long, it would have been a disaster for both of us. I needed to get healthy, and that takes time.”
She sobbed. “Life can be so unfair. I love Terry and he’s madly in love with me, but too many times when he is fucking me I see your face. We need to stop this talk, it’s not good for either of us. Make me cum lover; my ass will always be there for you, and even my pussy. I love the way you feel. I love your touch, oh, God, make me cum!”
I softly shed tears which I knew she could feel on her back. I felt her old familiar moves as she got close to going over the edge. At the height of her orgasm I came in her rectum. We cuddled, and kissed. We got dressed and returned to the living room and chatted some more, as if there had never been that intensely emotional anal interlude. We never fucked again; she would have, but I couldn’t. I couldn’t deal with the power she had over me or the power I had over her. I knew if I ever took her pussy I’d want her forever and if I asked her to leave Terry and marry me she probably would have, which would have been awful for everyone involved, particularly the children.
We never double dated again. I saw her after her second daughter was born; I was picking Terry up so we could work together. We shared a platonic hug and acted as if I was nothing more than a work friend of her husband and she the young wife of a guy I worked with.