by sheepisheyes » Thu Oct 05, 2023 8:23 am
My wife’s sister Sue was visiting us for Halloween weekend. Both my wife and her sister are very sexy. Nice breasts and tight little asses. Totally fuckable which is not something I would know much about. My wife has given up having sex with me. She is no longer attracted to me because I masturbate too much and act like a little wussy when it comes to sex. We still love each other but just not sexually. I should say she does not love me sexually. I find her hot.
There was a Halloween party coming up and they were both going as French maids. I couldn’t wait to see them in their outfits. Her sister asked if I wanted to go and I told her I did not have a costume. She said they had another French maid costume but it was pink not black like theirs. I got hard just thinking about it and turned red. I lowered my head and she laughed and said “I bet you would look adorable. Why not, its just for fun.”
My wife was watching my reaction too. They both could tell it was turning me on but acted like it was no big deal. That evening they came down wearing their maid outfits. I could have played with myself on the spot. They looked amazingly sexy. If only I was man enough to bend my wife over and fuck her right there. But alas I would have to settle for a wank. Sue handed me the pink maids outfit. It was more like a petticoat dress. She also handed me a pair of pink panties and said “Go on put these on, I know you want to” and smiled knowingly at me.
I went in the other room and put on the pink panties and the dress. It was very short and full of white ruffles under the skirt. It came to above my knees. I felt like a sissy. My little penis was rock hard and the nylon panties could not contain it so I was poking them out like a little tent. I walked into the room and they both gasped and said I looked precious. “We need to get some stockings on you to hide those hairy legs. Lift up your skirt so I can see your panties” my wife said. I was bright red and felt so humiliated, but I lifted the little skirt up and showed them my tented pink panties. “Oh my” Sue said “It looks like you are enjoying being a sissy maid”. I looked down sheepishly and mumbled yes. “ We can’t hear you”. “Yes” I croaked.
“Let me see you curtsy” my wife said. I picked up the sides of my skirt and gently bent my knees slightly. “Very good!” they both laughed. “I can see your little tent in your panties. I think you need to take care of that. Here” and she handed my a little jar of Vaseline. “Right now in front of Sue? Its so humiliating” I whined. “Oh please. Look at you, you’re wearing a dress and pink panties acting like a little sissy, I’d say your beyond humiliated.” Sue replied “I don’t mind. Go ahead and play with yourself sissy”.
So I sat on the floor, lifted my frilly skirt and pulled out my penis and started stroking right in front of them. The were both getting their costumes ready and barely paid any attention to me. Sue started putting on her black fishnet stockings. I could see her French cut white lace panties, and her bush encased peeking through the panties. I started to groan as they both looked up at me. “Don’t make a mess of that dress. Pull your panties over your penis and come in them when you are ready” my wife said. Which I immediately did as the watched me fill my panties with a load of cum. I was so embarrassed and turned on. The panties were filled with my sticky cum and it was soaking thru them.
“My my those are definitely sissy panties! Look at all that cum, I guess someone really likes being a sissy” Sue said. I pulled my hand out of my panties and started to take them off, “Oh no you don’t. You’re leaving that sticky mess right where it is. That’s what sissies do” my wife exclaimed. I didn’t mind really. I kind of liked having a sticky mess in my panties.
The girls were all ready to go in their short skirt French maid outfits. Fishnet stockings with garters and high heels. If only I were a real man. I on the other hand I had white stockings with black shiny mary jane shoes, a blond wig with a red bow. Sue put makeup and lipstick on me which made my little penis get hard again in my wet panties.
We arrived at the party. Fortunately, I didn’t know anybody but there seemed to be a sexual theme to how people were dressed. Playboy bunnies, cat woman suits, little red riding hood. The men were also very handsome. I tagged along behind my wife and Sue. An attractive man came up to my wife and started chatting. My wife looked up at him with a sensual look and would touch his arm. She called me over to introduce me as a sissy and then ignored me. His name was Brad and he didn’t even acknowledge me. I felt so small and pathetic. Brad was clearly interested in my wife in her sexy little costume.
My penis was very stiff again. One man reached under my skirt and grabbed my pantied crotch and noticed how wet my panties were. I was afraid he might bend me over right there and fuck me. “My my you are a little sissy. I can feel your hard little clitty is all wet, did you make a mess in your panties?” he said. I moved away and noticed my wife in the corner being very close to Brad. I wanted to play with myself so bad. My sister in-law Sue was also warming up to an attractive young man dressed as Dracula. I had a feeling I was going to be the only one not having sex tonight.
As I guessed, the two men were coming back to our house with us. I had no say in the matter. They drove in their own car. On the way my wife was breathless with excitement. She told me to stay out of the way. She said if she tells me to, I am to leave the room and go to the guest room and play with myself. I was hoping I could watch her.
Brad came in an sat on the couch with my wife. She leaned against him and he placed his hand on her fishnet stockinged knee. I could tell she was turned on. “Sweetie bring Brad and me some drinks will you?” she asked. I curtsied and said of course and went and made drinks for them. I heard my wife say isn’t she a good sissy. My little cock was pitching a tent when I brought them their drinks. My wife stopped kissing Brad when I came in. I handed them their drinks and my wife placed her hand on Brad’s crotch and starting rubbing it. I stood there in my pretty pink dress as she said “ Get on your knees and show Brad what a proper sissy you are”. I was weak in the knees so I quickly kneeled between his legs knowing exactly what I had to do. She undid hit pants and slid then down. She took his hard cock out of his boxers and said “Good sissy get him ready for me”
I have never sucked a cock before. I scootched forward and lowered my mouth onto his massive cock. My wife held is cock in place as I started to bob up and down on it. I could feel my little cock squirming in my cum crusted panties. Brad leaned back and sighed as I gobbled down his meat stick. “My my you are better at this than I thought” my wife said. “You better slow down. I don’t want you getting a mouth full of cum that should be in my pussy”. She pushed my head away and straddled his lap. “Guide him into my pussy, sissy”. She slid her panties to the side under her French maid skirt as I held Brad’s hard cock and pointed it into the opening of her dripping wet pussy. She sat down on his hard cock and her wet pussy made contact with my hand. “Now go on upstairs and make another mess in those sissy panties”
As I went upstairs I could hear Sue in the bedroom begging to be fucked harder. Here I was in a pink dress and panties about to play with myself while real men were pleasing my wife and her sister. How pathetic. As I lay on the bed with my hand under my frilly dress masturbating and listening to both my wife and her sister begging to be fucked, I started to think about sucking Brad’s cock. I was getting harder thinking of his thick cock in my mouth. I snuck down stairs and watched Brad fucking my wife. By now she was on her back. They were not just fucking they were making love. She had her arms and legs wrapped around him and was kissing him as he slowly thrust himself in and out of her. Something I was not capable of. I realized I was jealous that I was not on my back being fucked. I truly was becoming a sissy.
The next morning the guys had left and Sue and my wife had changed our of their costumes. I came downstairs still wearing my sissy outfit. “There’s our sissy. Your lip stick is smeared, did you enjoy sucking Brad’s cock last night?” my wife snickered. In a little girl voice I admitted that I did. Sue said “Do you want more than just oral sex?”. I nodded my head as my little cock started growing. “Wait right here” and she went upstairs and came down with a rather large dildo. “I always pack this just in case I don’t meet any studs to take care of my pussy. Would you like me to fuck you with it?” I was stunned. “Yes please!” I whimpered. They both laughed. Sue handed me the Vaseline and said to get the dildo nice and lubed up leave some in your hand so you can play with yourself.
“Now lift up your skirt and bend over the table” Sue said. I pulled my little sissy panties down and bent over resting my stomach on the table. She started to slide the dildo along the crack of my ass and then slowly began penetrating me with the head of the dildo. I cried out like a little girl, it was as if my voice changed all by itself. “This will hurt at first but you’ll get used to it. All sissies do”. Slowly she thrusted the dildo in and out each time going a little deeper until finally the dildo was bottoming out against my ass. It started to feel so good, my little cock was hard as a rock and I didn’t even touch it for fear of cumming. My wife was watching the whole thing in amusement.
“Look at you. I can’t be with you anymore. After having a real man and seeing you in a pink dress and panties, sucking my boy friend’s cock and masturbating to him fucking me instead of trying to stop him and now watching you getting fucked in the ass with a dildo is just too much. You are a pathetic wussy. I think Sue should have you as her sissy maid. I am moving on”. Sue increased the tempo and soon I began begging. “Please make me your bitch! I want to be your bitch!” Sue just laughed and rammed the dildo as far up my ass as she could and my little penis spurted on to the floor without me even touching it. They both started laughing. “There you go then, you are officially my sissy bitch” Sue said.
My wife divorced me and I moved to Florida with Sue. Sue is very wealthy so I stay at home and wear my sissy outfits and clean her house. I am a sissy maid. We are not sexual but she doesn’t mind me playing with myself whenever I am done with my chores. She got me my own dildo and will occasionally peg me while I jerk off. She has a very active sex life and has many different men bedding her as I listen to them make love. My ex-wife has moved on from Brad and is dating a black man now. I can only imagine the size of his cock. I am sure she is finally being satisfied by real men. I even heard a rumor she might be pregnant with his baby. I am so happy for her. I will continue my sissy existence as long as Sue will allow me.