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This story is a twist on another I wrote with quite a bit more detail this time. It features a sissy, prostate play, cei, brother/sister incest, and throws in a slight dose of cbt. Overall, still a loving story of two finding their soulmate, they just didn’t expect to find it in the family.
I have two siblings, both sisters, and while one is only 3 years younger than I am my youngest sister and I are separated by almost 12 years. We joke that my parents didn’t mean to have another child, but just kind of happened. Yet even with the age the baby of the family and I are incredibly close. It is likely due to the fact we grew up so many years apart, including her being seven when I left for college, that we never had a sibling rivalry or fought, and me often being the baby sitter it allowed us to form a tight bond. This was especially true as she navigated high school and would talk to me about anything and everything. With me as her confidant it was no surprise to my family when her number one choice for college was the major university I taught at or that after she got in I quickly agreed that she could just stay with me in my ranch style house I just bought.
A little about me, at almost 30 I am currently without a serious girl friend. While I am rated at 4.5 out of 5 hot peppers on rate my professor I still had not found the one yet. My college is known for our med school as much as we are as a party school which attracts both some brilliant and jaw dropping attractive ladies. That leaves me with plenty of smart bombshell ladies that take my classes. This includes a few each semester that I enjoy the very low cut blouse they wear to class while being slightly bent forward over the desk. There is usually one or two at times that will also sit in the front row wearing a very short tight skirt and do a very slow drawn out uncrossing of their legs to ensure I see the material and color of the panties they are wearing! While I could ravish these ladies every day in my office I love my job and will not risk it to sleep with one of my students no matter how unbelievably tempting they make it. Though that does not mean that I don’t let them know they have gotten to me, especially when I am repeatedly shown some very sexy panties. When this happens I will stand directly in front of their desk and while a bit uncomfortable I will let them watch a little of my growing bulge as I think about what they have been showing me all class. Then I return back behind the lectern to make direct eye contact and smile with them again. No sense not letting them know I am both a very hot professor and also well endowed. I love that I start to see their hard nipples poking through their blouse and the next time they uncross their legs I can see a clear glisten has formed. This tells me I am not the only one that will need to relieve themselves very shortly after classes end for the day.
While being well endowed and attractive might make you wonder what is wrong with me and why I haven’t found the “one” so I will share that it is two fold. As I have continued to get older the people around me stay the same age. It is very hard to meet someone in a college town that is not already married or is not an undergrad. I have dated a few brilliant and gorgeous grad students in other programs from the one I teach in, but none quite right yet. To the quite right yet, much of that comes from a lack of being able to keep up with my sexual appetite.
By far my love language is physical touch and I do enjoy curling up on the couch and holding hands; however, I love sex, really love it, from missionary to the kinkiest of fetishes I want to explore it all. As an example, one of my favorites is prostate play. I love my tight back side stretched by multiple fingers with a come here motion lifting me to new heights. I had an ex that introduced me to this in college and could make me erupt just by fingering me. It was amazing to say the least! It has been hit or miss since then if my partners are willing to try doing it with me, with none making me cum without myself or them stroking my hard cock as well. On the more extreme fetish, I have not been able to find the right person to share how hot it gets me to slip into a silk or lace thong and pound my ass with a dildo while I listen to a sexy mistress talk about pegging me with their strap on. I like to get it wet for them by gagging on it a bit and even like when they go a step further to slight sissy humiliation, nothing too demeaning just light fun, and add in cei where they “force” me to clean myself up using my tongue. It is so hot to me to give up the dominate role and give control to my partner.
With both of these I have had such mixed success in relationships with all ending. Some think I only want them for sex, others think I am far too kinky with what I do share, and I have had a couple when anal play came up decide I am suppressing being gay and should be okay with who I am. Mind you, I am very much happy with who I am and am not gay. With the pegging and slight sissy porn I really like I would probably get into the love of my life “forcing” me bi every now and again if they would really get off by watching me, but I love breasts, love sucking on their nipples, and I love the look, taste, and smell of pussy with my absolute favorite thing to innovia escort do is to go down on my sexy lady. Giving up the dominate male role is about my eventual pleasure, but so much more so about my partners pleasure, excitement and satisfaction.
Enough about me for the moment, while I am still looking for the one I was so excited to have my sister move in with me. Beyond how well we got along it didn’t hurt that she was by and far a 10. She worked out just enough to have the perfect size and toned ass and waist, perky c-cup breasts, long black hair that looked as good styled, in a messy bun, or in a pony tail, these incredible Hershey kiss eyes, and full sexy lips with a perfectly cute nose. She was also brilliant and was set to ace through the pre med program she wanted to pursue. All in all she was the total package.
I had no plans at all of acting on having this incredibly sexy young lady in my home, but I was looking forward to her and the friends she made jumping in my pool in the back yard or her just hanging out in comfy clothes only I saw on Saturday morning. Probably makes me sound like a bit of a creep, but it just comes from not finding my one yet and being a guy that appreciates beauty.
The other thing I was really excited about is that my sister truly gets me. She doesn’t know it as surprisingly I have been afraid to share my own fetishes, but her and I have had long talks about her sex drive and her feeling that there was something “wrong” with her due to the kinks she has found herself enjoying most. While her generation are certainly more liberal in their sexual beliefs, there is still this cog that is stuck on the males playing the dominant roles in bed. She has told me all the high school guys just wanted her to give them oral in a car and they were not worried about her satisfaction. Due to that she refused them all and is still a virgin. However, through her own forming sexual appetite and personal exploration she does know she wants to take charge, throw in a little femdom including spanking and slapping her partners balls, really give a guy a rough strap on, and told me about how every so often she cums so hard watching a mistress force a guy to suck and then be fucked by a another guy.
Turning 18 a bit before her graduation she couldn’t wait to get to college and explore. While I probably shouldn’t know as much about my younger sisters sex drive I do only in an effort to make sure she knew she was normal, had kinks others have, and that the right guy is out there for her to try all these things with. It gave her a safe outlet to share and also served to tell me there were ladies like me out there for me to meet.
Now granted after learning all this I would be lying if I told you my mind never slipped there at night playing with myself. I tended to get off so hard thinking of her and usually feeling a little bad after knowing she is my sister. It was a cycle, but I was still so excited to see her everyday instead of just on FaceTime a few times a week.
Move in was uneventful as it went really smoothly. I wanted to make sure she had her space so she had her own room, bathroom, and office space on one side of the house. This allowed her to feel the independence and not feel she had to check in with me. It only took a couple days after she moved in for us to get in a groove with our schedules. I made dinner nearly every night as I loved to cook and most nights of the week we had a later dinner together before she did school work or a couple times to meet up with new friends.
I also made up her office space to give her a private retreat so besides just a desk the room was able to fit a love seat and TV in it as well. I had my own sitting area in my bedroom as well and I planned to use that at first so she could have the family room, but the first night in there she dragged me out of my bedroom, told me to enjoy my tv, and watch a movie with her as she sat on the couch right next to me. I had to stop myself often from admiring her long tan legs or perfect feet and toes with red nail polish as she just had an oversized t-shirt on and what I imagined were only panties underneath it. Even with this we ended up talking for hours until early in the morning instead of watching a movie. I was exhausted the next day, but it was completely worth it.
Over the first week it was clear she was really enjoying living with me, seeing me every night, and seeing me on the mornings when I taught later in the day. She had made a few new friends, but as an introvert she had always liked being at home more so we spent most nights together on the couch, myself grading and researching and her writing and studying. Pair that with her being comfortable around me and myself a single male you can imagine after the first week I was so worked up and horny I couldn’t believe it.
Aside from being worked up by her personality and how great it was to talk to her for hours my physically attraction to her was also through the roof. She was always so well dressed, with just a touch of make up, and absolutely beautiful for her classes, but it was a whole other level I got to see as she dressed down and threw her hair up for the night. On the first night she needed to better concentrate and used her office space I couldn’t wait istanbul escort until she was done. I had a fantasy brewing in my head and amazingly it blew that away. I stayed up past midnight and she came out wearing little booty short pajamas that barely covered her toned rear and a tight camisole with spaghetti straps and that barely covered her stomach and breasts. This allowed me to see her ample cleavage in ways I had never seen before and I could see her hard nipples poking ever so slightly into the top. It was clear she was nervous at first to let me see her, I don’t believe due to a lack of confidence as she knew she was hot, but it was clear she wanted me to like it. She got her answer as I couldn’t speak or take my eyes of her. I simply wanted her so badly I almost got up to kiss her and before I could she released the cutest giggle, blushed, and sat right next to me as she asked if I liked what I saw before resting her head on my shoulder and watching the end of a movie with me. I could feel the pre cum leaking into my boxers and my cock struggling uncomfortably as it swelled. I could feel her head look down at my shorts and heard the slightest gasp as she saw my forming bulge in my shorts. Her hand moved to my knee then pushed up my shorts a little so she could rest it on my thigh. We didn’t have to speak about it as she knew she was driving me wild and it was clear she was loving it.
I am not sure if it was a confidence thing or if she just liked me telling her so everyday in a heart beat of seeing her I would tell her how stunning she was. Whether she was beautiful in an outfit, how she did her hair, or her jewelry it didn’t matter as I loved it all. This led to me counting down the minutes in the day as I couldn’t wait to get home and see her. Not even for how sexy she would look, but just to have more conversations with her, whether deep or fun, no matter if it involves playing a game, talking and especially the last two nights after she wore the camisole she kept wanting to talk about her sexual kinks. It was the relationship I wished I could find both in how I felt everyday wanting to be with her and how she had me pent up ready to explode.
I had to masturbate so many times in the week or so since she moved in, but I didn’t feel comfortable breaking out my toy box or watching videos of any mistress. I kept it quite vanilla as I worried she would hear me or my toys so it was not all that satisfying. So you would not believe how much I was looking forward to the coming Tuesday night. She had a class from 6-9 and wouldn’t be home for dinner before that. I taught my last class at 2:00 and that gave me plenty of time to drive the 30 minutes to the Adam and Eve in the next town over for some new panties, as I hoped for some backless panties, and a new dildo that had a little more girth than my current one. I really wanted to fuck myself so good and even make it hurt just a little at first
Arriving there it turned out they were having a store wide sale so after finding a few pairs of panties, some matching teddies, and an 8 inch, thick, realistic feeling dildo with new lube I thought I was all set. However, I knew the store clerk well at this point and while she was married she loved to get me going as well. Every time I visited she would sexually tease me, sometimes I would model for her, and a couple times she demonstrated on me how to use a toy or two. She never gave me permission to cum while she was in the back room as she felt that crossed a line without her husband there, but would tell me I could cum before I got dressed to leave as long as I licked up every drop so as not to leave a mess anywhere and quickly dress so I could come out and show her my mouth full of cum before I swallowed it. This time around was no different so while the other young lady ran the front she demanded I go into the back room and model for her. I was reluctant as I told her I really needed to get home, but she snapped her fingers and warned me not to make her ask again. I stood tall and marched to the back room and stripped. She watched me slip on the satin panties I bought and spinning me around and bending over the desk she whispered in my ear, “You may be ready for this realistic dildo in my harness so I can fuck you harder than you can handle, but I think I’m going to call my husband instead to have his monster cock fill you up while I watch.” I shuddered and moaned as my erection stood tall outside these panties. She then grabbed my balls so tightly and reminded me that her sissy is to do what she says. Precum kept leaking out until she slapped my balls hard and told me to lick the precum off the desk and get home until next time.
I quickly dressed leaving the panties on for the car ride home, which felt so amazing I could barely concentrate to drive. I finally got home around 5:30 and begin getting myself ready for a couple hours of fun. I ran a bath and while the tub was filling up I used an anal douche until the water came back clear and I knew I was ready for action. I got my toy box out and cleaned my new dildo admiring how it felt including the bulging veins and realistic head. All worked up I lubed up my favorite butt plug, took some effort to pop it in and then climbing into the tub I sunk in with a sigh of relief. I had the smell of roses kadıköy escort all around me as I used a fragranced bubble bath to feel even sexier. After a few minutes of relaxing I set to work with my razor to remove nearly every bit of hair. My arms only had faint light hair on them so I focused on shaving my legs, I completely shaved my balls, all around my shaft, popped my toy in and out to shave my ass completely, and even shaved my trail to my cock, my chest, and armpit hair. Luckily I had no hair on my back so I after all this hair was gone I was silky smooth in the tub, smelled of feminine roses, and was completely clean inside and out. Getting out of the tub my next step I lathered myself up with a lightly rose scented lotion from my neck down focusing on my chest and legs. I then shaved my face and neck so smooth to keep all my hair gone. As it now approached 6:30 I was so excited to get dressed so sexily and naughty.
As I slipped on black sheer thigh highs my legs looked so sexy and it felt so good on my smooth body. Next up it got better as I slipped on a pair of silky g-string panties I just got and I tucked my balls into the pouch and my cock into sleeve on the front. It felt amazing wrapping around my growing member! The final piece of apparel was a matching silk teddie that looked amazing. It had lacey trim around the cups meant to hold b cup breasts. My mistress store clerk recommended I get some breast molds a couple months ago when they were on sale. She said it would fill the top so well in my lingerie and was bound to turn me on so much. She also gave me a bright red lip stick on the house.
By the time I got the breast molds glued in place and tugging on my nipples as they hung down and the lipstick applied I was rock hard in my panties. It was forcing my g-string so tight against my back side and sending wave after wave of pleasure every time I moved slightly. Watching these breast bounce as I moved, feeling very realistic as I gave them a squeeze, and seeing them filling out my lingerie top was amazing as always. As I then got out the lube and my new toy a devilish thought over took me and I had to go to Kylie’s laundry basket. As I crossed the house I realized I wasn’t the only one who lived there and the idea of being caught dressed this way with soft silicone breasts filling my lingerie was terrifying and exhilarating. As I got to her hamper I immediately saw a few very sexy thongs, one of which was still very wet. As I brought it to my nose I was completely overwhelmed as nothing I had ever smelled was that sweet and as I gave a slight lick precum started heavily flowing as nothing has ever tasted so good! It was incredible and I was so happy she masturbated before heading to class. I left those up to my nose and grabbed a silky blue thong and an emerald green lace panty as well. Walking back across the house I moved slowly letting the satin silky feel of my lingerie brush against my freshly shaven body, watched my breast molds swing in my lingerie, smelled her sweet nectar, and felt the butt plug shift in my backside with every step. As I walked I repeated how I was such a sexy sissy and then saw it was only 7:00 so I had over two hours to both fully enjoy and clean myself up.
All dolled up, I grabbed a couple toys, plenty of lube, and laid on the bed placing a stiff thick pillow under my lower back in a way that I could lay and see the tv screen and propped up my ass for easy access. What I didn’t realize would matter is that I couldn’t see the door way at all even though it gave someone an amazing view of almost everything if you looked in. I put on one of my favorite sensual CEI videos by Christy Berrie telling me how a good boy eats all their cum up and after 10 minutes of rubbing my hands all over my body while I watched her hot body and such a sensual mistress for me I switched to one of my new favorites, Remy Lacroix, and her pegging and self facial video that I can’t get enough of.
I watch as Remy drives into his ass with a big pink dildo and that sexy smile on her face. As I grab my own stiff cock I smother my face in Kylie’s damp panties. They smell so fresh and sexy! I moan so loudly and blurt out how I need to taste Kylie’s sexy pussy before she fucks me silly. I even moan that Kylie needs to take my sissy virgin ass as hers. At this point if she were to be home and hear this there would be no denying I was fantasizing about her. Getting a bit more turned on thinking of being caught I coat a pink dildo in lube, pop out my butt plug, and before feeling empty for too long I shove it into my desperate ass. It causes me to moan “Kylie fuck me” so loudly and ooze pre cum that it began to leak through the silk sheath my cock was in. I slipped my cock out of the fabric and grab Kylie’s emerald green thong so that as I continued to leak I smeared my pre cum all over the crotch of her dirty panties. Just thinking about what I am going to do with a new large dildo filling me up I am leaked constantly. Bringing the panties up to my face I stick my tongue out and open wide to lick it clean. After a long taste of her panties and my precum I lay them on my tongue, shove the rest in my mouth and close my lips around her panties. I place her wet panties back on my face covering my nose to keep smelling that delicious intoxicating smell. With my mouth stuffed with her panties and my pre cum, a pink dildo up my ass, plus my own lingerie, lipstick, and breasts on I had to be a kinky site to see! As I thought about being seen this way I began to thrust the dildo in and out of me wanting so badly for a partner to be the one forcing the dildo inside me.
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