Date: Wed, 24 Mar 2004 08:37:41 -0500 From: Elaine Rice Subject: Tales of a Crossdresser-Chapter 2 Names have been changed to protect the sexually promiscuous. Any similarities to relationships in real life are strictly coincidental. Please read Chapter 1 if you haven't already so this makes more sense... This begins my introduction into a world I will never forget, or regret taking part of. After a number of months of watching the video of my stepmother fucking my father, and them swapping with another couple, I was bound and determined to let my stepmother Elaine know somehow that I was interested in her sexually, but my mind was cloudy and every time I would role play the conversation in my head, something always seemed wrong. There is just no one true gentle way of asking my stepmother if I could fuck her. I want everyone to understand though, in this story you will not be reading about my penis being bigger than everyone else's in the world, or that I could make women cum endlessly at the drop of a hat, or anything that steers away from how this happened in my life. This is a recount of how my life took off as my stepmother found out I had an obsession with her lingerie. As I stated, I wanted my stepmother, I wanted to fuck the other girl, Bernadette too. She was a sexy woman. But again, even picking up the phone to call Bernie would be one hell of a risk to take. What if her husband answered? What would I say to him? "Uh..Hello, Doug? Hi, this is Kris...Is your wife home? No? Oh, can I leave a message for her? Sure...could you tell her that Kris wants to fuck her six ways from Sunday? Thanks..." I was in a sexual tizzy, and not sure what to do. I began to film myself jerking off in Elaine's outfits. I began to vocalize what I would do to my stepmother if I had a chance. This tape became hours in length. I would watch myself and jack off thinking of my stepmother. One Saturday afternoon, the phone rings at my father/stepmother's house, and I answered it. To my total shock, it was Bernie. I haven't spoken with her since my 15th birthday party. She told me that she was looking for some help at her house. She had some things in the attic she needed out, and couldn't do it herself. I nervously volunteered and drove to her house. On the way there in the car, I never even thought to ask why her husband Doug couldn't help. After I arrived, Bernie greeted me at the backdoor with a big hug, "How are you sweetie?" She said in that sexy purring radio voice that I have always known her by. She called me sweetie. Good God. "I'm doing great! Where's Doug?" I asked, mocking a look around and acting like I cared.. "Oh, He's fishing at camp up North this weekend. He is always running somewhere doing the `guy thing.'" She replied. I nearly forgot my father was leaving this afternoon to go too. I hated fishing, so I never went. We exchanged salutations and went upstairs to the attic entrance. As I went to the door to the attic, she asked me elsewhere. As I followed her to the bedroom, she was gone. As I walked into the room, the door closed behind me. She shut it, with a smile that looked both devious and divine, she seemed to light the room with her presence; she stood there in her gray sweat suit. Right then and there I knew that something was about to happen. Instinct said to me, `she didn't have to close the door behind her Kris'. My heart nearly stopped. I couldn't manage to take it all in. I just froze up. She took a few steps closer to me. "Have you been thinking about me sexually, Kris?" Bernie asked, nearing me. "Bernie, I..." "Just answer, yes or no; Would you like to fuck me?" "Uh...of course! Are you kidding? There's probably not a guy in the world that could turn your beautiful body down. He would be crazy if he turned you down." I replied. "Well then," she said, pushing me onto the bed, "I never fucked an underage guy before." "For what it's worth, oh shit Bernie," I fumbled, "I'm sixteen." My heart was racing out of my chest as she pulled my jean shorts off. I had on a pair of Elaine's navy blue string bikini panties. I loved feeling the silk close to my cock, and walking around in them felt wonderful. "Interesting..."Bernie paused, looking at me in panties. I must have turned ten shades of red, because Bernie seemed to notice, touching me through them and smiling, saying, "It's alright, sweetie; I think they're sexy!" "Really!?!" I asked. "Yes really, do you like wearing panties?" "Uh huh." "Any other things?" She asked. "Yes, whatever I can find. I just like underwear and lingerie, I don't like the makeup and wigs and stuff..." "No need to explain." "You don't think I'm weird?" I asked "I don't think you're weird. Everybody has their secrets." Bernie assured me. "Bernie, I have to tell you something now that, I have been thinking about you a lot lately, a whole lot. More than a boy my age probably should. Is that wrong?" I asked her. "No, it's not wrong. As long as you aren't hurting anyone. You know sweetie, you look older than sixteen." She teased. "Really! How much older?" "I'll see how `old' you are, don't worry." She teased, stripping her clothes off. Her sweat suit quickly was lessened to a black satin bra and panties and crawling up the bed on her hands and knees to me. My cock was quickly stiffening. She sprang my swollen tool from the top of the panties. Bernie sized me up to her liking as her hand pulled my meat gently and I became fully erect. Her mouth swallowed my tool and she worked me in and out of her expert throat. I cried out wordless moans. Ah, my first blowjob. "This is a nice sized cock! I think it will fit perfectly. Kris, have you ever had sex before?" She asked. "No. Not yet." I said, gasping as I felt her steering my tool closer to herself. Bernie was clearly very athletic. The definition in her abs, thin waist and shoulders gave her away. She held a deep tan in her Italian skin. Bernie threw a tan leg over my waist and her panties got hiked to the side. I watched in awe as my saliva slick cock entered a warm pussy for the very first time about an inch deep. She eased down onto me and as I went all the way in, she moved into perfect position over me. Bernie held both of my hands in hers as we made fists together. She leaned down and kissed me passionately on the mouth as we joined together in erotic pleasure as my first sexual experience was underway. God, her pussy felt good. "I think it's so sweet that I get to take your virginity! Kris, I promise to teach you everything you'll ever need to know to make a girl feel good. Just let me show you how" Bernie increased her rhythm to a frantic pace, and all I did was hold her hands and enjoy her tight muscles inside holding me, rocking me, urging me. I matched her rhythms. Her down was my up. She responded by groaning and cursing me to fuck her harder. I held on for as long as I could. About twenty minutes in, Bernie cried out that she was cumming, and any seventeen year old guy that hears a woman moan that she's cumming has pretty much the same response as I did. I felt my orgasm near at a quickening pace. I was pretty good at holding out on my own, keeping myself from cumming, but she was bringing me fast. "Oh God, Bernie, you're going to make me cum!" "Don't you dare cum inside me Kris. You're bareback. Pull it out of me!" She coached, "Come on, Kris, cum for me! Cum everywhere! Go on, do it! Yeah!" Bernie slid off of me and took my cock in her hand. She sat on my thighs as my tingling sensation in my groin turned to a pulsing sensation. She eased closer to my cock when the first pulse began. I hit Bernie right in the chin and lips, startling her. The second hit her D cup tits, and the remainder emptied into her hot mouth as she sucked my tip. Bernie eagerly lapped up the sperm on her chin and fingered it from her tits into her mouth. "What is going on here?" a familiar female voice cried from the hallway. Our immediate attention was drawn to the doorway as I stared at Elaine standing there glaring at us. I was shocked as my stepmother came into the room, appearing very upset. My chances of explaining anything were far gone. "What in the world do you think you're doing, buster?" I hated when she called me "buster". It really threw the wedge between our generations. "Elaine, I can explain...I...We...." I fumbled. Hell, I didn't know what to say. "No you can't," she replied, "so don't even try it." Bernie sat up from my lap. Most of my cum was swallowed. She locked eyes with Elaine. Elaine walked over to the bed and Bernie was on her knees. "You missed a spot," Elaine said, leaning forward and licking the thick gob of cum from underneath Bernie's chin. Then they French kissed right in front of me, mixing it up with their saliva. "Whoa, you mean you planned this?" I asked Elaine. "Wow, you catch on quick." Elaine replied with a tint of sarcasm in her voice, sitting on the corner of the bed. Bernie got up. I think I should have been embarrassed sitting on Bernie's bed, stark naked with my hard on standing straight up, and my stepmother in the room, but I wasn't, which surprised me. If I was at Elaine and my Dad's house and masterbating when she walked in, I would have been scrambling to gather myself up. "I think we need to talk, Kris." Elaine said. I sat up and gave her my attention. "I'm going to say this the best way I can, and don't interrupt me, just let me get it off my chest. When I started to notice lingerie of mine missing around the house, I began to wonder if I was going crazy. I knew I wore something, and when I would go to get it, it would be missing. Then I would find it, and really not give it much more thought. Then more of my things showed up missing. Teddies, camisoles, thigh highs, slips, you name it. So I knew something was going on. I never said anything to your father though, at least until I got to the bottom of it. Some of those items mean a lot to me. They were special. Then one afternoon, Bernie is over the house and asks to see our Cancun vacation video from a month ago. There is a tape in the VCR and instead of hitting Eject, I accidentally hit Play." Oh shit...I knew what was next. I forgot to hide the tape I made. "We see the downstairs, all lit up, and nobody in the camera's view, so we fast forward and the next thing we see is you, in nothing but a green silk teddy and white thigh highs. You strut around and feel yourself up through the teddy; my teddy. I wanted to throw up. You sat down and had a whole ensemble of my clothes thrown on the bed and you were using the silky things to jerk off. I felt so violated. You bastard! You, taking my things, using them for your deviant sexual desires. It was like a train wreck; I was disgusted, but I had to watch." "That's when Elaine and I started to listen to what you were saying while you were jerking off." Bernie interjected. "You were moaning out her name, and MY name too. You were all alone, dressed in lingerie, and panting about what you wanted to do with us; Fuck us, eat us, cum on us. You were saying some specific things that led us to believe that you saw the tape we made with our husbands a few months ago. The things we wore, the ways we moaned. It was disturbing and yet exciting all at the same time." Bernie explained. "So, finally I realized that you were actually paying me a compliment." Elaine said. "It took a few times watching it, but we came to that conclusion." "Wait," I finally interrupted, "you two watched it together more than once?" "Uh huh," Bernie replied, "and we had a little bit of fun together watching you." "So that's when I thought, `Why not seize the opportunity?' You have a seventeen year old boy who pounds the shit out of himself thinking about you, why not give him the real thing?" Elaine said, nearing me on the bed. She took my still stiff hard on by the base and kissed the swollen tip. My stepmother began to give me incredible head. I finally got to understand how wonderful it is to have her plush lips around my meat, bobbing away. Elaine sucked while Bernie talked. "Kris, we all must understand some things, or any of this will never work. First of all, we're married, and we plan on keeping it that way. Secondly, if you tell anyone about this, and it gets back to either of our husbands, we will never forgive you, and we'll deny all of it. Third, we don't want anyone getting hurt in all of this, especially you. You are only seventeen, so please don't start falling in love with one of us or some childish shit because that will never work. Fucking and making love are two different things. We are just two ladies that want to explore our sexual horizons. If you can understand that, and respect our wishes, we can all enjoy ourselves and one another for a very long time." "Well damn, my mouth is shut about this. I'd be crazy to say something." I replied "And one more thing..." Elaine said, coming up for air, "if you even try to think that every time your father runs out of the house that is a free pass to get into my panties, you are sadly mistaken. Your father is very protective of me, and if he sees you making eyes at me, he is going to get suspicious. So we determine when the sex is, got it?" Elaine asked. "Anything you say, Elaine. Aaaahhhhh....." I moaned as she resumed the blowjob. "Do you know how bad I've wanted you? How much I've just wanted to fuck your brains out? I can't recall all the times I had to sit there and watch you eating strawberries, bananas, and actually moaning softly while you eat one. Do you know what that does to me? " I asked her. "Probably the same thing it does to your father. I don't do that by accident." She teased. I gently grabbed her hair and pulled her further down my shaft. She began to choke on me, so I let off. I begged her to fuck me, but she refused. Bernie had Elaine's clothes mostly off. I hadn't noticed. Elaine told me that before I could enter her, I had to learn how to eat her first. She lied back and spread her legs apart for me. She had on none other than one of my favorite dress up outfits. It's a tiger print silk teddy, cut really high in the hips and has a sheer black nylon ass. I watched enough movies to know what other guys did, but I never actually ate a girl before. I lick the inside of her thighs all the way up and she nearly hit the ceiling fan with her pelvis she jumped up so quickly. I lapped away, swirling my tongue around, poking it inside her hole, licking her clit, listening to her coach me on. She taught me to be an expert at pussy eating. I then climbed up to Elaine and as she placed her calves on my shoulders, I slipped my cock head up and down a few times. "Go on Kris, do it, go on, give it to me!" she cried out. Just as I was about to enter my stepmother for the very first time, Bernie interrupted us. "Wait a minute," Bernie warned, "You can't just start fucking her like that!" "Like what?" I asked, sitting back. "You mean, without a condom?" "No, you dumb ass. You need to put something on before you fuck Elaine." "Yeah, get the bag in the hall." Elaine said to Bernie. Bernie brought a duffle bag back and emptied its contents onto the floor. Without much hesitation, Bernie picked out a black fishnet bodystocking with arms for me. "Go on, put it on, hurry" Elaine said. I got it and put it on, pulling it up and onto myself. With some adjusting, it fit on me perfectly. Thankfully, it was crotchless, so my erect cock fit perfectly through the sewn opening. Elaine pulled me back onto her, and after positioning ourselves again, I felt myself sinking deeply into her. We found our rhythm together was in sync. Although this was only the second time I had sex EVER, we worked together perfectly. I marveled at just the thought of finally getting to fuck my 40 year old stepmom. It was so nasty. Elaine moaned really loudly. I began slamming into her with a feverish rhythm, and that is when she came, crying out to fuck her harder. As she came, I could feel how quickly she became wetter from her orgasm. The change in sensations suddenly brought me to the edge. "Oh God Elaine, I'm going to cum!" I grunted. "Oh fuck Kris, cum inside me! Yes! Oh yes! Aaahhhh..." she sighed. I pumped six or seven more times and finally felt the pulsing begin. Elaine reacted by pulling my stocking clad ass closer to her. On and on I came, emptying my seed deep in my stepmother's womb. We panted as my orgasm ran its course. I pumped a few more times after my orgasm subsided and We quickly felt the juices squishing out. We laughed at it. I was so pleased. After I pulled out, I watched Bernie eat Elaine's sticky pussy out, sucking our cum down. Finally, Elaine leaned toward me and engulfed my still erect cock, proceeding to suck the combined cream from me and tasting herself to much satisfaction. The three of us got dressed and Elaine and I drove home in our separate cars. I was so absolutely crazy for my stepmother. I know she told me not to think like that, but I couldn't help but think about the experiences that lie ahead. After all, it was late Saturday afternoon, my father was on his way to camp with Bernie's husband, and Elaine was supposed to take me home. Was I going to stay until Sunday night instead?