Introduction:
We moved into auntie’s place, who is desperate for sexual relief, she being single. Dad discovers me dressed in auntie’s clothes and makes me fuck the neighbor and more. I am still in college and have friends who think outside the box.
Once I started to visit her drawers on a regular basis, I had more regular orgasms that made me want more. Her panties were so soft and silky that I would get hard just thinking about them, kind of like being in love with my auntie. And knowing how I could feel her through the smell of her body left on the lingerie I could tell she was hot; she wanted the highest form of sexual passion that she could get.
Even though I knew I would be an easy lay for Harry, I hoped that I could tease him and maybe her into an extremely high and hard state that we all would be happy about. Daddy got sidetracked about young boy sex and his sister, my auntie was about crossing the gender boundary, they did this with Harry. She was bisexual from her childhood, and I was also in that path knowing that sucking a cock was just as pleasurable as sucking a pussy.
My auntie loved her pussy to be sucked and licked, especially by a male, her nephew, who wantonly lives the other side of being a male, near the female view of seeing the world of sexual satisfaction. To be penetrated is the first thing, pretty much, and then how does one enjoy the friction between the probe and the enclosing human flesh.
My butt was never the same after Harry and Daddy made me their queen by getting off in my ass, and making me love it, as they kissed me deeply and made me suck their lips and taste their cum as he fed me his cock covered with his cum from my ass, breeding me in a sense. The three of us had many orgasms together and ate freely of our fluids, aunties smell made me grovel in the animal consciousness of base human sensory awareness she tasted so good.
We used to sleep together in bed and wake up in the middle of the night with our hardons poking each other in various places. I loved getting fucked in a sandwich with Auntie giving me her luscious tits to suck on and Harry and Dad fucking my ass till I would cum on Aunties stomach, lick it off, and share some with them all. She was always ready to then sit on my face, so I could tongue fuck her pussy and swallow her juices running down my throat.
One day Auntie was home alone, and I came home from college unannounced and found her dressed in lingerie watching a lesbian porn video while getting herself off. She heard me coming in the door and shouted out to come into her bedroom where she was splayed on the bed with a big dildo up her pussy, moving her hips in rhythm to the music on the porn video. I looked at the screen and saw two trannies getting flogged by two mistresses with some short whips that were making their asses framed by their pulled down panties red.
Auntie said, “Nephew, would you be my tranny slave, can I dominate you into submitting to my deepest darkest sexual depravities?” I nodded slowly as I looked at her watching the video and getting off on the idea of her being in command. I needed her to lead me into the depths of her desires, unbounded by societal norms. I was also looking to be released from our constricting norms, especially when it came to crossdressing, I so wanted to crossdress with my friends from college, it would be so fun to party with them.
Maybe they would be interested and maybe Auntie could make us all submit. Auntie could see the wheels turning in my head, she suggested that we get a shower and wait till my father came home. After my shower Auntie called me into her room, she said, “I have a sexy outfit I would like you to try on, it was a maid uniform with stockings, girdle, bra, slips, and ruffled skirt and heels. I was drawn to the garments laid out on the bed. Auntie said I first had to go back into the shower and shave all my body hair off as close as possible, especially on my face. Once out of the shower she powdered me and put on somebody lotion which made me smooth. Then she had me put on the lingerie and sit so she could make up my face.
I loved the look as she gave me a feminine workover and then a blonde wig, with long curly locks. Once this was finished, came the blouse and skirt, and heels. They were high, I had trouble walking in them. Then she gave me a duster and said, “ok sweety, time for you to do the chores, start cleaning and don’t miss a surface your father will be home any minute and I want the place clean.
After a while I got into it, feeling like a sexy slave that is taking care of his aunty. My mind was drifting in the sexual delirium of the moment, until I heard the front door open. My father was standing there with an open mouth, big eyes, and a smile from ear to ear. He acted like he saw his dream child. Coming into the living room, my Auntie was sitting on the couch sipping her martini and looking through glamour magazines. She saw my father and smiled and said, “brother I hope you like what you see,” my father nodded affirmative, he responded with, “where did you find her, she looks beautiful, kind of makes me harden up a bit. Auntie said, “don’t you recognize her, she is from around here”, my father took another look. Then he had the look of cognition and came over and kissed me deeply, knowing I am his son but not knowing the whole deal.
Dad put his things down and asked Auntie what is up for this weekend. She said, “Brother I have a proposition for you, knowing how you love to taste the extreme side of sex in an orgy setting. I have invited your son’s four college friends and Harry over for the weekend and I am going to be your mistress who will have my way with all of you at once, how about that?” Dad looked at me we both smiled as we felt like a kid in a candy shop and wondered what events we were about to jump into. Auntie told my dad to go shower and shave everything neck to toe. He wandered off to carry out his tasks.
Auntie told me to call my friends over and go over and get Harry directly. Well, this was easy to call my friends, I simply texted them in a group text. “Guys, up for some tranny orgy fun with my mistress aunt this weekend, come overdressed and ready to stay.” They all affirmed in 30 seconds, and then I was off to Harry’s who lived 4 doors down on the same side. I pass Joanne walking down towards my house, Auntie’s friend who looked at me real hard, trying to understand what male is dressed as a tranny. Our eyes locked and then we were past each other, I did not get called out on the charade, good thing.
I arrived at Harry’s and knocked on the door, there was a long delay and I finally hear him opening the door. He looked out and saw me fully dressed and intuitively knew it was me. Oh, my sweet Brucy, some right in, and I ran into his house to get out of the street, hoping no one would see me. Once inside I got a full view of his outfit, which was kind of old ladylike, he was dressed in a skirt, stockings, low heels, a white blouse with ruffles, large boobs, a wig, and makeup. I said, “when did you start dressing like this, I love your outfit.” He said, “when I was about 10 I got into my mom’s clothes and started getting off on dressing like a female.” I have been doing it for 50 years since then, and love it as much as I can get, but I do not go out.
He looked me over and said, “your dada had told me you were into crossdressing and I see you look genuinely nice and it fits you and your build and personality. “How was it coming over to my house?” “Well, I passed Joanne from across the street and she gave me a hard stare trying to recognize me but she couldn’t.” Harry said, “Oh that old lesbian has been trying to see what her neighbors have been up to forever, I see the females who visit her house, they are always well dressed and have on sexy outfits. They come in and then leave after several hours.
Occasionally she has a weekend party, and they stay all weekend, never any males though.”
Then I knew why she was looking at me, she wanted to see if she could hook up and suck my pussy, which would have been fine with me. Anyhow Harry and I were to go back on the street dressed in our tranny outfits, to go back and get with Auntie. Harry brought a bag full of stuff and out the door, we go, as soon as we turned toward my house, who is coming the other way, but Joanne, she was about 500 feet up the street, just about past my house and in the dim twilight she was staring at us two real hard. We slowed a bit but kept moving, looking like a couple of whores out for the night, giggling about something we were about to do or say. Joanne got about 50 feet in front of us and she blurted out, “Harry that is you, I can’t believe what I am seeing, you look cute all dressed up, kind of like a 2-bit whore, but I like the look.
And who might you have walking beside you down this street, do I know you too?” I looked away hoping she would drop the issue and no she did not. We got to about to cross her path and she stopped us and wanted to know who I am and then she recognized me, “Bruce, I can’t believe what I am seeing, you look cute and sexy in that outfit.” When did you start dressing, it looks like it becomes you?” I felt like melting right into the sidewalk and a side effect was that my cock was getting hard in my panties covered with my girdle.
She then started to go on about how society was loosening up and men could dress however they wanted these days without any repercussions from anyone else, Harry and I both agreed heartily and said, Thank you for the recognition and enjoying our interests as much as we do, we thought you were going to call us out and ridicule our dress and report us to somebody, don’t know who.”
She said, “oh no, I fully support men who crossdress they get to feel like I do with more, they have a clitty that is bigger than mine, and an ass pussy that can get filled like my pussy, just they can’t have kids, not that I want any.” Harry looked over at her and said, “you look pretty good yourself, the years have kept you well, I also notice that you have quite a few girlfriends that come by to see you, and Joanne blushed and got shy. “Well you know I am interested in girly things, but more as a female, I am like a female sissy, I love all aspects of feminine clothes, lingerie, and loving a female, guess you could say I am a submissive lesbian and all those girls you see come over are my mistresses who have learned to dominate me in my house.
They make me do the dirtiest things to please them and I willingly oblige them with enthusiasm. If they make me scrub the house, I am on my knees, hopefully looking up their skirts and seeing their pussy through their nylon panties. I dress in a maid’s outfit like you Bruce and have to be very careful not to rip my stockings otherwise I will get a severe whipping, which I love by the way. I crave the feeling of letting go and swimming in my mistress’s desires for me.” Well, Harry and I were taken back for sure, we never expected our little neighborhood walk would be getting intimate with another neighbor.
Harry looked at me and said, “Joanne, you are so precious in that you shared your inner secrets with us so willingly, we thought you might want to join us at Bruce’s house in about 2 hours or so, you will like the party from what you have been telling us. Why don’t you come over, and dress in your best submissive garb, you will need it.” Joanne looked surprised and nodded that she would see if she could make it, and off we went to our respective houses. Harry and I arm in arm on our way to a sexual playground and Joanne alone to get ready.
Once back to my house Auntie was all decked out in her mistress outfit, she had on mostly black, PVC, with big boobs, zippers in all the right places, a hood that accented her head with a ponytail out the back. Her high heels were high, and fishnet stockings extended down from her PVC outfit to her toes. Harry and I were excited to see how she looked, so much different than when we left. I said, “where is dad, is he ready for this event?” Auntie said, he is just about ready, sit down and have a drink, Harry went over and kissed Auntie’s hand and knelt on one knee saying he was at her service. Auntie liked this entrance and said, “you will serve for sure, and you better like it, or you will be sorry.” Harry smiled a knowing look, and moaned a bit, knowing that the pain would be a perfect pleasure.
Dad came down and peeked around the corner, we said, “come out sissy, we want to see your outfit” and out he came from around the corner. He was dressed like I was, in a black maids outfit, frills, stockings, girdle, panties, ruffles, big boobs, wig, ponytail, makeup, and looked ready to suck any cock or pussy put in front of his face.
Auntie asked Harry and I what took us so long to come back, and we reported about running into Joanne and our intimate conversation. Auntie said, “bonus for sure on your way back, hopefully, Joanne will come over, I would like to dominate that bitch and make her learn a new level of submission. I have been ogling her for years and see all those other mistress whores she entertains every weekend, and she acts like nothing is happening and nobody can figure this out.
A loud knock at the door erupted making us jolt, and we knew it was my college tranny friends that were there, we all went to let them in. Opening the door, we saw 5 people all dressed as females and all looking passable. They introduced themselves, Danny, Billy, Jonny, Pat, and Betty. I said, “you all look so nice, really gorgeous, dressing in your submissive wear, and you brought along Betty, who is she. Danny said, “Betty was hanging out with us at Billy’s where we were getting ready and she wanted to come along.
She is a perfect lesbian sissy submissive and we thought she would fit in with us other male submissive sissies at this party. Auntie said, “please come in all, let’s get this party moving.” We all are moving into the living room where on the screen was a video of the last party we had, where Harry, dad, and I were servicing Auntie in many ways. All of my friends felt right at home seeing the video since they wanted to taste this for themselves.
Aunty pulled Betty to her and give her a big kiss, open mouthing her with deep tongue action. This got everyone’s attention as they got warmed up to each other. Betty was swooning in Auntie’s arms the two of them embracing tightly. I was totally enjoying the lesbian sissy scene and was getting hard feeling my descent into the abyss of subservience and submission. Betty too was weak at the knees enjoying her newfound mistress and filling her needs. Auntie pushed Betty to her knees so Betty could lick Auntie’s pussy through the PVC suit, she pulled down the zipper exposing her pussy, and let Betty lick for about a minute, Betty was so humble and licking so hard we were all stunned at her submissiveness.
The four trannies got comfortable and folks started taking off their clothes, when Auntie said, “hold everything, this is my event, I get to tell you what you can do. No action without permission, got it?” Everyone nodded and stood waiting for Auntie to say, “ok Bruce, I want you to undress all of your friends down to their lingerie. Harry, I want you to undress dad and Bruce down to their lingerie.” And we all got to it, carefully exposing the girdles, bras, stockings, panties, and corsets to our group. We were all starting to feel that sexual vibe in the air, the sissies were showing their hard cocks through their panties with more than one sliding of hands along their cock undersides to enhance the sexual tension.
I looked over and saw Auntie feeling up Betty’s big tits like she wanted to own them, pinching the nipples through the bra, making Betty whimper with passion. They both kissed again, and Auntie pulled away and spoke. “OK sissy’s I want you all to scrub the kitchen floor on your hands and knees using these sponges, and she gave us all a sponge, then the 6 of us got on our hands and knees and started to scrub while Auntie and Betty sat back on a chair to watch. Auntie had her hands in Betty’s crotch feeling her pussy through her panties, which were getting wet with Betty’s juices.
We were all hard and started bumping into each other, I hit Harry’s ass with my face and ran my tongue up his crack. Pat hit my ass and did the same, I tried to spread my legs as wide as possible. Jonny and Danny were head-to-head and decided to kiss each other expressing their sissy selves to all. Billy was alone and started to feel his cock, sitting on the floor to jerk off, and mistress caught this and said, “stop, I told you nobody does anything, even jerking off, without my permission.” You want to jerk off, then come over here and jerk off Betty. Billy crawled over and started to feel Betty’s pussy and turn her on, Betty looked at Auntie and said, “Auntie you are much better than Billy, can I please have you as my lover.”
Auntie looked pleased and said, “Danny goes over and suck Bruce and Harry at the same time and Billy came over and started sucking us both. This gave me a chance to look at Auntie and she said, “ok you can kiss Harry, but don’t cum yet.” Harry and I both were totally into kissing and having Billy suck our sissy cocks, which were about 7” each into his wide-open mouth, he was laying on his back as we knelt on either side of his face. I was getting really turned on and started feeling Harry’s boobs and him mine, Auntie did not say anything, so we kept doing what felt good.
The others were about finished with the floor cleaning and we knew this would play into our activities of the evening somehow. Auntie said, “ok now I want you all to strip down to your panties, bra, stockings, and garters, keep your shoes on. Then I want you to line up head to cock and sock each other in a large circle, head to cock, eating each other. Harry leaned over and started to suck Billy, while Billy continues sucking on him, I went down on Billy, then Jonny on me, and Dad on Jonny, and then Pat to complete the circle of 6 sissy crossdressers in a circle sucking each other. Mistress said, “ok now that you are joined, put 3 fingers in the asshole in front of you.”
We all slowly did this, and I felt so full, it was great, I was hoping to get fisted this evening and was very close to it, Jonny’s hands were not so big and I could easily open up to have him in me. Mistress said, “it looks like you all are enjoying this activity, Betty is there anything you can add to make this a memento of an act, and she said, “Everyone kiss and tongue the asshole in your face now, and then fist that asshole, slide your fit up inside that asshole and stretch it wide, feel your hand going up inside that person, make them feel invaded and hit all of their orgasm points, don’t; jerk them off, make them cum with your hand inside them.”
We all followed her direction and got our arms up each other’s assholes, stretching and pushing. Mistress then said, “ok sissies, you have done well, and she took her whip and started to beat us a bit, whipping our butts and making us squirm in pleasure/pain. I loved feeling the whip across my reddening cheeks.
We were all ready to cum at a moment’s notice waiting for Mistress to give us the word. She said, “Betty tell them what to do” and Betty said, “ok, cum now and then drink the piss from the cock in front of you.” We were over the top with depravity and thanked her. We all came at once ooooohhhh ahhhhhh, cumming is so good, as we all swallowed the cum into our throats as it filled them up and overflowed down our chins only to be pushed back in our mouths as Betty helped cleaning us up.
Then she said, “ok piss now sissies, piss as much as you can piss, and drink that piss, the warm nectar into your mouths, down your throats, moan like you miss it, yearn for it, tell your pisser to fill you up.” We all started telling our pisser, “please fill me, I love your piss, I have wanted this forever, give me your nectar, I want it so bad.”
Then Betty started pissing all over us and was joined by Mistress, therefore we cleaned the floor, so it was clean for a pissing party. As we were all pissed out, we were so satiated that we did not hear the knock on the door. Joanne had come over bringing two of her lezzy mistresses and they had just let themselves in since no one answered the door. They were standing there smiling and enjoying the fisting action and pissing, feeling their pussies, and making Joanne kiss them. Auntie looked over as she had finished pissing and said, “Well you are just in time for chapter 2, stand by.”
