8 comments/ 160720 views/ 14 favorites Stepmother Ch. 01 By: SpeedoLight THEN: The soft Side. My stepmother and I had maintained a peculiar relationship, ever since she had had caught me trying to sneak one of my fathers girlie magazines back into his bedside cabinet; one that I had torn out a few pages from. At the time I was 18 and had just come home from boarding school for the summer holidays. I have to admit I had always had fantasies of being dominated by a woman, not a cruel woman mind, but rather one who would enjoy playing a fantasy role as dominatrix while I indulged my pleasure in being dominated. In my stepmother I had found such a person. She had covered for me with my dad, by disposing of the magazine in question and saying that she had found a particularly tasteless article that had offended her so much she had consigned the magazine to the garbage bin. Luckily dad did not question her further about it. I had never felt such humiliation in my life as I had upon her catching me, in her and my dad's bedroom, going through his bedside table with a girlie magazine in hand! She had been really nice about it, after her initial disgust at the intrusion to their privacy, understanding that I had had little in the way of mature sex education, nor had I experienced my sexuality being confined to an all boys Catholic boarding school. Anyway the upshot was that she would not show the magazine to my dad or tell him about my episode, but I would have to allow her to train me and bring out the repressed sexuality that was obviously longing for release. Though embarrassed beyond words, I agreed. So many feelings hit me at once that day, self loathing, fear, excitement (for my stepmother is a great looking lady and only 20 years my senior). She had done little that day really, just a beginning, a taste of what was to follow...she had asked me to strip in front of her, as she sat on the double bed, her tight jean clad long legs crossed and as calm as you imagine. Looking back, I guess this was the moment when our new relationship was cemented. Had I refused where would we be now? But I didn't, I couldn't. So red faced and sweating mightily I had slowly and awkwardly removed my clothing down to my underpants. I looked at her, and she just smiled and repeated that I should strip for her. The confusion I felt was overwhelming. A part of me was furious with her, furious with myself, wanting only to collect my clothes and rush off to my bedroom. I'm unsure why I stayed. Her calm demeanor I thought later had steadied me. She didn't laugh at me, though a small smile stayed upon her face as I fought my inner turmoil. Finally I did remove my underwear, and stood before her naked and somewhat frightened, unsure of myself. She bid me come closer. I was as red as a beet now, as I was suddenly aware of her as a very sexy woman. As I stepped closer to her, my feelings of anger were subsiding and being replaced with wonder at what she might be about to do next. I stopped a meter from her and she bid me come closer still. Finally I stopped scant inches from her. Her knee was very close to my genitals. My penis was beginning to engorge. Slowly she stood up off the bed, her thigh touching my penis as she moved to her closet. I didn't see what she removed until she again stood in front of me. It was a black silk scarf. Leaning into me she had wrapped it softly around my head, blindfolding me, while telling me to be still. The scarf had been a revelation. It had removed me from the embarrassment, in some way isolated me from the situation and allowed me to enter a place where there was only wonder and feeling and total focus on the little touches of my stepmothers body as it touched mine. A brush of thigh against my penis, the touch of breast against an arm. So new was all this to me I was spellbound. I didn't want to move, less I awaken and find it was only a dream. She had asked that I place my hands on my head and not move them, but to say if it got uncomfortable. She asked me to move my legs well apart. I found I was holding my breath for long periods. The next thing I felt was her hand, almost flutter up my inner right thigh and stop millimeters from my scrotum. Only to flutter like a breeze back down my left. This went on for several minutes, I could only dream in wanton agony of her touching my now swollen tumescent penis. I moaned her name in desire. I felt her hand stop and sensed her move behind me, heard a drawer being opened and wondered what next. I wasn't scared however; she had asked me to let her know if I was in discomfort so I knew whatever she was up to would no doubt cause me more delicious gentle torment. But it wasn't really torment, it was wonder, at what power a women had, and how responsive I was to her. Her fingers shimmied up and down my back, from shoulder blades to buttocks, up and down my sides so it almost tickled, from nipples to pubic hair, then back to shoulders. Down to buttocks, a finger gently probing, back to shoulders, back to buttocks, probing deeper. Suddenly her reassuring words to relax, just relax and allow it to happen. Trusting her more now I tried and suddenly the feel of cold and slippery right at the entrance to my anus. I gasped out loud, and suddenly felt a slim pressure pushing against my sphincter. I tensed momentarily but quickly relaxed involuntarily as I felt her hand creep between my legs to lightly grasp my testicles, and squeeze gently. As I relaxed, I felt my anus penetrated by whatever it was she held. I felt it sliding deeper and deeper until I shuddered as it hit what I now know to be my prostate. Suddenly there was a humming vibration, shocking in its intensity but wondrous in the pleasure it bestowed. In a few moments I felt my penis surge and jerk as she squeezed some cold gel onto it. Then her hands were ever so gently wrapped around my now pulsating member and she slowly began to stroke me. So slowly, but I knew I'd come in a few seconds. She stopped and began tugging my balls down with her slippery hand, releasing them when they were stretched and starting again, as if milking a cow single handedly. Then back to my penis, even more gently. Her other hand working the thing in my arse in and out. "Please Marilyn", I cried. "Shhh", was all she replied. I couldn't believe my desperation, I had to come, I just needed to rub a little harder than she was giving me. I tried jerking my hips into her hand to gain more friction but all that did was make her slow down even more. It wasn't long before my young body could take no more. I needed to come now! I didn't care how, I just had to come. I dropped my hands to grasp my cock and suddenly the vibrator was off and out of my arse, and the blindfold pulled off. And suddenly here I was back in the present. "Hold on for just a sec Mike", She said, " I'll just get a tissue to wipe your cock for you." Somehow I stopped myself from jerking off all over the floor. Thinking that once she had the tissue she would finish me off. A few seconds later there she was dabbing at my sensitive cock with a paper tissue. "But I haven't come yet?" I demanded somewhat angrily. With a smile she looked up at me and said, "Who is training who here?" "Now", She said, "I want you to have a shower right now, and I do not want you to come until I give you permission. I know it'll be difficult but trust me. I'll never take you beyond your limits." Well that was the beginning of our new relationship. That night as I tossed and turned, unable to sleep due to sexual frustration, I wondered at what I had gotten myself in for and was beginning to touch myself, when my bedroom door opened. "Hmm," Smiled my stepmother, " I said I wouldn't take you beyond your limits, didn't I?" "Yes." I grumbled. Embarrassed at being caught in the act. "Lay back and let me finish our first lesson." She said. I did, then suddenly the same scarf fluttered over my face, blindfolding me again. The next hour was a study in frustration, gasping, heaving sweating ecstatic release that will stay with me forever. End Of Part One. Part 2 to follow in a couple of days..a lot more heavy. If you enjoyed this I'd really appreciate a vote and any feedback you care to give. Thanks. Next comes NOW: The Hard Side. Stepmother Ch. 02 Now: My relationship to my stepmother had grown since those early days. Grown in so many different ways. I had learned trust and respect for both myself, and females in general. Also I had finally come to be able to talk about my feelings to someone in an open and healthy way instead of bottling things up and letting them fester away inside of me. Although I still enjoyed our sessions, which had blossomed and matured over time, I often felt feelings of desire to give my step mother a good honest Fucking. Sure I enjoyed the torment and pain that I had craved for so long, but I was still a man, and as such often felt the desire to express my manly wants in a basic and unfettered way, without all the trimmings involved in our peculiar relationship. I had broached the subject, gingerly at first, with my stepmother, but she had shown no interest in giving up her role as domme. She had grown into her role with all the relish, ingenuity and creativity I could ever had imagined and then some. There were few areas we had not now explored in our relationship. Over time I came to express my desire for a more conventional relationship with her more openly, but she remained loyal to my dad. She did however, admit to being flattered, she said, that I had such feelings for her. I tried dating other girls at the time, but I just couldn't remain interested in them; I needed to express my submissive side, needed the pain, frustration and tears that I was only able to get from my relationship with Marilyn. Unfortunately with her I was unable to express my more conventional maleness. Sometimes, though naughty, I would fantasize about raping her, or having wild conventional sex with her. Grabbing her roughly after a particularly nasty teasing session and lifting her skirt while bending her over the bed and fucking her from behind in a wild and unconstrained way. I loved those fantasies. Being teased, having no control, being taken to my limits then reversing the tables and getting revenge for the pain and ecstasy she allowed me to experience. It was early during one of our sessions, one morning after my dad had gone to work and I was on holiday, when things took a fascinating turn. I was standing in the centre of the semi dark sitting room adjoining the main bedroom, awaiting instructions when there was a knock on the door. I looked at my stepmother in horror and panic, wondering if it might be my dad come back for something forgotten in the morning dash for work. However my stepmother merely smiled at me and signaled that I should remain standing as I was, at attention, in the centre of the room. I can't remember ever hearing or feeling my pulse beat so hard; Instantly I knew we were at a new level, but I had had no prior warning and wasn't sure if I could trust my stepmother that much not to step over the bounds we had created. Do I fold and run or do I remain? It was amid this internal turmoil that I noticed my stepsister enter the room. I almost fainted at the intrusion. I felt myself flush to the roots of my hair and the sweat break out upon my forehead and back. My Stepsister: Robin was 6 years older than me, which seemed a lot when I was young but now seems a trifle. She was within an inch of my own height and gorgeous! That's the easiest way to describe her. For her age she had always been sexy. She had shoulder blade length curly blond hair, breasts that were shaped to inspire desire, (I'd seen her on many occasions sunning herself in a bikini on the lawn outside my room). I'd guess they would be 34 D or very close. She seemed tall at six feet, a bum that swayed seductively whenever she walked and lovely long curvy legs that made me drool! She was a tease and I had longed to fuck her ever since our families had become one. Now here she was smiling at me as she wandered around me and went to sit on the rug at her mothers feet, her calves folded beneath her. There was silence for what seemed like hours to me, while I argued back and forth in my head, at what a bitch my stepmother was and how much I loved her, and how excited I was and how fantastic Robin looked and what a teasing bitch she was and how I wanted to fuck her, and how I was still somehow standing at attention and how I'm not just a bloody slave to everyone my step mother decides, and how I feel so good and on and on they went racing around my brain. Finally my stepmother smiled up at me and explained: "Mike", She began, " You have been wanting to have more conventional sex with me for some time now, isn't that right?" What the fuck was this I thought excitedly. "Well as you are probably wondering, Robin has expressed a desire to try being a girlfriend for you. Ages ago when your dad and I got together Robin commented on what a hunk you are. Of course you were just way too young back then, but now you have developed into a really spunky looking guy and Robin is keen if you are." "That's why I have brought her into our play today." Marilyn continued. "I have realized for some time that a conventional girlfriend probably wouldn't suit you, now that we have established our relationship together. Believe it or not Robin has been interested in S & M for some years too, and while you have spent those long months at boarding school I have been training her how to be a good slave too." I felt stunned! Oh wow this was about as good as I could ever imagine it getting. Robin just sat there at her mothers feet, smiling at me as my cock moved to half mast without even the slightest touch. Marilyn smiled. "Well," She said, "It's obvious a part of you approves. Now I think it is time for me to train Robin so she can be the girlfriend I'm sure you'd like and need Mike." "Hands behind your back please Mike." Marilyn ordered gently. "Now I'm going to dress Robin, then we will both go out for a short time. While we are out I have left the DVD loaded with an extremely erotic movie that I'd like you to watch. I'd like you to get yourself hard and stay that way please Mike. However you mustn't come! If you come then we'll have to begin all this another day." "When was your last orgasm Mike?" Marilyn asked me, a wicked grin lighting her face. "Two weeks ago Mistress." I replied a little shyly. "Well you are in for some real fun tonight, young man!" She replied. She motioned to Robin, who stood up in front of her mother, facing me. Marilyn slowly unbuttoned Robin's nighty thing, and then walked behind her, gently pulling on the shoulders of the nighty to allow it to slowly open and drop to the floor. Beneath the night dress Robin was naked, and in the rather dim lighting of the room she looked magnificent. Of course my penis began to engorge even more and I felt the heat rise to my face. My expression must have been interesting as Robin let out a little laugh, causing her breasts to wobble around slightly. God she was gorgeous! Her breasts were just amazing! The blond curly hair of her pubes caught the light as she moved slightly. Smooth gently muscled full thighs, shapely calves. I wanted to fuck her or at least wank all over the place. My cock hurt it was so full. "Come over here Mike." Marilyn ordered me. "That's right, kneel down in front of Robin please." She said once I had wandered over to them. My face can only have been about 8" from that golden covered pussy. I wanted to bury my face between those soft thighs and make her scream for release! As I was dying for it now. Marilyn passed me a soft frilly pair of panties and told me to put them on Robin. Robin just laughed, and lifted a pretty foot so I could slide them onto one leg then lifted the other so I could do likewise to the other leg. 'Fuck this!' I thought. I allowed my fingers to glide lightly up her legs as I lifted the panties. She slowly let her legs spread a little, giving me a glimpse of a moist pink vagina. I didn't want to go too far teasing Robin, as it might back fire on me later, so I allowed my hands to move to the outer edges of the panties and brought them snuggly up to cover her delicious cunt. Handing me a sheer bra Marilyn bid me move behind Robin and fit that as well. As I stood behind Robin, I found it very difficult to fit the bra without leaning forward quite a bit, so I could reach around in front of her and try to fit the bra to those magnificent creamy breasts. The end result was that my penis came into contact with Robins bum, which she immediately began moving slowly from side to side, teasing me even more. By the time I had attached the bra I was breathing harder than I should have been and my penis was really beginning to engorge. Marilyn sat on the bed stroking the cheeks of my bum softly, firing me up even more. Finally Robin was dressed and the women were ready to go out. "Now don't forget Mike, I want you to be primed and desperate to come by the time we get back. The movie's two and a half hours long. Enjoy!" She said with a grin then turned to leave. "Enjoy yourself Mike!" Robin said with a laugh as she followed her mother. Marilyn knew she could trust me, because she knew that I would get the most enjoyment if I tried to do as she asked of me. And I did. For the next 2 hours 23 minutes, I tried to keep myself on the very edge of coming, but without falling over the edge. The DVD made it pretty easy. It was a good story though nothing like as interesting as my life in reality was, but after two weeks of abstinence it was a real challenge to stop myself from just thinking to hell with it and allowing myself to come. My cock was pretty much leaking pre-cum constantly by the time they returned, and I was beginning to feel very edgy and frustrated. Marilyn entered first and went over to shut off the DVD while telling me to once again stand at attention. Robin entered a minute later, her short dress swinging around her sexy thighs as she wandered directly over to me and grabbed my hard cock and gave it a quick couple of strokes. "Fuck!" I hissed. "Mmmm." Robin replied, grinning mischievously. She then walked over and stood by her mother. Marilyn put on some music. "O.K." Said Marilyn, " We need to get started, so lets briefly discuss our aims here again" "If you two are going to get anywhere as a couple then we need to climb through all the ingrained social niceties and establish parameters around which you will both be comfortable." She continued, " Therefore I have worked out a method, deliciously evil that might speed you lovers on your way! We begin now!" "Robin," She asked, "Please strap Mikes arms behind him as I have shown you and while you do that tell me why you think we are bothering to secure him when we know he will do as we order?" Robin took some Velcro straps approximately 50mm wide from her mother and approached me. She still wore the very short yellow dress she had when they had left me, and with her heels on, the effect was outrageous. Well defined calves leading to utterly gorgeous thighs, braless and flowing rather than walking towards me. My cock spasmed and she just let a bubbly short laugh escape her grinning mouth. "Turn round for Robin please Mike." Marilyn ordered. I did and got my arms in to position, feeling a thrill as the unbelievable kept unfolding around me. The position for my arms was to have then folded across my back, parallel with the floor, my right arm on top of the left and each hand gripping the other arm up near the elbow. First Robin took a couple of thinner bands and closed them around each of my thumbs and circled the balance around the other forearm so effectively ensuring I could not move either thumb and that each open hand was securely attached to the other forearm. She then took the 3 wider Velcro straps and placed one around each of my wrists and opposite forearm, one near each elbow joint, before finally placing one in between the other two. My arms were effectively now joined to each other in 5 places. As she set to her first task Robin spoke to her mother expressing ideas as to why they were tying me... "I guess the feeling of helplessness heightens his excitement?" Said Robin. "That does plays a big part in it love, but there is another reason that is more important still." Replied Marilyn. "Hmm maybe to ensure that he has to take whatever we want to give him, ensure he knows he is totally helpless and vulnerable?" Tried Robyn. "That's close to it but it is really because, and Mike will confirm this, if we left his arms free there may come a time when he would try to prevent us doing any more to him, and to allow him to ruin his experience. Sounds backwards in a way, I know, but by tying him we are effectively saying to him that we will take him where he really wants to get to, regardless of his moaning he has to accept it. That's the trust. From experience Mike knows I will take him to where he needs to be and no further. That's one of the reasons we don't do this too often, it would be too desensitizing to Mike's sexual organs. He gladly goes without orgasms for as long as I dictate because he knows now that I wont starve him too long and when he does get to that place he wants to be it is just out of this world. Is that right Slave Mike?" Marilyn asked. "Yes Robin, Marilyn is right there, strange as it sounds. I love a little pain but only so much and that is not a lot. But gently, over time with Marilyn's help, if I take the little pain then it steps up in a controlled steady way, there seems to come a time when I kind of enter another space. Maybe it's the endorphins begin to really fly, I'm unsure, but that feeling is unlike any other and combine it with a prolonged orgasm or repeated orgasms and the feeling is just mind blowing!" "Wow," Said Robin, "I know some pain is pleasurable, I like it a little too, but I much prefer to give than to receive!!" This last was said with such an open friendly grin I felt some of my apprehensions fading. "Enough," Said Marilyn, "Lets get this dance alight! Robin tie his feet to the eyebolts in the floor." Robin had me strapped to the eyebolts in a jiffy, legs well stretched apart and very vulnerable. All the while my penis jerked at the way the tight lycra dress slid even further up her thighs as she bent to tie me, the sight of her breasts near bursting out of the V of the neckline. It was almost obscene that dress, and what it did for her! "Now grab these Robin and lets get Mike dressed properly." Marilyn told her daughter. Indicating a steel ball stretcher and a Teflon cock ring. It didn't take long before Robyn had the cock ring on me and the two halves of the stainless steel stretcher screwed together on top of my ball sack. The ball-stretcher itself was probably about 25mm long but it was quite a lump of steel and weighted quite heavily, sitting atop my balls. It didn't cause me too much pain though, just a slight ache that turned me on more than anything; Made me very aware of my balls and their vulnerability. "Would you like to get changed Robin?" Marilyn asked. "Mmm..." said Robin, as though considering, then, "O.K." When they returned Robin was stunning in a little black frilly French Maid outfit...the dress riding well above mid thigh, it featured a low V cut up top, with lots of lacy frills. To complete the outfit she wore black mid heel shoes. That added to the maid look. The strange thing was that the maid look made her look less of a domme and more of a slave which made it easy to imagine every French Maid fantasy you could think of...all of which served only to harden my cock even more!..... Part 3 to come...Never thought it would be this long!