Hot Crossdresser Stories
My Friends House Part 1
Well this story starts a long time ago. Can’t remember what age I was, but I think it was around 18.
This one time I slept over with a friend of mine. We watched a movie, played games, etc. Then his mom knocked on the door and told us it was time for bed, because my friend had to get up for work.
I saw his mom stand in black nylons with short cowboy jeans on. I kept staring at her feet, and my cock started to get aroused. She was a tall lady and had pretty big feet for a woman, but still they looked so nice. I saw my friend looking at me, and I stared down the floor, hoping he did not see that I looked at his mom’s feet. He said nothing, but I am sure he saw my cock getting hard. We said ‘goodnight’ and went to bed.
I always have had trouble sleeping over with others. So I guess I slept for an hour or 2, and went to the bathroom. I did not see his mom up, so I was sure she was sleeping too. I walked into the bathroom to take a pee. And there on the bathroom floor I saw some black nylon pantyhose on the floor. I got instantly aroused.
My body was shaking all over. I picked up the nylons and saw it was black Wolford’s, and under them there was a white thong. I took the thong up to my face, and took some big sniffs. Ooh boy, I could have exploded just there, but luckily I did not! I was so freaking horny and started licking the thong all over. Her sweet pussy juice just tasted so great. I then bent down to take the pantyhose and smelled them too. Again, I inhaled the odour from her toes. Oh my god, this women had the smell of an angel! I put the pantyhose on; they felt so amazing against my skin, just knowing she had them on 2/3 hours ago! I started to arch my feet and I felt so sexy and sissy like I loved every minute of it! I began moaning; I did not know I was so loud, because just then I heard a knock on the door. It was my friend.
He asked “What are you doing in there? Are you OK?”
I choked on my own words. “Ehmm…yes…I am OK! Just needed some air!”
I knew he knew that I was lying. I kept stroking my hard sissy cock. When I heard the door trying to open, I told him “I’ll be right out! Just give me five!”
“Yea…OK!”
I heard him doing something with the door. But I was in a whole other place and did not realize that he had pushed the key out of the keyhole because there was a mat in front of the door.
“I’m going to bed again!” he said.
I did not answer. I then started moaning again, just a little quieter. It felt so good, stroking my hard cock and almost getting caught. I came so hard and never seen myself cum that much. The bad thing was that I spilled my cum on his mom’s pantyhose! I panicked, took them off and laid them down the same spot as I found them. I washed my hands and tried to unlock the door, but I realized there was no key. I saw it on ground. Hmmmm?? I unlocked the door and heard someone running away. I went back his room.
When I entered the room, he pretended to be asleep and the blanket was not covering him all over – and I saw his cock – hard. Had he being staring at me through the keyhole, and had become hard over me? When I was in his mother’s pantyhose?
I tried touching his cock, but he turned around and snored. I laid back in bed and fell asleep like a baby.
My Friends House part 2
The next morning, after I slept like a baby, after that great wank, I stood up from the bed and saw my friend was not there. I called on him, but no one responded. I went to the kitchen where I saw this note on the table.
Hi. Just wanted to let you know that I’ve already left for work. So when you leave, please lock the door after you.
And hide the key – you know where.
I saw the key on the table. And thought to myself, ‘Hmm…I’m alone in the whole house right now!’
His mom was a stewardess on a plane, so I knew she would not come home for at least 2 days again. Wow, this is great! I turned around and headed straight to his mom’s bedroom. I went in and I could still smell her scent in the room. Mmmm, it got me hard instantly! I took my pants and underwear off. I opened one of her closet doors and saw a shelf for each part of her clothes. A shelf for panties and bras, a shelf for pantyhose, etc.
Oh my god, I was in heaven!
I was so fucking excited, I could not hold back. I took on some white g-string with lace. MMMmm! just putting them on was sexy, and just knowing that I was wearing my friends mom’s panties on. The lace felt so good around my little sissy cock.
I looked through the pantyhose she had; she had some opaque white pantyhose. I loved white right at the time. I was already moaning like a little sissy. I took the white pantyhose and took a good sniff. Oh my, this was my heaven right now! I put the pantyhose on one leg, then the other. The hose felt so great on my shaven legs. My cock just got harder and harder – I could feel it pumping. I then saw one of her stewardess’ outfits in the closet. I put the skirt on, it was a perfect match. It was a red skirt. I saw the red jacket, and thought ‘I need some boobs’. I took one of her bras and put it on. I stuffed them with her pantyhose. After that, I put the jacket on. Then when I had put on the jacket, I saw a box in the bottom of the closet. I could not resist, and opened it. There was a white wig and a red wig, like a ginger red colour. Anyway, I tried them both on, and saw myself in the mirror in the hallway. I liked the white one the best. I found some red pumps under her bed, and luckily she has big feet, because they just fitted perfectly.
I started walking around inside the house. I went into the living room, where I sat down on the couch, feeling all sissy-like. I loved every minute of it! I threw my legs up in the air and admired them from my own view. I took one shoe off and began smelling my own nylon foot – the scent from my own feet and her pantyhose was delightful. It was so good; I started sucking my own my big toe. After that, I quickly sucked my other toes as well.
I could not hold back any longer. I lifted up my skirt and saw my cock pumping in the white pantyhose. I then slid the panties under my balls and the pantyhose back over my sissy cock. I touched myself good, and rubbed those pantyhose against my cock, while pointing my pantyhose feet in the air. I closed my eyes and kept rubbing for a while – it was magical! I opened my eyes, and looked out of the window. Let me say this, it was a wall of window. I looked out – and stared in the eyes of a man that looked over the fence!
I guess he was walking his dog or something. He must have been a tall guy because I’d never seen anyone look over that fence before. I recognized him as my physics teacher!
He ducked down. I think he was hoping that I did not see him – but I did! ‘Oh my god…this was not happening!’ I panicked for a second. Then I thought, ‘It’s not me that is watching! He is…that grumpy old pervert!’
I stood up, turned around, and was acting like I did not see him. He kept on looking. I could see the top of his head over the fence. I turned my back to him and leaned forward really trying to show my white pantyhose ass. His head quickly came up over the fence again. I started moaning real loud and slapped my own ass really hard. So every time I hit it, I let out a girly scream. I saw him in the corner of my eyes that he was shaking like he was jerking himself off!
My thoughts went through my mind ‘I’m over at my best friend’s house, alone in his mom’s sexy clothes, especially her pantyhose, playing with myself all sissy-like…and there is a man watching me as I do so! How freaking hot is that?’
Right there, I heard like a weak sound almost like a grunt. I looked out of the window. What I saw was priceless! He stood there, with a grin on his face, with his eyes shot. ‘Oh my god…someone just jerked their cock for me when I’m a little sissy! MMmm!’ That thought made me cum so hard, I could not stop it! it all happened so fast! I shot my load right in this white wonderful pantyhose! It was a lot of cum that came out, and I felt it down his mom panties. And down my pantyhose legs – all sticky and smelling like cum. While all that happened, I kept staring at him. When he opened his eyes, he saw me staring at him. He fell down; I heard him stumble and run away.
This is the most awesome thing that ever happened! I hoped my teacher did not see who I was. But even so, I knew a big secret about him. I was kinda in a dilemma because I was covered in cum, in his moms pantyhose and g-string! Should I wash them or just steal them? I was heading to his mom’s room when I heard a car go into the driveway.
My Friends House Part 3
I heard the car door slam. I panicked and hid under her bed. I heard the front door open.
At this point I was shaking as hell.
‘Oh my god, what was it I was doing here? It’s fucking crazy! I’m here in my friend’s house in his mother’s clothes, covered in cum, hiding under his mom bed…and his mom is coming in the house right now!’
I almost wanted to cry right there!
I heard her going around in the house. She came in her room; I did not pip a sound. I looked to the side; she had some red high heels on with white pantyhose. Oh my, she hasn’t taken off her uniform! I had the same clothes on as she did. I instantly got a hard-on again! She sat down on the bed, and what I saw next I remember so clearly still after all these years. I saw that she was taken her shoes off one by one slowly; I was so aroused! I moved my head closer to her feet so I could see her white pantyhose feet with her pink nail polish on. Mmmmm! I could not control myself. I started rubbing my cock. It was still all sticky from my massive load of cum. All the things in my head said ‘No…this is not right! I need to get out of this!’ My heart was saying ‘YES!! Go for it. Give in to your desires. This is your moment of heaven!’
She was stretching and wiggling those pretty hosed-covered feet right in front of my face. I heard her saying “Mmmm” noises. This just got me turned on so much more! Hearing my friend’s mom making moaning sounds. Then she lay down on the bed. I took one of her red heels and started sniffing them. The scent of her pantyhose feet made me seep pre-cum.
‘Don’t cum yet! Don’t!’
Then I heard more noises from her.
“MMMM! Ooh…feels so good in my pussy!”
Oh my, the way she said it, perfect.
“I want a little slave licking my feet!”
Right when she said that I froze. Did she know that I was here? Or did she just want a slave? How should I know?
“MMmmm! He came in my stockings!”
She was talking about me, or maybe to me? I could not take the chance; it’s my friend’s mom! I stayed quiet. And she just kept getting louder and louder. I clearly heard that her pussy was wet. And right there, she came so hard that she was squirting all over the place. Then I just felt my cock going off while she still orgasmed. A lot of cum came out of my sissy cock and hit the underside of her mattress and down on his mom’s pantyhose and panties. I could smell the stench of my own cum. His mom was toning down. And I thought to myself again that ‘This is insane. And if I get out of this, I never do this shit again!’
I think that 30 to 45 minutes passed – it seemed a very long time. I must have dozed for a bit too. But I think she was sl**ping. Maybe this is my way out?
I quietly tried to push myself out from under the bed. I stood up, and saw what was lying in the bed. His sexy mother in her stewardess uniform, with those white pantyhose, and her boobs sticking out of her shirt – all covered in her pussy juice. Her juices had hit some of her pantyhose feet and some went up her legs.
‘God dammit. Why do you have to be so fucking sexy?’ My cock started to show signs of life. His mom kept on sl**ping and I heard snoring. ‘Don’t do it. Don’t do it. Don’t fucking do it!’
Right there, I sat on my knees and started to smell her pantyhose feet. I did not want her to wake up. How would that look? Me, in her clothes, covered in A LOT of cum, sniffing her feet! Ah, fuck it!
And then I took her big toe in my mouth. But when I got it in my mouth, it just tasted too damn good. I could taste the pantyhose, her sweet feet and her pussy juice, and the fact that she had her shoes on for quite some time. The combination of all those things, I lost control of what I did right then! I took one of my hands and started rubbing her feet, and the one I was sucking, I sucked on even more. I guess I must have been a little rough because she then started moving.
My Friends House Part 4
I could see that she started moving. I tried to hide by the foot end of the bed. It got quiet again. I’d better try to get out now. I came to my senses and it was enough now. I tried to take my clothes off that I had borrowed from his mom. I took off the jacket, and was just about to take the wig off, when I heard her moving in the bed again. Now she was facing towards me, but I thought she was still asl**p. I was standing in his mom’s white pantyhose, in heels, bra, and her wig. My cock started to move again.
‘No!! Not now!’
I pulled my cock out and started playing with myself in front of her. I thought she was asl**p, but just then I heard her say…
“You Better Keep Going Pulling On That Sissy Cock!”
I collapsed and started crying.
“Sorry! Sorry! I’m so sorry!”
My body was shaking like hell and I felt so ashamed of what I have done. She got angry and took me by my arm firmly. She stood me up and said “You better keep going!” She had this angry look on her face.
I took my little cock in my hand started playing with it. I kept crying; this was so humiliating.
“Did you know all the time?”
She took a leather whip. And she looked me in the eyes. “Get over here, bitch!”
I walked over to her.
“Turn around!”
I turned my ass to her.
“Now you better bend over and pull up my skirt that you just took without asking me!” She was kinda yelling now.
I must confess I was pretty scared. I bend forward so my white pantyhose ass was sticking out. She laid her hand on my butt, and stroked it nice and soft. Oh, my cock was pumping like hell! She took her hand away, and I knew what was going to come next was going to hurt! But never imagined the pain would be so powerful! I screamed in pain like a little sissy I am.
“You never ask the questions around here, I DO! Got it?!”
I screamed my lungs out “Yes yes…I’m so sorry!”
She hit me again. I could feel that she was not holding back.
“Now listen. You call me ‘Mistress’, and nothing else. Now let’s start this!”
I tried to hold my tears back and behaved as a good sissy. It was hard though.
“Stand up and look at me, bitch!”
I stood up and tried to look her in her eyes – it was tough. She just stared deeply into mine. Never ever have I felt so small in life before!
“Did you cum in those pantyhose in the bathroom yesterday? I found them this morning all filled with cum!”
I looked at her eyes “Yes, Mistress!” I looked down and wished this had never happened.
“Stick both your hands out and let me see the inside of your hands!”
I turned them around and she slapped me across my palms. I really tried to keep my hands steady, but it hurt so god-damn much. I could feel my tears building up again.
“Never do that again without asking me, bitch! You like wearing my clothes?”
“Yes, Mistress!”
“So you like dressing up to be a little slut?”
“Yes, Mistress!”
“Does my son know you are being a sissy?”
“Don’t think so. But I think he saw me through the keyhole while I was in your pantyhose masturbating, Mistress!”
She kept staring at me with this look on her face.
“You think he likes you?”
“No…I just think he is curious about stuff!”
I got another slap over my hands. I hurt so bad, and it felt like they were burning.
“Good! I don’t want him to be a sissy like you!”
I felt like something was wrong with me, and there probably is! She threw me on the bed, blindfolded me, and tied me to the bed.
“Now you stay right here and I’ll go and get myself a coffee! First, I need a shower though!”
I was too afraid to saying anything. I lay in the bed and could hear her taking a bath. I got aroused by the whole situation! I heard the shower stop, and she entered the room again.
“I see that you are getting stiff again with that tiny cock! Ha-ha!”
My body was shaking all over. Right then, she whipped me on my feet. I screamed like a girl. But then I could feel something else – I got turned on when she slapped my pretty little girly feet! I arched my foot, feeling all sexy and humiliated at the same time! She could hear me moaning and I arched my feet.
“Ohh my, you like that, don’t you? Laying there in mommy’s sexy pantyhose…Sissy girl!”
She then began to hit my feet again and again. And now my screaming was beginning to be more moaning.
“Do you want mommy to keep going, slut?”
“Yes, mommy!”
This time I got hit hard. I could feel that I was tearing up again.
“Yes What?”
“Yes, Mistress!”
“We are done for now. I’m going for a coffee!”
I did not say a sound while she put her clothes on, but I heard her putting on pantyhose – I always remember that sound. Then I heard her in the bathroom taking a piss. She came back. The next thing I knew I could feel was that she was standing in the bed. She seated herself on my face with her cunt open.
“Now clean me, bitch!”
I did as I was told and sucked her dry after her bathroom visit. MMMmm! Wow! The taste of sweet pee and her wet pussy. Again, all off this was too much for me, and I came. I felt my cock just pumping the cum out, and felt it running down my cock. I felt her stand up again. I heard her putting on her clothes back on.
“Stay here, slut!”
“Yes, Mistress!”
And heard the car start outside, and she was gone.
My Friends House Part 5
I must have been sl**ping, because the next thing I heard was like someone had taken pictures of me. I was afraid to say anything, but thought about what she wanted with pictures. This went on for 5, maybe 10 minutes, and I felt even more humiliated. Then I could feel her climbing in the bed.
The next thing I knew I got a cock in my face.
“Lick it!” I heard this was a guy with a very deep voice. I totally freaked out. “You better behave yourself, or maybe those pictures will be used against you!”
After that, my body was still shaking of fear, but I tried to calm down.
“Good girl!”
MMMmmm…the feeling it gave inside my body when he called me a girl just felt right! He was sticking his cock in my face, and I opened my mouth slowly, feeling the tip off his cock on my tongue. Wow! I’d never tasted a guy before! Right there, he just f***ed his cock in my mouth. Oh my, it was thick. I loved this feeling where I sucked a guy off, and being his little bitch.
“You like that, little sissy, ahh?”
I tried to let out some sort of sound ‘MMmm’ and he just kept on going. He was really fucking my face right now. Oh my, I was being used good! I was still tied up and could not do anything – just lying there being a fuck doll. He took his thick cock out my mouth. My mouth hurt after that treatment.
“You suck cock like a girl!”
Every time he called me something with ‘girl’ my body would twitch. The feeling it gave felt so right. I think he saw ‘me’, because after that he called me girl all the time. Then I heard the camera noises again. This time though, I got so turned on. I started to try posing while I was tied up, but could not move much.
“Oh my lord. My little girl likes this!?”
I twitched again and started moaning like a little girl.
“Arch your feet for me in those pantyhose!”
Wow! He liked pantyhose too? I just did as I was told.
“MMMmmm…good girl. You like being a little pantyhose sissy!”
My moaning got higher. I was so freaking horny.
“Little sissy is getting rock hard I see. Let me take a picture of that cum-covered sissy cock!”
I heard the camera take quite a few pictures. I felt him touching my pantyhose bum.
“Wow! I love your pantyhose-covered ass!”
He ripped a hole in the pantyhose, and then I got scared again. I asked him “Are you gonna fuck me?”
“Yes, I am! I just need a condom!” I heard him sliding a condom on.
“Please don’t, sir. Please!”
Ok, I have fantasized about being taken by a guy in girl clothing, but after all off this, I could not take more.
“Yes. You don’t have a choice! See you lying here, being bound up in girl clothing, with a blindfold on, making me all horny…you need this! So you’re gonna be fucked whether you like it or not!”
I was feeling fear and excitement at the same time. “Please do not do this, sir. I beg you. I will suck you off…cum in my mouth. Please don’t fuck me!”
“Shut the fuck up, bitch! You better take it, or the pictures…”
I did not say a word again. Then I felt his cock trying to get inside of me. But my legs were tied up, so he untied my legs. He was holding my legs up by my ankles, and he was trying to push his cock in me. But my hole was not big enough for him and hurt like hell when he tried to f***e his cock in me!
“Wow! All that cum, and still not wet enough for my cock to get in!”
I heard him spit, and felt it in my hole. Then he stuck a finger inside of me. It hurt a bit at first, but when his finger entered me, the sensation was so good! My cock got hard and I started to moan like a little girl.
He pulled his finger out – even that felt nice! He then spat in my sissy ass again. And this time I felt two fingers. God…this felt good! My moaning started getting higher and higher.
“See little slut, I knew you would like it!”
“Yes Sir!”
He was fucking my ass with his fingers. “MMMmmm…yess!”
“And since you like it so much, you are getting my cock too! Ain’t you, bitch?”
He pulled out his fingers and I felt him trying to get in – but his cock was too thick. I heard him spit a lot on it, and felt it in my hole too. All wet from his spit, he tried again. It was a painful experience – but he f***ed his way in me – and in it went. He let out a big grunt. Oh, his cock felt so good inside of me, I almost came.
“Are you ready to be fucked in your tiny tiny sissy hole?”
“MMmm! Ohh Yess, Sir. Fuck me!”
He furiously started to fuck me. There was no gentle moment – he just went all in. I screamed like the little sissy slut I was. And he just kept going, and made some noise too.
“Ohh…you love this! I can see it! You like being fucked in pantyhose like a whore! MMMmmm!”
I could feel my cock pumping – I was gonna explode soon. I almost screamed “Yes, Sir…Fuck my tight pussy!!!”
I heard the camera go off again. This made it even more sexy. Oh my, he was taking a lot of pictures!
“You like to jerk off in my mom’s pantyhose?!”
I froze…I did not know what to do! He kept fucking me hard.
“Do you??” He sounded angry.
Just then, my cock was starting to pump out cum. He pulled the blindfold off. He stared into my eyes, and I into his. He kept fucking me. I still had this surprised look on my face. Then he took the camera and took pictures of me showing my face, and all while he fucked me. Then a huge load of cum came flying out of my cock and into my face – and kept cumming while he still took pictures. He laughed so hard when the cum hit my face.
“HA-ha. Oh my…great shot, slut. Now put the cum in your mouth and swallow it, slut!”
I did as he asked of me. He kept on fucking me.
“Please stop, Thomas…please!”
I could hear him get even more aroused. “My best friend is a fucking sissy whore! And stealing my mother’s pantyhose…puts them on and licking my mom’s panties too! Eww…fucking filthy sissy!”
I guess he saw everything through the key hole last night while I was in the bathroom.
“I’m so sorry, Thomas. Stop…please!”
He just kept on going fucking my hole. It was so sore by now.
“I knew I should get home from work when I had seen you through the keyhole. I knew you would be doing something naughty!”
He took my pantyhosed-covered feet towards his face and sniffed them. MMMmm…I was feeling my cock come to live again.
“MMmm…Thomas…lick my pantyhose feet would you?”
“No…I will suck them for you!”
He took my pantyhose-covered feet and sucked all over them. I was moaning so much it felt as good as getting fucked in the ass. And I got fucked, and my pantyhose feet sucked.
He held my feet with one hand and took some more pictures with the camera. He was taking selfies with my feet in his mouth.
“I am going to cum, Thomas!!”
I could feel his cock in my ass starting to pump. He then pulled his cock out, and right then, I came on myself – not enough f***e to hit my face, but it went up my stomach and his mom’s bra. He took of the condom and jerked himself off in front of my face.
“Open your mouth, bitch!”
“No Thomas…I’m not going to eat your cum!”
He slapped me hard across my face. “You are a useless little sissy whore that took my mom’s pantyhose and clothes for your own perversion! Now take your punishment like a good little girl!”
I opened my mouth.
“Good Sissy!”
He jerked off faster and faster. I heard him moaning harder and harder.
“You ready, bitch?!”
I did not even get the chance to answer when I felt his hot cum went in. Oh my, did he cum a lot! He was staring intensely into my eyes, and I look at him while he was filling my mouth with cum. He was so getting off of this.
“Shallow it, sissy!”
I really tried to, but I did not like the taste of it! As I kept trying, he was tying my feet up again. I panicked and spilt some of the cum and swallowed the rest. “Eww. What are you doing??”
He saw I had spilt something. He did not answer and kept on tying the other foot down. When he was done tying me up again, he came over and slapped me again.
“Sorry, Thomas!”
He looked at the cum I spilt on my shoulder, looked back at me and said “That not a good girl!” He picked up the cum with his finger, and stuck it in my mouth. “There you go, bitch!”
I swallowed the rest. He then put the blindfold back on.
“Please Thomas, let me out!”
“I am going back to work. Now listen…if you say anything to my mom about this, then these pictures will get out somehow! All of the cum and torn pantyhose? It’s not my problem…it’s yours! You’re gonna find on something to say to her…as long she doesn’t know I was here! You get that, Sissy boy?!”
And now I was back to scared again. “Yes Thomas!” I could feel the tears come again.
“And by the way, you ain’t going to come to my house anymore after this…or I will tell on you!”
Now I just wait again. I just wanna go home.
My Friends House Part 6
After I heard him leave, I started to try to get out somehow, but I had no strength left after all of this. I was so tired that I fell asl**p again.
I don’t know for how long I slept, but I woke up in pain.
She whipped me across my feet, and the fear kicked in again. Was this my so-called friend again, or his mom? Either way, I’m in for it again.
“Who is there?”
I got one over my feet again. It hurt pretty much, but then the aroused feeling came back.
“MMMmmm!”
I got one more – and it felt so needed for my pantyhose feet! I could hear her or him, doing something in the closet – like something got opened and closed again. Then I heard the person starting a computer up in the living room. You know the Windows start-up sound!? Anyway, I heard something in the kitchen that sounded like the person had gotten some coffee or tea. For the next few minutes I heard nothing. I was freaking out again. What was going to happen? Then I heard someone moaning, like the person was watching porn on the computer. I had no clue what went on! Then I heard the volume go up.
And the moaning got even higher! I was getting a bit turned on to! And could feel my cock rising in the pantyhose, covered of my own cum. Then I heard a girl start moaning – and that was not the computer! She actually screamed and moaned at the same time. It must be his mom!
I got even harder, knowing that I’m in her clothes, covered in cum, and laying in her bed while she plays with herself whilst watching porn. I heard someone talking…
“You better behave yourself, or maybe those pictures will be used against you!”
I totally freaked out and knew I was done. I was done as a man; everyone would know I love being a crossdresser! She had fucking filmed me while she was gone. Oh my god! I started bursting into tears – I don’t think she heard me. The movie was still going, and she still played with herself. Getting louder.
“Little sissy is getting rock hard I see! Let me take a picture of that cum-covered sissy cock!”
I heard some laughter too! Oh I wish I was someplace else!
“My best friend is a fucking sissy whore! And stealing my mother’s pantyhose, puts them on, and licking my mom’s panties too. Eww…fucking filthy sissy!”
I heard her laughing even louder. It was so fucking embarrassing.
“You are a useless little sissy whore that took my mom’s pantyhose and clothes for your own perversion! Now take your punishment like a good little girl!”
I heard his mom moaning out “Good, son. Give that little cunt her punishment!”
I could not believe my own ears. Are they in on this together? I was pretty much in a state of shock. Am I even gonna get out of this?
“I am going back to work. Now listen…if you say anything to my mom about this, then these pictures will get out somehow! All of the cum and torn pantyhose? It’s not my problem…it’s yours! You’re gonna think of something to say to her…as long she doesn’t know I was here! You get that, Sissy boy?!”
I heard the part about me and my friend was getting to an end. What was she going to do now that she knew? I heard her climax! Wow! I’d never heard a woman moan like that! I have watched a lot of porn, but it was such a different thing hearing her! Knowing that his mom saw her own son fuck me brutally in her pantyhose turned me on like hell! I heard her doing something with the computer, and then I heard footsteps coming towards the room I’m lying in. She came in and sat down on my face with her pussy. But she still had her pantyhose on, and they were all wet from her squirting her juices.
“Drink up, sissy…and listen to me!”
I was scared of what she was going to say about her son fucking his sissy friend in her own clothes!
“I see that my son likes you very much! Do you like the attention he gives to your sissy body?”
My whole body was twitching. Oh I loved when she talked to me like that!
“Yes, Mistress!”
She was still sitting on my face with her wet pantyhosed pussy, and me still trying to clean her cunt! I loved the taste of her wet juices, and the odour was sweet.
“Good whore! Now I’m going to teach you and my son a lesson for behaving badly!”
I could feel her get out of the bed. With her juices still running down my face, she stood up and I heard some noise that I had no clue what it was! It got all quiet.
“What is your name?”
Why did she want to know that? She already knew who I was!
“You know that, Mistress!”
I got whipped over my feet.
“AAAhhhh!” Mmmm…it felt so good on my pantyhose feet.
“Say it, whore!”
I got one more. Mmmm! The sensation in my hosed feet was amazing! I started to wiggle them and arch them – I could not hold my sissy feet still.
“My name is Martin, Mistress!”
And I got hit once more. My cock was getting aroused.
“What?! More than Martin! Answer!!”
Right then, she took my blindfold off.
“Snow. Martin Snow, Mistress!”
The light in the room was so bright; I could not see a thing at first. But then I saw her face. Oh my, she was so pretty! Those lips, with a dark red lipstick with a lot of shine to them. And her big smoky eyes, just staring into my face. She wore some black Wolford pantyhose, a black pencil skirt, and a red shirt, and some very high red velvet heels. Amazing!
Then I saw the video camera she held in front of my face.
“You’re a good sissy, Martin Snow. Now what is your sissy name?”
She filmed me all over. My cum-covered pantyhose cock, and my pantyhose feet. My body was shaking so much just from sheer excitement. My urges became too strong and I gave in for my sexual desires. I looked right at the camera and said “My name is Jennifer, Mistress!”
I was feeling so sexy.
“We are gonna make a little film, Jennifer…for my son! But first we need to clean you up!”
She untied me. I looked at the clock on the wall and it was 2 in the night. She kept on filming me sitting at the edge of the bed all ‘used’ in her clothing.
It felt so sexy getting filmed. I did not give it a thought what she was gonna use it for, but in my sheer excitement, I did not care.
“Now Jennifer, you are going to take a shower with the clothes on at first!”
I did as she ordered. I went to the bathroom and stepped up into the bathtub, and took the shower head and turned the water on. I could feel my feet getting wet in the pantyhose I had on. It felt and looked amazing.
“Now wash yourself good, Jennifer, you little sissy girl!”
MMmmm! I got turned on and could feel my cock rising. She now had put the camera down on the sink table so she got a good view of it all. She came over to me and took her skirt off. That was eye candy for sure! My cock got real hard by now. She looked me in the eyes while she unbuttoned her shirt and took it off in front of me.
“Jennifer, did you like getting fucked by my son? Used like the little sissy doll you are?”
I didn’t really listen to what she said to me. I just stared at the woman in front of me. My friend’s mom, in Wolford black pantyhose, with a black thong and a bra to match, and those red velvet high heels. She looked at me with an angry look upon her face.
The next thing I knew, I got hit so hard in my balls, I fell down into the bathtub.
“You better listen when I talk to you! I see you missed a spot on your cock and your mouth!? I’ll better give you a hand!”
She turned off the water, and started to take her high heels off. Those pretty, big feet, all covered in nylons, with a dark red colour nail polish. I was so focused on her feet; I just wanted to taste them again so badly. She then stood up on the edge of the bathtub with her feet on either side and spread her legs open. The view I had was amazing! Seeing her thong surrounding her holy pussy, and the pantyhose on top, encasing her legs to elegance. I took my hand up to her feet and felt them all over. I would do anything she wanted to with those nylon feet of hers!
“This is what you get for getting my son to like sissy girls!” And she started peeing on my cock. It felt amazing feeling her warm pee on me – and must have looked sexy as hell. “You like it when mommy pees on Jennifer?” She laughed out loud, like a little evil sounding, just got me turned on even more.
“Yes, Mistress!”
I was moaning so hard right now. She turned to look at the camera…
“Now son…I caught you doing some fucking with this little whore of yours…and this little sissy is taking and purring on mommy’s clothes for you and he to enjoy! Giving in for some sissy cock and pantyhose feet? I thought my son was stronger than that! So I need to punish you both!” She turned her eyes on me again and peed in my face. “Open that sissy mouth of yours, Jennifer!”
I had closed my eyes and opened my mouth as much as I could. She kept on peeing, and the taste of her urine in my mouth turned me on so much.
“Swallow, Jennifer…drink my piss, you filthy little useless doll!”
MMMmmm…yes, I loved this! I tried to swallow it, but I couldn’t. I got slapped across my face…
“That’s not a good sissy. Bad Jennifer!”
I got slapped again. I could feel my face getting warm after the slaps.
“You better drink it this time. You wanna show your boyfriend that you’re a good, obeying sissy, right?”
“Yes, Mistress! I’m very sorry…it will not happen again!”
She filled my mouth again and f***ed me to swallow it.
I’d never tasted anything like that before; very salty, but with a sweet taste at the end.
“Good girl! Maybe there is hope for you after all! See, son…he can be a good sissy girl!”
I was horny, I played along. I looked at the camera to say “Yes Thomas, I can be a good girl!” I said with a horny sissy voice and moaning. I was still lying in the bathtub in her clothes, with her sweet pee all over me. She sat down in the bathtub with me, at my feet side, and pointing her nylon pantyhose feet all covered in her own piss.
“Suck the pee out of my nylon feet!” She said with the camera in her hands.
It did not take me long to take her feet into my mouth. “Oh, my Mistress, I love sucking your hosed feet and the piss. MMmm!”
“Good girl…keep going! And if you clean them good enough, you can take them home with you!”
I sucked on those nylon feet with all I had. After 5 minutes, she stood up, went to get her phone, and called someone.
“Hi Thomas, it’s mommy here!” She held a finger on the mic. and slapped me. “Keep sucking my feet, Jennifer! Do you want these pantyhose or not?”
“Yes Mistress…I really want them so bad!”
“Mom?? Hello, Mom? You there?”
“Yes son, I’m here. I’m lying in the bathtub taking a bubble bath. Well see you tomorrow then, hunny!”
“Ok Mom, bye!”
I started to moan louder when she hung up the phone.
“Ohh yess, Mistress…you make me so fucking horny! You are going to make me cum!”
She filmed me with one hand and started to jerk me off with the other. It felt great, feeling her fingers caressing my pantyhose cock.
“I am going to cum, Mistress!”
“Good sissy…cum over mommy’s feet with that little excuse for a cock!” She pointed her amazing-looking nylon feet near my sissy cock. “Let’s see what that little cock has got inside of it. But it can’t be much! He-he!”
Just then, I came so hard over her nylon feet. The warm cum all over her toes. I took her feet in my mouth and sucked all of my cum of her pretty nylon feet.
“Good, Jennifer! You think you’re ready to be my son’s sissy girlfriend?”
With all the cum in my mouth, I looked at the camera intensely. I swallowed and licked my own lips.
“Yes, Mistress!” and she turned the camera off.
“That’s good for now, sissy. Now wash yourself good and throw the dirty clothes in the laundry basket. Oh yea, here is your pantyhose!” She took them off in front of me and threw them into the shower with me. “After you’re done here, come into my room!”
My Friends House Part 7
I kept on shaving my stretched leg like a real sissy would. “For my boyfriend, Mistress!” I was biting my lip while I shaved and I think she saw me.
“Uhh…I see you like this very much, little bitch!? The attention your sissy body is getting! We are gonna make you a pretty fuck doll for my son to enjoy!”
She turned the camera around to her own face. “You see, son…how mommy taught this sissy excuse for a friend you’ve got, into a proper girl for you! A real fuck-doll for you to please as you wish!”
She turned the camera around towards me again. I stood there with a surprised look on my face, baffled over what she just told her son. She walked over to me and grabbed my balls.
“YES! Yes, Mistress!”
She walked out of the bathroom. “Hurry up and be done, Jennifer!”
I finished shaving all over my body. I took a towel and went into the bedroom. She had changed the sheet on the bed with like one of those plastic sheets.
I threw the towel on the floor and got smacked on my ass. Wow, it felt good!
“Pick up the towel and hang it beside your pantyhose in the bathroom!”
I picked up the towel. “Sorry, Mistress!”
“You’ve got some pretty cute feet, Jennifer! Some good legs, nice big ass…a little to the chunky side, but even that is sexy on you! I bet other boys love you like a little sissy!”
“I never showed my girly side until you caught me in your clothes, Mistress…and your son who also caught me! I’m not very good at hiding my girly side!”
“What nail polish do you want on? These colours would suit your skin tone!” She showed me 3 colours, and saw one of them look like the one she had one.
“The dark red one, Mistress)
“Good choice! That’s the colour I’ve got on!”
“So what do you think off all this? What has been going through your mind while I treated you this way? You know…like a little whore?!”
She kept on painting my nails.
“Someday we need to take you out! But never think you’re out of the clear! I’ve got it all on tape!” and pointed out the camera behind her.
“Yes, Mistress. I’ll obey every wish, every desire you’ve got. I am your sissy slave!”
“Good girl, Jennifer. And you know you’re my son’s slave too! Though I still need to punish him for falling for his sissy friend!”
“Sorry, Mistress!”
She rolled up one of the stockings and slid it on my foot. Wow, everything felt so erotic!
“Now stretch your leg in the air for me!”
I was waving my legs around, and admiring them in those sexy stockings of her – and with my painted nails! It was such a turn on for me.
“Good girl! I see you like being in mommy’s stockings, showing off your pretty amazing looking feet and legs! We need to show them to other men some other time. But we are not done here yet!”
“Turn around for mommy, Jennifer, and stick your ass in the air!”
I did as she ordered.
“Now take your hands and spread your ass for me!”
Again, I did as she said. I heard her spitting and felt it in my ass.
“MMmmm…you shaved yourself real good around your used hole!”
“Sorry, Mistress. It’s just that your son was not even as thick as that plug. And your son really hurt me!”
“You need this, Jennifer! It will be used a lot in the future, and there will always be a bigger cock!” Then she pushed the butt-plug in with all her f***e, but it didn’t go in. The pain was tremendous, and I screamed for real, and started crying.
“Stop being a little girl! Now turn around and stick your feet in the air!”
“Now spread those lovely stocking legs for mommy!”
I spread them out and she tried to f***e the plug inside of me. She used all of her strength to push it in. And then I felt a pop. I let out a big moan. I must have sound like a real bitch! The plug felt sensational in my pussy hole. I stopped crying and waited on what happened next.
Without hesitation, I put them on.
“Wow, Jennifer. You like the daughter I never had! I almost can’t see your tiny cock!”
“I bought you some breast implants to put in your new bra! I bought them quite big, because you’re a little chunky on the side!”
I started to put on the shapewear over my bra, and it really slimmed me down and gave me some curves.
“Yes, Jennifer…I thought you needed a gift…after all you have been through a lot, and being a good girl about it!”
I was so honoured and excited at the same time!
I jumped into the skirt, and it fit perfectly over my bum. Oh, I got some nice looking hips in this skirt! I was posing in front of the mirror. His mom was laughing at me. I did not care a bit. I put the pullover on. And the lace looked amazing on my body! I was feeling so sexy and kept on posing for myself. She filmed me while I posed.
“Yes, Mistress!”
I sat down on a stool and she started applying makeup to my face. My skin looked so smooth after the first layer. She then gave me dark red lips and applied lipgloss. Then she worked on my eyes, making a smoky look with also a red colour to it. To finish it off, she did my lashes, and placed a necklace around my neck. I looked at it – it was a key.
She took out a black wig with curls and put it on me. I was stunned on how good I looked. This entire journey has all been worth it!
“It is a key to my house. So you can go in and out when you want!”
“I do not think your son is going to be happy about that! You saw the tape yourself! He said I should stay away from him and his place!”
“First of all…this is my place, not his. Second…he still needs to know who is in charge around here. That’s why I need you for my plan!”
“Yes, Mistress. Use me like the sissy whore I am!”
“Call me mom. And yes, you will get used a lot!”
“Yes, mom!”
“Now go out in the kitchen and make mommy and yourself a cup of coffee. I’ll just finish up in here, then I’ll come out!”
“Yes, mom…as you wish!”
“Is this girl not beautiful? And she obeys everything mommy says! Right, Jennifer?”
“Yes, mom!”
“Wanna see some tricks, son? Yes, you do! Sit on your knees on the floor and bark like a dog!”
I did as she told me – I sat down and barked.
“Wuf wuf. Rrrrr Wuf!”
“You see how good mommy is? Now stand up and put mommy’s nylon feet in your mouth!”
“Yes, mom!”
I took her feet in front of my mouth and started sucking those amazing white nylon feet.
“You see she can do a lot of tricks! And look how much the little slut likes mom’s nylon feet?!” she filmed me sucking her sweet nylon feet.
“Yes, mom. I love washing them for you! MMMmmm!”
“Now go finish making my cup of coffee, bitch!”
I walked back to the kitchen, and heard her finishing off.
“Now son, you need to be punished for what you have done! So just wait…”
My Friends House Part 8
I sat down and drank my coffee. I could see my lipstick sticking to the cup. I liked that very much. I felt very much like a girl, and I loved it.
“Yes mom. But how are we going to do that? He told me to stay away from him!” I looked at her while she looked at me. I loved the feeling of being ogled over like this.
“I’ve got a plan, but you can’t know, because then the surprise element won’t be there! Just do as mommy tells you to!”
I smiled at her “Yes mom!”
“Go get the paper in the mailbox! Meanwhile, I’m going to start making the video for my son!”
I got all stiff. She wanted me to go get the paper while I’m wearing my new girly outfit.
“You mean outside, mom?”
“Bend over the table, pull up your skirt, and place your hands on the table!”
I knew I should have kept my mouth shut. She walked in to her bedroom and came back with the whip. And she hit my ass 3 times, fast. And then slow once, really hard. I screamed like a sissy girl.
She whipped my ass one last time.
“Arghh! Yes mommy! Yes Mom!”
I pulled up my skirt even more, to reveal my ass all covered with whip marks. I rearranged my thong. And then I heard something drop behind me. I turned around and saw this boy staring at me. I quickly pulled my skirt down, smiled at him and walked towards him. I felt like I was going in slow motion. His eyes were focused on me, looking up and down my body. My booty was shaking from side to side while I walked. I bent over so he could see my nicely formed ass. As I did so, the skirt went just above the stockings. I could feel his eyes staring at me. I picked up the newspaper, and stood up.
“MMMmm…you liked that Jennifer! I saw you through the window!”
“Oh mom, that turned me on so fucking much!”
“Good girl! I see that you found a pair of my shoes? You like them, bitch?”
“Yes, I love them, mom. They feel so good to wear on my stockings feet!”
She smiled “You can keep ‘em, Jennifer. They look very pretty on you!”
“Sit down and relax, Jennifer. I need to finish this before my son gets home!”
She came closer without showing herself to him.
“Is that your teacher??? Sure looks like him!”
I smacked myself. My ass hurt so much after she whipped me. Then I heard him…
I could hear him through the TV. Yes, that turned me on so freaking much.
“Good thing I came back to spy. I love little sissy girls, OOHH Yes! Look at that body!”
“Is that an invite, little bitch? MMMmm…I wanna fuck you, sissy whore!”
I pulled up my skirt to reveal my whipping marks. I smacked myself again, and moaned out loudly.
“Now look at that little sissy girl…she has been a bad little whore!”
“Oh baby…you need a proper fucking!”
I heard mom whisper “His cock is big. And he wants his sissy whore now! Should I let him?”
I nodded discreetly.
I pushed away the thong from my hole. Now he clearly saw the diamond in my ass.
I saw his big cock on TV. He stroked it hard and was all wet from his own spit. I was on all 4’s on the coffee table, and sticking my ass out for him to enjoy.
I turned off the TV. He then put on a black mask and sneaked inside the house. I still pretended I did not see him. Right there, he pulled me back and hold tight on to me.
He slapped my ass and tried to stick his cock in me.
He was too big for my little hole. I screamed and started crying.
From behind he stuck 2 fingers deep in my mouth. I gagged on his fingers. He then took out his fingers and put them in my ass.
“Arghh! Ouch!”
“Oh baby! You’re so god damn fine! Showing off that little sissy cock. You’re a really bad girl!”
Now he just f***ed his way inside of me. I felt his tip on my hole, without a condom on. I was so freaking scared and it hurt.
“Now you’re gonna like my cock in your ass. Like a real filthy slut!”
I felt his tip enter my ass.
The next thing I knew he was inside of me with the giant cock of his.
“AAAHHH!! Yess…you felt that, whore! I see how you like my cock in your pussy hole!”
I moaned so hard and he just kept pounding my ass with his big cock.
I could feel his cock in me pumping so hard. With every stroke he took, the closer I got to orgasm.
“MMMmmm, Sir. Why are you pulling out of me? It felt so nice!”
He turned me around so that I was lying on my back. He turned me around like a little doll.
My mascara was running down my face with all of that crying. He just went right inside of me…
I looked at him while he fucked me hard. I felt like the time went slow. I could see him standing there in his mask, just pounding his big cock back and forth. Me, getting fucked by my own teacher! I saw mom in the window, standing there in her white stockings and see-through bathrobe, holding the camera and filming me. I was turned on by this so much. I was just embracing the fucking I was getting.
I moaned like hell.
While he was inside me, he took one leg up beside his head. Sniffed my leg, and took my shoe off.
“Wow, you have outdone yourself for me! Look at those amazing red coloured nylon toes you have!”
He was inhaling my nylon feet, f***ed my toes in between his nose, and sniffed real good.
He opened his mouth and sucked my nylon toes. I felt so magical with a cock inside my pussy and my nylon feet getting sucked. I looked out and saw mom slowly enter the living room, through the window door I had left open.
“Oh yes, Sir! I love it!”
“Let me help my little bitch cum on her own amazing looking stocking-clad legs and feet!”
He tightened his grip around my ankles.
“Please don’t cum inside me, sir!”
Mom moved behind him.
Mom just stood there pointing the camera at me like nothing happened. I felt something warm deep in my ass. He’d cum inside me with great f***e, and let out this big grunt of a sound. The same sound I heard outside when he peeked on me. He was still filling my ass with cum and released his grip from my ankles and kissed my feet gently. He was done.
I was still rock hard, when he pulled his cock out of my hole. Then mom just ripped his mask off his face. He fell down on the ground in front of her. I felt the cum inside me slipping out my hole and on to the table.
Mom filmed the mess on the table. “That’s not your fault, Jennifer. This bad bad man did it…and he is going to clean up. Are you not?”
“What the hell is going on here?”
As he lay down on the ground, Mom kicked him right in the balls. He just rolled up to a little ball. He felt that one.
He started to get some air again after his hit.
“Where you know my name from?”
“That does not matter for now! Why did you just go inside my home?”
“Look, I could not help myself. My urge was too big…seeing a little sissy girl like that! She was teasing me!”
“I know she can be a really bad girl. But she is learning! It still doesn’t give you the right to go into my home! So you gonna clean up your mess you made inside Jennifer!”
“Jennifer, we need the table clean first. Stick your feet in his cum and let him lick your nylon feet clean!”
“No…I don’t eat cum!”
“You know I got the whole of this filmed. While you were outside hiding, and in here fucking this pretty sissy girl. You are one really bad man, Johnny. Now suck those cum-covered nylon feet!”
I was loving this.
Mom was in control of everything, Wow…mom was so fucking hot.
“I can’t! Please let me go!”
Mom kicked him in his stomach. “You better do as I tell you. You are worth nothing to me! This film will get out if I hear anything about this!”
“Oh my god. I love this feeling, mommy. I feel like a real girl”
“You are, sweety. You attract men. If that’s not what a real girl does, I don’t know what is!”
“I’m going to cum soon, Mommy!”
My body was twitching; it felt amazing fucking Johnny’s head.
“Johnny!” His eyes turned to mine. (It is me, Martin Snow!”
I saw his face get a surprised look. He tried to pull away, then mom pushed his head all over my cock. It felt incredible. I unloaded my cum into his mouth. Mom held his head in place.
“Are you done cumming, Jennifer?”
“MMMmmm…Yess!!! I’m done, mom!”
“Now you better drink every drop of that sweet sissy cum you just got. Not many get that lucky!”
“Martin, I’m so sorry. I did not know it was you! You are not gonna tell about me, are you?”
“Perhaps! Maybe I need you for something later!? Because now, you’re my bitch. Get that?”
“Yes, of course, Jennifer!”
“Jennifer, go take of those cum-covered stockings and clean your feet, your pussy hole, then take the pantyhose on I gave you!”
“Sure thing, mom!”
“Listen…if you hurt that girl in anyway, then I’ll make sure everyone gets to know what you did today! Now get out of my house!”
And hopefully… You will have learned your lesson.
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