This is the story of an experienced loving man training an inexperienced woman about the joys of anal sex. If anal intercourse is not your thing, please move on. If you like the story, and you think I did a descent job, I welcome all comments and positive ratings. Thanks, and enjoy.
Hi there, my name is Zack, and my lady’s name is Zoe. We were both 32 when this story happened. Zoe was an incredibly sexy woman at 5’6” and weighing in at 120 to 125 pounds. She had long auburn hair, hazel eyes, luscious lips, perky nose, and a smile that just lit up my world when we met. Her shape was the perfect hour glass with a beautiful set of 36 C’s with nipples that were so sensitive I could get her to cum just from sucking them sometimes. Her tummy was flat and toned. Her ass and legs were what most men dreamed of having in their bed. I was very much a leg and ass man then, and I still am. The beautiful womanhood between her legs was always kept smooth, and her pussy lips opened to reveal a clit that just called to be sucked on and a vagina that needed cock on a constant basis.
Me, I was 6 foot tall weighing in at 180. I had a hard physical job that kept me in excellent shape without having to work out. My body had just the right amount of hair to make Zoe happy, and I always kept my 8 inch long, thick cock and balls shaved smooth. I loved it so when she would lick my smooth balls and suck them in her mouth to roll them around with her tongue. We both loved the way I could eat her pussy and really get her going before my dick slid inside her wet pink pussy. She was multi orgasmic as well as a squirter. I had tasted my fair share of ladies before Zoe, but I have to tell you that this woman had the sweetest juices in the whole fucking world. I just could not swallow enough of her squirting.
Our sex life together was off the charts incredible. We either fucked or made love just about every day. There was a difference too. When we fucked it was raw and powerful, almost animalistic, and those days tended to be quickies that exhausted both of us. When we made love it was passionate and tender how we would slowly take each other, and spend all the time needed to fully satisfy the other. There was not a room or piece of solid furniture or counter top she had not been fucked on in our home. Both of us had voracious sexual appetites, and extremely high sex drives. Neither of us was shy about asking for whatever we wanted from the other, and we both always listened to and tried to please the other with anything new one of us wanted to try.
Early in our relationship, we had been together for several years now, I had asked Zoe if she was interested in getting fucked in her sexy ass. I promised her that it would be a gentle and loving experience for her, and that I would train her and guarantee a wonderful pain free new experience. You see when I was a submissive in my early 20’s, my Dom had me train several college ladies to become her anal sluts. I had experience with this, and frankly I never had a failure to take my dick easily when I was done with any of the 6 women I had trained.
Zoe said, “no she was not interested at that time, but maybe someday in the future that would change.” She promised to let me know if it ever did.
Zoe shared the story how when she was in college her boyfriend had pestered her so much that she finally gave in to make him stop. It was not a pleasant experience for her. In fact it had been extremely painful. She told me how the boyfriend had a good 7 inch cock that was kind of thick. He had not taken any time to even try to prepare her tight virgin ass. He just lubed her up and rammed his dick balls deep up her ass. She said the pain was immediate and intense, and that she even bled for a day. She jumped out of bed so fast and kicked him out of her life for good after hurting her like that.
Back to the present day now, and we were lying in bed cuddling after just fucking each other’s brains out one night, she told me she was now interested in the idea of exploring anal sex with me. She said she thought I was just the right man for this, and that she trusted me to be gentle even though I was much bigger than the old college boyfriend. She wanted me to assure her that it would be enjoyable for her. Needless to say this caught my attention immediately. I had to ask her though, what had caused her to change her mind?
Zoe told me that she had been talking with Amy who was with Gus now for the last year. Early in their relationship, Gus had trained Amy to receive anal penetration. This man had been extremely gentle and loving, and had taught Amy how to do it so that it was enjoyable and even orgasmic. Amy shared some wonderful stories of their passionate anal love making with Zoe, and this was peaking her interest now. Zoe said, if I could make anal that kind of gentle, loving and passionate an experience for her, then she would like to give it a try with me.
Seizing the opportunity I said, “hell yes I would do that, but that we would not be able to just try. If you want me to train you anally, you have to commit to learning and doing, not trying.”
Zoe told me that she was still hesitant, but that she trusted me. She said she would commit to doing the training and fucking her ass at least once. If she did not like it, then it would be a onetime only thing. I agreed with her. If she did not like it after the training and our first time, we would never go there again.
After that agreement, I started to talk to her about doing proper anal training. How we would use toys and butt plugs to get her used to being penetrated in her ass. She looked at me questioningly, wondering how I knew this much about it. Without her even having to ask, I told her the story of the dominant cougar I had been fucking in college who loved getting fucked in the ass. The cougar had told me what she had done and gone through to get her ass stretched out, and what she had done to condition her mind. That old woman was so stretched out that she even liked having her ass fisted. The cougar told me how being the anal bottom was not just a position, it was a mind set. If the bottom thought it would hurt, it would because they would tighten up. Tightening up is what makes it hurt I told Zoe. After the dom taught me how to train a new bottom, I trained 6 other women anally. All of them were successful in that training and enjoyed taking my big dick every time the Dom cougar had me fuck them.
For the next couple hours I explained everything I would do with her to get her stretched out and ready. That it would be a process, not just an event. We talked about how her mind had to be right for this to work. How she would have to will herself to loosen up instead of tightening up as she was penetrated. It was explained how we would start small and work up in size. In the evenings during training she would keep a butt plug in all evening, so she got used to things being in her ass. I taught her about cleaning out inside, just like she kept her pussy clean. She would need to do the same thing with her ass before getting fucked.
The next day I went by the local sex shop, and bought all the toys and equipment needed for Zoe’s anal training. This was going to be fun for both of us. It had been my desire to train that cute little ass since the day we met. I brought home good lube, 3 dildos starting from a slim Jim model to one a little bigger than my dick. When she could take that one for several days straight, she would be ready. There was also a set of 3 butt plugs. The last thing I bought was an enema kit for her to flush out with. I knew this would be work for both of us, but it would be well worth it in the end.
Zoe was diligent and sincere in her training with my help and guidance. We had a lot of fun with it as she got used to her ass being penetrated. Everything I did with her, I was gentle and loving showing my concern for her pleasure. Turned out she loved getting my dick in her pussy when she had a plug in her ass. She let on that maybe we would have to find another man to join us sometime, so she could have a DP. The idea certainly turned me the fuck on. I wondered in Amy and Gus would be into that idea? After two weeks of good training, I knew she was ready, and she knew she was ready too. After opening up with the big butt plug, she was having no problems comfortably take the large dildo. We made plans for that Saturday night; she would get fucked in the ass by me for the first time.
We decided to go out for an early dinner. We were going to taking our time and enjoying this new experience for her when we got back. . I wanted to make this one of the most sensual and passionate experiences she would ever have.
When it was time to get ready, I gave her privacy to flush out and prepare her ass for tonight, and then we showered together. We washed each other in the most wonderful ways. We had a large square shower with two shower heads, and I made her stand leaning her hands on the wall, and her legs spread. In her spread position, it was easy to reach around and soap up the front of her body. Rubbing across her slippery soapy nipples always got her going, and I so enjoyed running my hands down that flat tummy and down her thighs to come right back up to her pussy. While I was doing that, my body was tight up to her ass with my cock between her legs. Reaching down with one hand from the wall she rubbed her pussy with my cock. The head of my dick split her lips and I could feel her clit hitting my cock as she twitched. Leaning full forward and away from me, she backed up and impaled her pussy on my cock. I loved in when she got aggressive like that. I was standing still as she bounced on my cock trying to get me to cum. I had to save it for her ass later though. As she bounced on my hard cock I just watched her work it, A low muttering stream of fuck fuck fuck fuck, was emanating from her. Her legs were starting to shake as she got closer and closer till she gave me her final push back so hard it almost knocked me over. Fuck yesssss, she screamed as she came all over me. After she came I just held her hips back tight on my cock as I felt the muscles in her snatch contract on my cock. I gave her a moment to settle down. We turned off the water, dried off and headed for the bedroom.
Going into the bedroom to get dressed, I told Zoe I wanted her biggest butt plug in her ass while we went out to dinner. With her devilish smile, she got on her knees doggie style on the edge of the bed with her ass in the air for me, and just said, “yes sir, I am ready for you to slide that sweet plug up my ass Zack.”
There she was with her pretty little clean rose bud wide open for my taking. My cock would be there before too long I kept reminding myself, but rimming her a bit would not violate the plan for the evening. Dropping to my knees behind her as my cock stiffened again, I gently kissed both of her sweet round ass cheeks repeatedly. This was a first for her. The feel of my lips on her ass cheeks was most pleasurable. She had her head and shoulders flat down on the bed and her legs spread wide for me. Everything between her legs was exposed to me. Giving her a surprise, I licked her from the bottom of her mound, splitting her pretty pink pussy lips open as my tongue hit her clit, and I tasted her hot juices. Slowly but surely I went right up through the crack of her ass. She moaned when I crossed her clit, but she squealed much loader with surprise and joy when my tongue centered back in on her tight little asshole. I worked my tongue around the edges of her whole as she moaned and wiggled. This was something I had always wanted to do with her, opening her world to the joys of anal sex.
“Oh fuck baby that is good,” she cried as I pushed my tongue into her hole.
After a few minutes of eating her ass, I stood up with my cock so hard it almost hurt. I wanted to take her right then and there, but that was not the plan. Doing this too early, without proper loving preparation for my big dick would hurt her. I was not going to allow that to happen. Instead I kept to the plan and lubed her ass and the plug, slowly inserted it taking special care to reminder her to loosen up. She had been a bit tight, but relaxed as soon as I reminded her and took my other hand and started rubbing her back. The plug slid in completely, so I slid it in and out a few times to get her loose.
She started to moan. “Baby I want your dick in my ass real soon,” she told me.
“All in due time,” I reminded her as now my other hand moved down to her pussy. She was so wet.
Rubbing her clit and fucking her with the butt plug, I could tell she was building already. My dick was so hard. I needed to fuck my lady’s pussy, and I needed to fuck her right now. Stepping behind her, I ran the head of my dick up and down the lips of her pussy. She cooed her approval as I slid my cock balls deep in her warm wet pussy and filled her with my cock. Buried in her for a moment, I fucked her with the plug some with my cock in her. I could feel the plug’s movement on my dick. It made we wonder what it would be like when we had another man with us to fuck her in the ass while I fucked her pussy. Quickly though, I came back to the reality of the moment. She was putty in my hands. Sliding the plug in fully, I grabbed her hips and started thrusting my cock in and out of her pussy.
“Yes baby yes, that’s it fuck me,” she cried. She liked being fucked slowly. She wanted to feel every movement, and I was just the man to give her exactly what she wanted. Her hand went to her clit as the head of my cock was hitting her Gspot. She was building quickly, and in just a few moments went over the edge, her body shaking and her pussy squeezing down on my cock as she squirted all over.
Pushing me back before I came, and pulling herself off my cock, she turned over and laid on her back on the bed with her head hanging over the edge. We had a pretty high bed, so the angle was pretty good for what she wanted. She wanted me to face fuck her and drive my hard cock deep down her throat like we had so many times before. I knew my lady, and I knew how to give her what she wanted.
“Give me my appetizer you fucking stud,” she told me before she reached up to grab my hips and pull my dick into her mouth. I was so close when she came while I was fucking her just now, that it did not take long as I slid my throbbing cock in and out of her mouth and throat. She loved my cock when it was coated in her juices. I could feel it building again quickly. My Zoe loved to have me cum in her mouth. She loved to swallow every drop of my cum every chance she got. As I quickly went over the edge she just held the head of my dick in her mouth and closed her lips around my now pulsing cock filling her mouth with my cum. She knew my cock got painfully sensitive right as I came, so she just held it there. I pumped one, then two, and finally 4 jets of cum in her mouth before it stopped. MMMMM she hummed and swallowed immediately.
Then she looked up at me with those bedroom eyes. “Next one better go in my ass mister,” she warned me. I just smiled and nodded, yes.
Cleaning up just a bit and getting dressed we headed out to get back and continue after I recovered for the main event in a few hours. Her butt plug was still firmly in place.
The dinner was nice. We enjoyed each other’s company, shared a bottle of wine. The whole time I kept thinking how once we got home, my cock would be balls deep up her ass where that plug was right now. It was clear in her eyes that she was thinking the same thing as she looked at me. When we got home, we headed straight for the bedroom.
In the time it took me to light the candles and turn the background music on, she turned down the bed, and was already naked on the it. I commented, “You certainly are rather eager this evening.”
She replied, “shut the fuck up, and strip mister, get this plug out of my ass and fuck my ass.”
I stripped quickly and climbed up on the bed in front of her spread legs. She was so beautiful and sexy laying there like that. She wanted fucked, she wanted fucked by me, and she wanted fucked in the ass tonight.
She asked me, “what position do you want to fuck my ass in first?”
I already had my plan. I told her, “just like this lover, face to face. I want to look you right in the eyes as I slide my hard cock up your ass.”
“ MMMMM that sounds wonderful” she said.
I took one of the pillows and folded it in half, told her to lift her ass, and put it under her sexy butt. “That’s perfect babe,” I told her. I wanted to get her going though, and tease her a bit more, so I swung around and straddled her in a 69. As soon as I did that, she had my cock in her mouth. Gawd she was such a slut, but she was all mine. Spreading her legs wide apart, I went straight to work on her pussy. Using my tongue, I spread her pink lips open to lick her clit and started to work the plug in and out of her ass a bit before I threw it over on the floor. Her ass was nice and ready now. As I eat her pussy, I knew she was ready, but I wanted to get her off once before I fucked her ass.
Dipping three fingers in the lube I had set up, I slid them up her ass as I eat her pussy. My fingers slid right in. All I had given her till now was toys and plugs. This was the first time she had any part of me up that tight little ass. She moaned with my cock in her mouth as I eat her. The vibrations felt amazing as she built up. As she started getting close she always let go of my cock from her mouth. That was my sign that I needed to pick up the pace with my tongue and mouth. A few more licks on her clit, and I went to full out sucking on it and tonguing it at the same time. That did it, her whole body tensed, she squirted right in my face, and her ass tightened around my fingers. As her body collapsed from her first orgasm, I moved my arms under her spread legs and got my hands under her ass. Lifting her ass up higher, I moved my tongue to her rose bud. She took my cock back in her mouth and moaned again as I teased her hole with my tongue, but the time had come.
Swinging off of her and moving between her legs, I lubed her ass and my cock. “Are you ready for this babe,” I asked.
“Fucking ah right I am ready son, now make love to me and go for it,” She said.
Just to be sure I clarified, “you want my hard cock deep in your ass now babe?”
Looking me in the eye she said, “yes my dear, I want you to fuck me in the ass face to face so I can see the look on your face as you slid in me this first time.”
Moving in closer on my knees, I pushed her legs back to her chest. Instinctively she held her legs back and curled her hips up to give me full access to her open ass. Lubing her ass and my cock, I moved in closer. I had been waiting for this for years. I had done the best I could to prepare her for this, and she was ready now. I knew she was going to enjoy this as much as I would.
Putting the head of my dick to her ass, I looked her in the eyes and said, “relax Zoe, relax as deeply as you can. Let your ass open up and let my dick inside you. You have to let me in, I will not force my way in and hurt you.” As my cock first pushed a little I could tell she was nervous and tightening up some. “Relax Zoe, you are ready, you know how to do this.” As I rubbed the backs of her legs I felt her asshole start to relax, so I pushed in a bit more. The head of my cock was starting to make entrance into her ass as I watched her hole going in and spreading open. As I looked down at my dick for a moment, I could see the head was starting to go in as her hole was spreading open to let me in. “That’s it relax Zoe, you are doing really well,” I told her. She closed her eyes and exhaled, she was pushing back on me like I had taught her with the toys. As she pushed just like when she had to go, she relaxed completely, and the head of my cock popped into her ass without me having to force it in. I stopped right there as her eyes opened wide and she looked into mine.
“Fuck babe, we did it. You are inside me now, and it feels fucking great. Let me have some more hon,” she said. She was ready so I pushed in to about half way and stopped again. I felt her tighten just a little, so I rubbed her legs and coached, relax again. As I rubbed her legs I pushed my cock in her ass the rest of the way.
“Gawd that is such an amazing feel. Your cock is all the way in my ass,” she said.
Looking her in the eyes, “yes, you have all 8 inches in you now Zoe, how are you doing,” I asked.
“Fucking great babe, this is amazing, no pain, all pleasure. My ass just feels full in a great way, and it is all your cock giving me this great feeling,” she said. I left my cock parked in her as I let her adjust for a moment, and I leaned in to kiss her. Our lips met, and I held her legs back with my arms as we kissed. It was genuine; I could feel it in her kiss. The training had worked very well. She had just taken 8 inches of my thick cock balls deep in her ass that two weeks ago could not take a finger without hurting, and now she did not hurt at all.
As we kissed I slowly pulled my cock out an inch or two and slowly pushed back in. I wanted to let her feel every movement gently inside her. So far so good so I kept moving slowly like that as we kissed. “How you doing Zoe,” I asked her as I continued to slowly fuck her just a couple inches.
“It’s fucking great babe. Nothing like the first time, and your cock is even bigger than his was. This is amazing babe, I love it,” she said. “You are being so sweet and gentle, what a difference.”
Taking this as a clear green light that she was enjoying getting fucked in the ass, I kept the same slow speed, but started giving her longer strokes. We kept kissing as she got her ass fucked. She told me she never thought it would be this good. That she had been nervous about the training, but that I had been so gentle and kind that she learned to trust me even more than she already did. She saw that it really was as good as I said it would be for her. Here she was now with my dick sliding in and out of her ass, her arms wrapped around me as we kissed passionately and made love, only it was her ass getting fucked not her pussy. It was not humiliating or degrading to her in any way. It was passionate and loving. Pretty soon I was giving her good full strokes, pulling back till the head of my dick almost came out, and then slowly sliding back in balls deep and parking for a moment. We got a nice gentle rhythm going at a pace she was just deeply enjoying.
Her ass felt fucking amazing and so snug around me as she took my dick. Her pussy was sweet and felt good, but her ass was just right tight and it made every nerve in my dick stand on edge even more. I was getting close now, but I did not want to come yet. Leaning back, I pulled out completely, picked her ass up and started eating her ass again for a bit of a break to let my dick settle down. As I curled her up like that her hole was gapping open from the size of my dick. My tongue went in deeper than ever before. She moaned and wiggled as I eat her.
After settling down a bit, I relubed my dick, set her ass back down, lined up and slid right in balls deep. This will be a little different now Zoe, tell me what you think. Slowly I pulled out completely, and then gently pushed right back in balls deep. I did that several times and she loved it.
“Fuck me doggie now babe,” she said to me.
“Sure Zoe, get on your knees,” I said. She threw the pillow aside and was right on her knees. She had a wide stance with her head down that gave me that great view of her pussy and her now gapping ass. Lining my cock up, I moved in and drove in all the way again, stopped and let her adjust.
“Fuck that feels even better. It feels deeper and fuller. I think you can start to really fuck me now babe’ she said. Did not need to tell me twice, picking up the pace some, but still being gentle, I let my cock slide in and out of her sexy ass. Noticing her hands were not visible, I saw she was starting to play with her pussy as I fucked her ass. She played with her pussy with one hand and grabbed my balls to keep me in close with the other. She was hot right now. I could tell she was starting to build.
Keeping a steady pace and watching my cock going in and out of her, I noticed she gave off the oh so familiar signs as she started to tense up. Her hips started to buck, her hand was flying fast and furious on her clit, she was holding her breath, and bam, it hit. The spasms of her orgasm racked her body. Her ass tightened down on my cock so it was almost impossible to keep it in. She was bearing down trying to push me out as she came. I just buried my cock in as deep as I could go till I felt her relax and start coming down. Gently I started thrusting again.
“How was that Zoe,” I asked.
“That was the most intense orgasm I have ever had. I had no idea anal could be so good, fuck babe, what I was missing all these years. I should have let you train me years ago,” she said.
“Things always happen at the time they are meant to happen. This is your time, and you are here now, that is all that matters Zoe,” I said.
“New position Zoe”, I said as I pulled out. “Put a pillow under your hips, and put your hands on your pussy and lay flat on the pillow on the bed.” She did just as I said. Spreading her legs open, I put my right leg outside of the V of her legs. Gently I covered her, and my hard slick cock was back in her like this. I kept up a gentle but steady pace. She was mellow now, and as she played with her pussy, I could tell she was edging. Since I kept my pace nice and slow we were able to just keep going for a good while. Once I was tired of holding myself up like this, it was time for another position. This next position she would get my load in her ass.
Pulling out again for a moment, I positioned her on her left side with her knees curled up. Getting on my left side behind her I slid right back in. So I could hold her tight as I came. My left arm was slid up under her pillow, and my right arm was around her body holding her left tit. She laced the fingers of her left hand into the fingers of mine. Her right hand was between her legs. Gently, I started to cuddle fuck her just like that. Keeping the pace gentle, I knew I could go a long time like this, but I did not want to wear her out on the first time. She cooed as she played with her pussy and I thrust my dick in and out of her open ass.
Speaking gently into her ear, I asked “do you want to cum inside you now?”
She said no. She was very happy with this gentle anal cuddle fuck I was giving her, and that she just wanted me to keep going like this for a while longer. She was so comfortable and relaxed like this. I kept it going nice and gentle for her for a good 30 minutes.
“Zoe, I can’t hold back any longer,” I told her.
Turning her head back towards me, she said, “then breed my ass and fill me with your cum lover.” This was it now, I pulled my arm out from under her pillow, pulled my other arm from her body and moved back so I could have my hands on her shoulders as I drove my dick and my load deep in her ass. Picking up my pace to a full porn start jack hammer, as hard and fast as I could, it was clear she was ready. Her ass felt so good on my cock as I went from gentle to faster to full pounding strokes.
“Fuck yes, yes, yes,” she said, as her hands flew on her pussy. She was getting pounded just like a porn start in the movies now, and she was ready for it, loving it, and actually feeling and enjoying it.
Her body started to shake, and she was holding her breath again as her hands bore down on that pussy. It was stars and fireworks in the room as she went over, and her ass clamped down on my dick trying to push me out again. It was my turn now though. My dick was super hard and flying in and out till then as I held my breath to go over. As she clamped her ass down on my cock as she came, that pushed me over the edge too. I buried my hard dick balls deep in her ass. As she finished cumming, my cock began to erupt. With my cock parked so she could feel every squirt of my cum and pulse of my cock in her ass. She felt the 5 full jets of cum squirt in her bowels. She was sated and happy.
We both laid there spent for the moment with my dick still in her. Gently but firmly I slid my arm under her pillow and wrapped my other arm around her body and pulled back into spoon cuddle her with her ass full of my cum and cock. We pulled the sheets up over us and just snuggled in the afterglow.
A bit later Zoe told me “thank you love, that was fucking amazing and so much better than I ever dreamed. I thought letting a guy fuck my ass would be pain I had to endure it to make him happy. That was never going to happen to my ass again. You showed me it is immense pleasure instead. With your gentle, kind, and loving nature I should have known better. You did not just fuck me, you made made passionate love to me. That was simply amazing my love.”
“You are most welcome Zoe, and thank you for giving me the honor to train you and show you what an ass fuck can really be like. I had to wait till you were ready and interested, I am glad you and Amy had been talking,” I told her.
“Zack,” she said, “we will be doing this a lot more often. Any time you see that flush out kit out, know you will be fucking my ass that night.” She pulled my arm in tight to her belly and squeezed her ass on my softening cock. We fell asleep just like that, cuddled with my cock in her ass. It was all I would do with her ass that night. She had been fucked for over an hour that first time. That would be enough anal for tonight.
Around two in the morning I woke up still in her, and gently pulled out to go take a shower. Never take a cock from her ass and put it in her pussy without washing unless you want to give her an infection that can kill her. After my shower, I came back to bed and snuggled back into here and slid my dick up her pussy. Her ass had received a proper work out. The rest of the night was for her pussy now.