The Saga Begins ... The year I turned 24 was a major turning point in my life. I was two years from a nasty divorce from my first wife and was just getting my confidence back as regards to dating and relationships. I had just started a new job and was making more money than I had up to that point in my life. Not only had things begun to look up financially, I had somehow stumbled into the most exciting period in my sex life. The people that I met during this time of my life would feed on my new-found confidence and bring me some of the most exciting sexual encounters I could ever ask for. I had married young, at the age of 17 I met my first wife while still in high school and despite the fact that we began to have sex at a young age, soon after we met, the only saving grace to our sex life was the fact that I was able to go all night, and therefore provide her with all she needed through frequency and probably not quality. I say this because after our divorce I learned how to pleasure a woman and be pleasured by a woman in ways I never imagined I could or would enjoy. This all came about because of a job I took immediately following my divorce. I truly feel that this job and my subsequent sexual education lead to every bit of the wild sexual times I have had in the last ten years. I will tell this story and if it is well received I will write about the crazy places it took me. I was working my way through college after a stint in the military and without my ex-wife’s income I needed a little more money and took a job working for an engineering firm. My new boss was Sandy, and my responsibilities included helping her with the many computer related tasks that she had little aptitude for. Despite being an architect and highly educated she often had trouble with the most basic drafting and other computer related tasks. This meant that I was often in her office working over her shoulder or her over mine as I fixed whatever mind boggling error she had made. Working in close proximity with her was making a very sexually frustrated man out of me and thank God for what happened next. Sandy was 39 when I met her and was about 5 years from a divorce of her own. She was raising an eight year old boy and sharing a house with her 35 year old sister. She had an unbelievable figure, one that I would often catch the youngest of men around the office checking out, and long blonde hair, just past shoulder length, and the most beautiful face. She wore only a minimum of makeup and didn’t need even that. She dressed in clothes that both accented her figure and gave her a younger look, not that I considered her old by any means, but our age difference would be what brought us together and eventually what tore us apart After working with Sandy for about a month we were becoming fast friends and had begun to take a liking to each other that went far beyond work. One Friday during work Sandy asked me if I would like to go to a movie with her and her sister. I wasn’t dating anyone and was glad to have the female companionship. That evening we went to the movie and I met Sandy and her sister Becky at the theater and my whole world changed. Becky was just as beautiful as her sister and was more or less a younger carbon copy, with shorter brownish-blonde hair. We had a great time at the movie and when it was over went for some dinner. During the movie my hand had brushed up against Sandy a few times and she would look over at me and smile giving me a good feeling about our budding relationship. I had ridden to the restaurant with the women and left my car at the theater. We had dinner while talking and I flirted with both women paying most of my attention to Sandy but getting the feeling that Becky was interested in me as well. I knew that I couldn’t have both of them, neither of them had ever given me the indication that they were into that and I decided that I had better put most of my effort into winning Sandy. Soon the check came and ever the gentleman I paid and we left the restaurant. Sandy drove us directly to her house and I never thought anything about the fact that I had no way of getting home, I was at her mercy and I realized later she had it planned that way. We continued to drink, the two women and myself, them drinking wine and I with my beer. After about an hour of conversation and drinking we were all a little buzzed when Becky brought the conversation around to relationships, sex, etc. and I recounted some of the details of my marriage, blaming the fact that I was a backward redneck hillbilly for my divorce and not that my wife was a two-timing bitch. I told them about my subsequent rebound dating and lack of anything meaningful since. Becky then proclaimed that she had it worse than me, four years she had spent “perfecting the art of self-love. I was a little shocked but I rolled with it asking Sandy if she had been loving herself any lately, and she rolled her eyes. We laughed and Becky excused herself and said she was going to bed. She lived in the basement of a large spit level home, the two sisters owned together. Sandy had excused herself from the room at the same time as her sister and I sat back down on the couch wondering if I had missed my cue to leave, and in just a moment I received my answer. Sandy returned to the living room having changed into a sexy set of pajamas consisting of a cotton t-shirt and a pair of short tight cotton shorts. The pink shirt had the words “good night” in bright red and thoughts ran through my head as to what that might involve, a good night with this incredible woman could be amazing. “I just got this new back massager” she said as she sat down beside me on the couch and handed me a small massager about the size of my hand, one end was slightly pointed. I was actually dumb enough not to take the hint she was giving me. Sandy stood back up and said "I’m sorry I forgot about your divorce, I know what it’s like to be hurt. It leaves you confused and kills your self confidence. Well, this is going to be whatever you want it to be, casual, meaningful, whatever you want it to be.” I looked into her eyes and kissed her for the first time and without a word we walked into the bedroom. It had been so long (six months) since I had been with a woman. I was just enjoying the intimacy and soon Sandy was taking the lead again. She broke our kiss just long enough to remove both of our shirts. I immediately went to work on her magnificent breasts. She had large puffy nipples with small pink areolas, sitting on top of titties a 20 year-old woman would die to have. I sucked and nibbled on her nipples eliciting moan after moan from my new lover. After a few minutes of this I hooked my thumbs into the waistband of her shorts and slid them down over her slender hips, revealing a hot pink thong. I resumed kissing her momentarily until she unhooked my belt and forced my pants down. I removed my socks as we crawled into the high bed and lay next to each other our legs entwined, my thigh rubbing against her panty covered slit. Again I got a little caught up in the moment, lingering a little long, however Sandy took charge rolling me onto my back as I relinquished my grip on her left breast. On her knees now she pulled up on the waistband of my boxers taking a peak inside then looking up at me and smiling. A smile I was glad to see. I had always faced problems with women due to my size, not too little, but way too much for many women. Size doesn’t matter in the least when it comes to pleasing a woman. That is when the size of your cock is not way too small or way too big. Mine was way too big, porn star big and many women found this a real turn off. Sandy however was not one of those women. I was about to learn that when some women see that you have more length, or width for that matter, than they have ever taken it creates an air of excitement in the bedroom. This is in no way meant as bragging, as you will see in my next story, it just is what it is. Sandy moved back up to me and kissed me deeply, then moved down kissing me around the chest and on my nipples working her way back down to my boxers grabbing them and working them down, never taking her hungry eyes off of my cock. Just as soon as my boxers hit the floor her hand was pumping my cock up and down. She quickly took the head in her mouth, just enough to get it wet enough so her hand would slide up and down my shaft, soon my precum was helping her lube my shaft as she started to lick my sack very gently. She moved between my legs and I spread them to accommodate her. The next thing she did I never thought I would feel, and certainly never thought I would enjoy feeling. Her hand was stroking faster up and down my long thick cock as her tongue started to wander down my sack and very close to my asshole, despite the surprise and unusual feeling my pleasure was reaching heights I had previously not known. At this point my mind was telling me not to come, but my body was reaching what I thought would be an orgasmic plateau, however my pleasure kept rising as she gently let the tip of her tongue work my asshole. I was feeling my orgasm building but these wild new sensations were overloading my system and I was experiencing such intense pleasure throughout my whole body. My breathing was slow and shallow as she pumped my shaft faster. I was lost in amazing waves of pleasure and then I felt two amazing sensations that sent me into a convulsive orgasm. Sandy’s head rose from between my legs just as a wild new feeling lifted me over the top. Sandy brought her mouth up to my cock and sunk face down on it farther, deeper, than any woman had ever done to that point, just as she inserted her long skinny finger into my ass and curled it forward to massage my prostate. As if she had pushed a button I had the most intense feeling rush from my balls to my head and spread out throughout my body to the farthest reaches of my fingers and toes. I unloaded waves of cum into the back of Sandy’s throat and mouth. Like the amazing sexual minx that she was she swallowed every drop and gently eased her finger from my ass. I finally regained my breathing just as Sandy was slowly finishing her reward for several minutes of very intense work. I could feel her swallow one last time as my cock spasmed again and slipped from her beautiful lips, which were now forming into a gorgeous smile and then a little laugh as she looked deep into my eyes and crawled up to lay on my chest. Her head was turned to the side as she lay with her head over my heart that was now returning to a normal rhythm. “Please don’t think of me as a total whore just because I was so starved. It’s been two years since I’ve had sex” She said obviously embarrassed. “I hope you don’t think of me as a sexual novice, that’s the most intense sexual experience I’ve ever had. I have to admit, I may not be as sexually educated as I should be, size is my biggest asset” I told her, adding “I have always been able to recover quickly though, sometimes fucking three or more times a night.” “Well you never know if you don’t try” she replied. “I hope I can get you where you need to go, my wife wasn’t much for oral sex, giving or receiving.” We were now kissing again, she was still lying on top of me and I rolled her off of me and onto her back squeezing her titties and pinching at her nipples as she panted between kisses. I removed my tongue from her mouth and began to suck her tit while helping her remove that amazing pink thong. I think I actually gasped at the sight of her very hairy pussy. She had very light brownish-blonde pubic hair covering her pussy, but due to its light color her pink prominent lips peaked out enough to excite me to a point that I could feel my dick come back to life. As the thong hit the floor my hand slid over the thick yet neatly trimmed hair of Sandy’s bush. She was quite wet and my finger easily slid between her slick labia. I let my middle finger slide along her labia and clit a couple of times before gently penetrating that beautiful pussy with a single finger. She was just dripping with thick slick lubricant, as my finger slid in and out of her pussy she moaned just loud enough for me to barely hear her as I sucked and nibbled on her nipple. At her gentle urging I released her nipple from my mouth and moved my body down between her legs. Sandy moved up the bed a little to allow me to lie on the bed with my face over her pretty little pussy. I began to kiss and gently lick her pussy taking in the taste and smell of my new lover. As I would gently cross her clit with my tongue she would moan ever so slightly. I decided to attempt to please her in the way she had, moments before, so thoroughly pleased and surprised me. I would focus for a couple of seconds on her clit then let my tongue slide down across her opening to her asshole and back up, just grazing ever so slightly her pink anal bud. The volume of her moans increased from low to medium and back down as I moved back and forth. Using her physical and auditory cues as encouragement I started using my tongue exclusively on her ass bud momentarily and she gave me the right reactions as she raised her ass off the bed forcing it into my tongue and saying my name out loud repeatedly. After less than a minute of working her asshole with my tongue she said “finger my ass and go back to my clit” between heavy breaths. I immediately sunk my finger into her pretty little ass and quickly started stroking her clit with my tongue. Her moans became urgent and I started stroking my finger in and out of her tight little ass. She had continued saying my name in a quick cadence over and over. I stroked and licked as she moaned and chanted my name. I realized that she was quickening her pace and breathing shallow as my excitement rose along with hers and for whatever reason I let my first finger slide into her pussy so she had a finger sliding in and out of both holes as I worked her clit with my tongue. Both of us were now working together as I stroked her G-spot with an urgency. I saw her hands go to her tits and squeeze them while pinching and pulling her nipples just as she screamed my name and yelled “God, your making me cum.” I continued to stroke with my fingers but applied gentle pressure with my tongue to help reinforce her pleasure. I had never made a woman cum through oral sex before this and felt both proud and a little ashamed that I had never been that thoughtful of a lover. Without her prompting I never would have been able to get her there and her example gave me new places to stimulate that I would never have thought to go. By the time she caught her breath I was laying beside this beautiful new lover of mine. We kissed passionately and I rubbed my hand along her thin tight body enjoying alternately the feel of her skin, soft over her breasts, tight over her abs and down to her slippery pink lips. My cock was now as hard as it had ever been and was getting some attention from Sandy once again. She had her hand wrapped around my long cock and was just barely jerking me off as we kissed. I started to maneuver myself on top of her but she soon pushed me back onto my back. “I’ll need to work this in slowly, I’ve never had that much before and sex just shouldn’t hurt” a notion she would later change her mind about. “Don’t trust me yet?” I replied. “It’s just that I don’t quite trust you to control your need for pleasure, this will be good for you too.” She smiled as she said it, shaking her head to get the hair out of her face. She swung her leg over and straddled me, my cock coming to rest between her dripping wet labia. She began by sliding back and forth along my cock coating it with her thick juices, slicking me up for the penetration I was hurting for. She then rose up onto her knees and reached down to grab my cock and position it at her entrance. As if she were being penetrated for the very first time she slid only fractions of an inch down before retreating and then advancing. Soon she was working the first three or four inches in and out of her pussy, as she would go down the large butterfly lips of her pussy would momentarily disappear and then reappear as she slid up sliding along my cock and providing me intense pleasure as she attempted to take all of me. She was looking deep into my eyes as she did this and slowly she gained ground on my length. Now she had over six inches inside of her as the look on her face morphed into surprise and a bit of discomfort. She dropped her head to view my cock slipping away into her pussy. I was having the most intense pleasure of the night and she was determined to keep me at the height of ecstasy despite her discomfort and I could see more of my cock had entered her but she was really struggling to get down on it now. “I feel like its prom night all over again” she said clearly having trouble. “It took my ex-wife two months to take it all, but she was a virgin” I laughed “but you shouldn’t hurt yourself, I’m in ecstasy with just a few inches inside of you.” “I can’t describe it, it’s not pain it’s just a different kind of stretch, painful pleasure” she smiled and went back to work. “Just go slow” I whispered. She continued in and out for several more minutes heightening my pleasure and soon she was sitting on my pelvis with all of it deep inside her sexy body. She lay down on my chest and we kissed and let our hands roam all over each other. I would just slightly move my hips from time to time to increase my pleasure. After ten or more minutes I rolled us over and onto her back. The only thing she said was “easy” and took a deep breath. During the maneuver I slid out of her two or three inches and now slid back in slowly and she finally moaned in pleasure again. I reached over on the bed and grabbed the ‘back massager’ and turned it on. Sandy smiled from ear to ear. “Do you want your back massaged?” I asked. She snatched it out of my hand, turning it to the medium setting and responding “my front” placing it over her clit. She wrapped her legs around me and I started slowly sliding my long thick cock out of her pussy. I looked down and saw her inner lips hugging my cock as it slid out of her pussy. When several inches had been exposed she pulled me back in with her ankles. I sensed she had reached a comfort level and started picking up my pace just a little, but quicker nonetheless. She started moaning and she was trying to find a cadence again when she said “God your cock is so amazing, I feel like I’m stretched as far as I could ever be, don’t you get carried away and hurt me.” I just smiled as my cock pistoned into and out of her body giving me intense pleasure as she lubed my cock with more of her thick juices. We had worked ourselves into a frenzy again and her cadence was quickening as she chanted in time "fuck, fuck, fuck, fuck” repeatedly. I took the vibrator from her keeping it in place over her clit but letting her hand go to her tits where she began to knead them and pinch at her nipples. I pulled my cock from her pussy and rolled her to her stomach grabbing her by the hips and helping her to her knees. I sensed she might like this as I could get at her sensitive asshole. I let my cock come up between her lips and gave it a couple of bounces so my cock bumped up into her clit as she moaned “put it back in baby.” I grabbed her ass cheeks and spread them apart so I could see her pussy and let the head come into contact with her lips. I could feel how wet she was as my head penetrated her hole, sliding in much easier this time. I went slowly so as not to decrease the pleasure she was feeling now. I easily slid in about half way and started to push in and out using just that much to get her going again after that short break. I placed the vibe up against her pink anal bud, between us the vibe tickled and stimulated her ass and provided some extra stimulation to my cock, not that it needed it. My cock was now on fire, in an indescribable state of pleasure, like the first time you actually get to enjoy sex, after you figure out what your doing, and you first get to just stroke you cock in and out of a soft wet pussy, pure ecstasy. Now Sandy was starting to get a cadence again like a train leaving the station her cadence was picking up “fuuccck … fuucck … fucck ... fuck … fuck, fuck, fuck, fuck.” At this point I started to feel and sense some urgency. My cock was begging for me to bury it so I told Sandy “I’ve got to go deep.” “I’m o.k.” she gasped panting. I started in rapidly going from three or four inches to my entire length buried deep inside that beautiful pink pussy. Now I stroked my cock in and out of her in long strokes. My head would just appear between her labia and then slide all of the way to the hilt, as my balls slapped forward. At the end of each stroke a high pitched scream would escape her lips. Soon she was forcing her ass backward and our hips would slam together. She would increase the speed then slow down until finally she developed a good rhythm, our bodies slamming together at the end of each stroke. I knew she was rounding the corner and heading for home. I took the vibrator from between us, licking a finger and curling it into her ass. “Oh yeah, hit me harder” she cried. I worked my finger in and out a few times then removed it and grabbed her slim hips with both of my big hands and ran for home. I would let my cock slide almost out of her and then pull her hips backward and let our bodies slam together, our pace picking up and her moans getting urgent. I felt her hand go to her clit and start to rub as my orgasm started to rise. She yelled “God I’m gonna cum so fucking hard.” I had to hold her up by the hips to keep her from collapsing as I slid in and out of her. Just as she came back to earth I started to cum and shoved forward while spreading her ass apart with my hands hitting someplace deep inside of her I had yet to reach as the cum started to gush, squirt after squirt into her tight little pussy. My cum was being forced out around my cock as I held her hips pressed against me with all the force I could as my cock spasmed and flexed inside of her body. As my orgasm subsided I started to relax my death grip on her hips and we both collapsed forward with our genitals still locked together. I lay on top of her my face buried in her hair panting and trying to catch my breath. She was the first to speak “I never thought of pain as a precursor to pleasure, but taking that cock was the most pain my pussy had felt in years” she laughed and continued “as I stretched though the pleasure over took me.” “I’ve had the opposite happen as well” I replied. “Ahh little girls shying away from that monster, poor thing” she laughed, mock sympathy. “In high school one girl refused and two others made me stop before I got in more than an inch or two. Do you know how frustrating that is for a young guy, horny as hell and you have to stop before you even get started?” I reasoned. “Well it’s paying off now ain’t it” she laughed and turned her head so I could kiss her cheek. I got to my knees straddling her pelvis and still buried deep inside her. I slid my length from her sloppy wet pussy with an audible slurp. Cum drained out on the bed spread as I got off of her. She rolled over and stood up beside the bed cupping her hand under her pussy. “I am so stretched my pussy will never be the same” she looked concerned as she said it. I smiled and replied “hopefully it won’t have to be.” “Well you can always hope, there’s no law against that” She said, disappearing into the bathroom and ending a fabulous lovemaking session. This lead to an unbelievable time in my life that in many ways is still going on. I would like to continue to tell the great folks out there about the many exciting sexual encounters that this gave me the confidence to have so let me know if you enjoyed this story through your votes.