u/Firm-Bend6863

So this happened when I was 24. By this time I was already well versed in sissyhood.

I had a collection of outfits, lingerie, wigs. I kept my body shaved when I was able to (mainly in the colder months since I would wear pants more often in my day to day).

While my normal weekdays didn't deviate from my life too bad (mainly some minor dressing and teasing online). The weekends were my playtime.

Normally Friday after work I would go home, get changed into a cute outfit I picked out the night before and spend time solo.

Saturdays were the days I went out. Sometimes it was to a CD friendly gay bar. Those nights normally ended in me blowing a guy in his car or being bent over his truck. Sometimes I went to an ABS after hours. More than a few times I would spend the day on Grindr to arrange some nighttime fun.

There I was still sitting in my boy clothes at like 2pm. Just checking out my profile, seeing who was looking good. Eventually I get chatting with a nice looking guy. Early 40s, BWC (least 7 inches), hairy and tall (I average around 5 '7 in flats, 5' 10 in heels) he was at least 6 '2. (He will be referred to as James going forward)

We start chatting, im being playful by sending him photos and a little teasing. He responds by saying he wants to meet at his place later that night. I agree and show him a few outfits and ask what he wants me to wear. I believe it was between a school girl outfit (blouse, skirt, stockings,heels) a housewife getup ( 50s style dress, leggings, a little more makeup) or a “slut” outfit (miniskirt, fishnets, pumps). He ask for the housewife (my personal favorite). He send me his address (about 15 min away) and we set the arrival for a little after dark around 830.

I start getting everything ready around 6pm. Gives me 2 hours to get decent. I just hop out of the bath when I see a message from James. Asking me if I mind a change. He was going to have a buddy stop by for a bit tonight. His buddy, and him, are on the DL ( I learned after arriving that he was MARRIED with KIDS). He said we can reschedule OR when he arrives I can sneak off to another room since it will only be a few minutes. At this point Im already prepping and horny that I dont want cancel. I agree to hide, IF he knows what time he was going to arrive. He said he was going to arrive around 9 so we will pause then.

Perfect!

By the time I finish everything, I am sliding on my black heels and fixed a perfect red head wig (think a MUCH SMALLER version of PAM from Married with Children). Even added a little bandana to complete the illusion. I wrap a coat around myself and get into my car.

I arrive at a nice little suburban house and I see porch lights. It's 8: 30 and I text him saying I'm outside. He said the door is unlocked to just come in. So after taking a deep breath I walk up and open the door.

THE FUN:

I get there and he greets me at the door. He says I look lovely and I do a little spin and a curtsey.

I put my purse down (filled with lube and condoms in case he wasn't clean) and came over to him. I put my arms around him. Telling him it feels good to come home to a big strong man.

He offers me some wine and I sit on the couch in my best “knees together good girl” position. After taking a few sips I ask him what he wants to do?

He leans over and starts making out on top of me and I am just going with it. I feel him grope my breast (padding) as my hands slowly make thier way down his pants.

Eventually I get to the bulge and it feels so HUGE!. I ask if he wants me to take care of this? He backs off a bit and undoes his belt. I slide to my knees and fish out one of the biggest WHITE dicks ive seen. I make sure my hair isnt in the way. Give it few tugs and a lick for good measure. I do my best to take it as deep as possible and I see his head lean back and his hand goes on my head. I take that as my sign he likes it.

I am about 10 min in and was gonna end it soon (i came for this in my ass) then…We both shoot up as we hear the door. We lost track of time and when we looked at the clock it was 9:10. In walks his buddy (“Mark)”. About as tall as him, little darker skin, not bad looking.

He came in saying “Hey man, sorry im late, I just wanted to see if you had…” There was at leas 15 seconds of silence as I sit there with James’ cock in my hand. He starts laughing asking if he was interrupting. James plays it off saying that I was just a sissy (clearly not his first). Then he does something that would normally be a turn off, but I went with it.

“ You want a go at her?”

There he was, a man I just met offering me up. I should of been mad…but I was just turned on. I let go of James and put my knees together and in my best femme voice “Id be happy to help you”

Mark gets over to me and slides his pants down. His cock is roughly the same size of James and,unlike him, not as gentle. As soon as the pants are off he guides me to his cock and I swallow it like I'm expected to. I spend a good 5 mins getting throat fucked, All while James is jacking off.

James gets up and starts pawing my ass a bit. I extend it out to let him and he ask if im ok with sharing. I nod and Mark lets me breath.

I get my arms up on the couch and extend my ass. I tell them there is lube in my purse. Before I know it, the shirts are off and I have 2 naked men in front of me. James lubes himself and is generous. I slide off my black thong and he applies it to me. At this point I'm all in “Yes daddy, I need your married cock inside me!”

Suddenly he enters me and after a few seconds to adjust, starts going hard. I start moaning, all while my cage is clicking against me. Mark gets on the couch and places his dick right in front of me. I go off instinct and take it.

“Let me see those titties!” He undoes the buttons on the top of my dress to expose my bra, rips of my bandana on my hair, all while I'm getting railed.

I'm lost the moment I don't look at his face. I did not see him take his phone out. He starts recording it.

They are both laughing, im getting some light smacks on my ass and face and start talking dirty.

“Whos our good little girl?” “I am! I am daddy, fuck your little girl!!!”

They both pull out and guide me back on my knees. THey start jerking it in front of me and I know what to do. I open my mouth and start begging for it. Before I know it 2 hot loads of thick cum are draping down my face and clothes.

When they finish I jerk them both a bit for good measure as they sit on the couch. After a little rest, I get my shoes, bandana and purse. I tell them I need my beauty sleep and I had a lot of fun. James gets up and walks me to the door. He said he feels stupid for not checking the time. I tell him it was fine and I had fun. Mark ask if he can have my number for the future. I agree and sign it Jenny with a little heart.

I tell them both I had fun and would love to repeat this.

I button my top up a bit and walk to my car.

When I get home I basically pass out as soon I get to my bed, still in my dress covered in cum.

Only after did I remember the video. I decide its not worth making a snuff over since no one knows who I am. But its probably still out there. Maybe online? Shared between his friends? I never did see them again so who knows.

Fun to think one day my wife (married years later) may find it lol

People seem to really enjoy when I post these stories from my youth so I figured it was worth another one.

This one is about my last weekend in college before graduation.

I turned 21 in the spring so I was able to finally go to bars and by this point I had a decent group of friends. The important one was a guy named Mark, who when he cross-dressed, went by the alias Tiff.

By this point in my life I was really into cross-dressing, honestly loved doing it, and so did he. Sometimes we would fool around, we banged each other on more than one occasion, sometimes both as Sissy's, but this weekend he invited me out to an event at a local gay bar, about 20 minutes from town.

Didn't feel like doing the dress up, simply because I intended on getting drunk and didn't want to have to deal with all the extra work. He went in this beautiful pin-up swimsuit with his hair and face done and I have to say he looked hot

Fast forward to the night and I pick him (her) up and he directs me to the bar. We get there and it's pretty popping. Some people are all dressed up, some people are just in tight clothing, and some people are just wearing normal clothes. He levels with me and says he wants to have one more native fun before we graduate and I said I'm looking for the same but not with him LOL.

We get to the bar around 8:30 and she instantly goes to talk to some other crossdressers that she knew. Oh well I went to go get drinks.

Throughout the night we hung out, but as he was definitely motivated by his own goals, I kind of spread out throughout the room trying to find someone. That is when I met Dave

Dave was at least in his mid-40s the chemistry was instantly there.. there was some flirting, some fun comments he made about my ass (I have a very small frame and I'm very bottom heavy) after a few drinks and some like touching he invites me to come back with him. I tell him I have to check with my friend and to give me 5 minutes.

I go when I talk to Tiff and she said she was actually going to get a ride home with a few of the girls she was talking to so I can go have fun.

I follow him to his town home about 10 minutes away and he invites me in for a small drink. At that point I knew what was going to happen.

I sat on the couch and he comes out with a beer and wraps his arm over my shoulder, I lean in and before I know it we're making out.

I joke and I say " this is fun, but I'm looking for an entree not an appetizer". He laughs and doesn't stop me from trying to take off his t-shirt.

My God the man was chiseled. Not like a six pack or anything but definitely really toned and from what I could feel very well endowed.

He gets on top of me and we're making out while I'm laying down and I feel my hand go towards his crotch. Decide that I had it of teasing and I start rubbing it vigorously till he gets the hint and starts sliding down his boxers.

I could tell from the silhouette he was huge but my God. He was at least 8 in and extremely thick. I asked him about. He wants me to take care of it and he nods and I started blowing him on the ground while he sits.

He starts moaning and grabbing my head, with a few playful slaps to my face which I was totally fine with. I pop off and ask him if he wants to take this any further his response. " Aren't you a little slut"

Then takes me upstairs to his bed room and throws me on the bed. I take the opportunity to take off my clothes and get nothing but in my boxers till he decides to rip them off and starts playing with me. I was so aroused I would have done anything at that point. He grabs his dick and says do you want it? I say yes please. Daddy and he tells me to bend over.

I get on all fours, here. I am on all fours on a bed of a man. I just met less than 2 hours ago and I am waiting for it. He goes to the dresser to get lube. I hear it putting in on him and I feel cold coming on my hole. I shake my ass and anticipation, he slaps it and then shoves it in hard.

Instantly. I'm an ecstasy. I moan hard and I could tell he likes that. He grabs my hips with both hands and starts thrusting. I'm sitting there on all fours getting destroyed and I love it. Eventually he flips me over and starts missionary, all while I'm jacking myself off.

Finally, he starts talking dirty. Calling me a slut, whore, telling me to beg and I beg hard. I'm pretty sure his neighbors might have heard from how loud I was being.

I can tell he's getting close and I ask him where he wants to finish and he asked for my face.

He pops off. I get on the ground again and he starts jacking off while I'm basically licking his shaft. He nuts hard and before I know it I have four to five globs of white hot man juice on my face. He then decides to do me a favor and pretty much sits on top of me to jack me off telling me to beg to finish.

Finish and now I'm covered on my stomach and on my face. He said that was a lot of fun, I agreed. He asked if we wanted to meet up again and I told him I'm actually moving back home next week cuz I'm a senior. He understood.

He asked if I wanted to stay the night or at least grab another drink. I said no because want to make sure my friend got home okay..

I clean my stomach up and decide just to leave the face because no one's going to see me at like 10:00 at night.

Get back to my dorm (solo dorm which was a huge plus). And I start texting Tiff. She said she was wondering if I was okay and said that her and her girlfriends just decided to stay at her place and have a few drinks and she was getting ready for bed. She asked how my night went.

I decided to send her a picture of my c**-filled face as a response.

She still has that photo as my contact to this day

This story takes place when I was 21, fresh out of college. I graduated in May and moved back home until I found a job and could get my own place. 

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After I long day of working outside I get back to my room, I go on Grindr. I update my picture to me being on all fours, ass in the air. I also add some of my tongue out (think panting) as well as some of me in favorite outfit (its a classic 50s housewife dress with stocking, my blonde wig down to my shoulders, makeup and classic heels). 

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I remember posting something along the lines of “Little fairy boy needs a big man to teach him a lesson”

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I let the post go and go take a nice long shower and shave. I get back 15 minutes later and i am flooded with messages. After going through a few boring ones, I found a jackpot. 

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He was Spanish, mid 40s, 6ft, Big Hairy Chest. He had a much larger frame than me and had a stern look on his face.

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He said he was home alone and could use the company. After sending pictures back and forth, he said he was looking for a sissy boy to entertain him. I asked him how he wanted me to dress and gave him some options. He requested to look at the picture. 

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I told him I could do that BUT I would need to arrive in boy mode since I can't get THAT dressed at home, he agreed. I packed what I needed in my bag, told my parents I was going to chill with some friends and that I might spend the night. Grabbed my keys and left.

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I drove for about 15 minutes and arrived at a small townhome community. I take a look in the mirror, get my nerves together and go to his unit. I text him that I'm outside and he opens the door. 

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He is wearing boxers and a tshirt and i can feel myself getting hard just looking at him. We say hi and he walks me in. After a few minutes of small talk I ask where I can get ready. He shows me to the guest room, taking ample time to grope me as we walk upstairs. As he walks in me i make sure to tell him itll be worth the wait as I grab his crotch and play with him a bit. I stop, blow a kiss and close the door.

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In the guest room as a nice vanity and a chair, I emptied my bag and laid out my clothes: A nice blue 50s housewife dress, heels, stocking, my makeup, Nice white pushup bra and no panties.

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I try not to get lost in it dressing up (knowing I have to entertain and after 20 min i get a text asking if im alright). I sent him a selfie of me with my makeup and wig on saying ill be down in a min. 10 min later I go down the stairs in my full outfit and he is just sitting on the couch drinking a beer. 

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I ask if he is going to offer it to a lady. He gets up, I give a little twirl and he grabs my ass and pulls me in. He offers me a drink and puts it down in my best , legs together, pose and take a swig. I tell him its good but I want something else to put in my mouth. I slowly get down on my knees and fish his cock out. This thing is HUGE, at least 8inches thick. I feel like a lucky sissy and start just enjoying myself. He leans back, switching between watching tv, drinking and putting his hand on my head. We are great until he gets a text. He asks if he can send his buddy a pic and I agree. He gets on my blowing him, of me sucking his balls and kissing his cock.

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After he sends it I keep going and he ask a question I was not expecting: “My buddy wants to know if he can swing by.”

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Now i dont know if it was just my hormones or the moment, but I said yes. 5 min later i go to the bathroom to fix my smeared makeup and I'm told his buddy is pulling in. I get on the couch in my best girly pose and tell him ill wait. 

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His buddy is a spitting image of him, Spanish, BIG, hairy  and just as intimidating. I get up to greet him and tell him my name is “Cherry.”

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He starts pawing at me and I tell the boys to sit down. Fast forward and I am on my knees switching between 2 big cocks. Eventually one guy gets up and gets behind me. I tease a little by lifting my ass and shaking it around for him. He says he is clean and ask if I am. I pop my head off his friend’s cock and say yes sir.

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He lifts my skirt and spanks my bare ass. I jump a little and tell him there is lube in my bag. He pulls it out and I feel the cold gel hitting my hole. I get distracted and his friend grabs my head and helps me focus.

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As he enters me I basically scream onto the cock in my mouth. After a few minutes, he starts moving and OMG he feels AMAZING. Its hitting every spot that I have to stop sucking just to moan. I look back and him “Give it to me sir!” 

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His friend stands up and lifts my head and forces himself down my throat.  My makeup is smearing, my dress is getting ruffled and I am in ecstasy. He tells me he is close and I tell him to finish where he wants and he does it on my back. He looks at his buddy and says “You want a shot?” His buddy gets my mouth off him and gets behind me while they switch places and before I can say anything hes already inside and his friend is tonguefucking me.

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(Its worth noting that nothing is hotter for me than when a man just does what he want with me. Gives me no “choice” and just uses me.)

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Before I know it I'm getting railed hard again, jerking off his buddy. Meanwhile they are calling me names “fairy” “slut” Whore” “sissy” “bitch” and my favorite “cunt”

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They both are about to finish and I tell them to finish on me face. 

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They get my to turn around, I sit with my legs together upright and open my mouth and close my eyes. 

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I feel the white hot cum drip down my cheeks as I say “ thank you sirs”. I Jack them off a bit then his buddy leaves.

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He ask if I wanna stay, I say I can't but I def wanna do this again. He and I exchange real numbers and I put my name as Cherry.

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It's like 12am so I go to the restroom z slide off my clothes and throw on my sweats and hoodie I brought.

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H gropes my ass as he shows me our and I, for good measure (and still with.lipstick on) stick my tongue down his throat and  go home

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I get home close to 1, sneak to my bathroom to clean my makeup off. Pass out satisfied and full of dick.

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This story takes place when I was 21, fresh out of college. I graduated in May and moved back home until I found a job and could get my own place.

​

After I long day of working outside I get back to my room, I go on Grindr. I update my picture to me being on all fours, ass in the air. I also add some of my tongue out (think panting) as well as some of me in favorite outfit (its a classic 50s housewife dress with stocking, my blonde wig down to my shoulders, makeup and classic heels).

​

I remember posting something along the lines of “Little fairy boy needs a big man to teach him a lesson”

​

I let the post go and go take a nice long shower and shave. I get back 15 minutes later and i am flooded with messages. After going through a few boring ones, I found a jackpot.

​

He was Spanish, mid 40s, 6ft, Big Hairy Chest. He had a much larger frame than me and had a stern look on his face.

​

He said he was home alone and could use the company. After sending pictures back and forth, he said he was looking for a sissy boy to entertain him. I asked him how he wanted me to dress and gave him some options. He requested to look at the picture.

​

I told him I could do that BUT I would need to arrive in boy mode since I can't get THAT dressed at home, he agreed. I packed what I needed in my bag, told my parents I was going to chill with some friends and that I might spend the night. Grabbed my keys and left.

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I drove for about 15 minutes and arrived at a small townhome community. I take a look in the mirror, get my nerves together and go to his unit. I text him that I'm outside and he opens the door.

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He is wearing boxers and a tshirt and i can feel myself getting hard just looking at him. We say hi and he walks me in. After a few minutes of small talk I ask where I can get ready. He shows me to the guest room, taking ample time to grope me as we walk upstairs. As he walks in me i make sure to tell him itll be worth the wait as I grab his crotch and play with him a bit. I stop, blow a kiss and close the door.

​

In the guest room as a nice vanity and a chair, I emptied my bag and laid out my clothes: A nice blue 50s housewife dress, heels, stocking, my makeup, Nice white pushup bra and no panties.

​

I try not to get lost in it dressing up (knowing I have to entertain and after 20 min i get a text asking if im alright). I sent him a selfie of me with my makeup and wig on saying ill be down in a min. 10 min later I go down the stairs in my full outfit and he is just sitting on the couch drinking a beer.

​

I ask if he is going to offer it to a lady. He gets up, I give a little twirl and he grabs my ass and pulls me in. He offers me a drink and puts it down in my best , legs together, pose and take a swig. I tell him its good but I want something else to put in my mouth. I slowly get down on my knees and fish his cock out. This thing is HUGE, at least 8inches thick. I feel like a lucky sissy and start just enjoying myself. He leans back, switching between watching tv, drinking and putting his hand on my head. We are great until he gets a text. He asks if he can send his buddy a pic and I agree. He gets on my blowing him, of me sucking his balls and kissing his cock.

​

After he sends it I keep going and he ask a question I was not expecting: “My buddy wants to know if he can swing by.”

​

Now i dont know if it was just my hormones or the moment, but I said yes. 5 min later i go to the bathroom to fix my smeared makeup and I'm told his buddy is pulling in. I get on the couch in my best girly pose and tell him ill wait.

​

His buddy is a spitting image of him, Spanish, BIG, hairy and just as intimidating. I get up to greet him and tell him my name is “Cherry.”

​

He starts pawing at me and I tell the boys to sit down. Fast forward and I am on my knees switching between 2 big cocks. Eventually one guy gets up and gets behind me. I tease a little by lifting my ass and shaking it around for him. He says he is clean and ask if I am. I pop my head off his friend’s cock and say yes sir.

​

He lifts my skirt and spanks my bare ass. I jump a little and tell him there is lube in my bag. He pulls it out and I feel the cold gel hitting my hole. I get distracted and his friend grabs my head and helps me focus.

​

As he enters me I basically scream onto the cock in my mouth. After a few minutes, he starts moving and OMG he feels AMAZING. Its hitting every spot that I have to stop sucking just to moan. I look back and him “Give it to me sir!”

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His friend stands up and lifts my head and forces himself down my throat. My makeup is smearing, my dress is getting ruffled and I am in ecstasy. He tells me he is close and I tell him to finish where he wants and he does it on my back. He looks at his buddy and says “You want a shot?” His buddy gets my mouth off him and gets behind me while they switch places and before I can say anything hes already inside and his friend is tonguefucking me.

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(Its worth noting that nothing is hotter for me than when a man just does what he want with me. Gives me no “choice” and just uses me.)

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Before I know it I'm getting railed hard again, jerking off his buddy. Meanwhile they are calling me names “fairy” “slut” Whore” “sissy” “bitch” and my favorite “cunt”

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They both are about to finish and I tell them to finish on me face.

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They get my to turn around, I sit with my legs together upright and open my mouth and close my eyes.

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I feel the white hot cum drip down my cheeks as I say “ thank you sirs”. I Jack them off a bit then his buddy leaves.

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He ask if I wanna stay, I say I can't but I def wanna do this again. He and I exchange real numbers and I put my name as Cherry.

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It's like 12am so I go to the restroom z slide off my clothes and throw on my sweats and hoodie I brought.

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H gropes my ass as he shows me our and I, for good measure (and still with.lipstick on) stick my tongue down his throat and go home

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I get home close to 1, sneak to my bathroom to clean my makeup off. Pass out satisfied and full of dick.

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Well to be honest here, most of us sissies are hungry little holes and love calling them. Daddy.

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So I want to know what's something you done as a sissy to make your real daddy proud?

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I'll start

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" Daddy when I was 19 years old you volunteered me to help your friend Robert build his deck with him and his 24-year-old son.

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Being around two very strong burly man, glistening in the heat, made me so horny. That as soon as I got back to school, I went on Grindr.

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Within an hour I was doled up like a school girl getting pounded by a 43-year-old man in his marital bedroom, covered in sweat with my makeup running down my cheeks.

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As he went to go to the bathroom and I had laid there in a skirt, blouse, blonde wig, with his seed and my hole and on my face. I just thought to myself you'd be so proud of the man I was"

Ok so this story was about 14 years ago so bare with me on the details (im going based on my best memory).

Year was 2012 and I just turned 19 earlier that year. I was still in college but was home during the summer. It was just my mom, my 2 sisters (1 older in college) and me. Now I knew I was bi for a long time. I dated girls in HS but only started experimenting with men after I went away to school..

Ive explored a bit, everything from making out at a party to having a guy rail me in his dorm room./I found out I LOVE CROSSDRESSING, but its not needed for me to have fun. I even got daring and bought a “big black friend” from a local adult store.

During this time i discovered 3 things about me: I like men, but PREFER women for more serious stuff, I am a bottom…and I am a slut when I am.

Now the story:

My mom was planning a few days down at the shore with my sisters a few hours away. I HATE the beach and get bored easily so I made a deal with her. I stay, house sit, feed the cats AND in turn I can stay. I was excited for some alone time.

I waited a few hours till they were long gone and thought about how I was gonna spend my week. Was I going to go to a gay club nearby? The ABS? Tease some old men online? NAH.

My first move was to raid my mom and older sister outfits for some fun solo time. I get in the shower and shave my body smooth (helped that there wasn't a lot and it would be back by the time my family got home). Started with the underwear. My mom was very busty so I i found a nice black bra tied with sisters black lace thong.

Then decided to dust off an old favorite, my sisters old school uniform (think navy blue skirt with white top). Popped on some black heels i got from a goodwill, stuffed my shirt and put on a little red wig i found at the same ABS.

I gotta say, I looked good.

I lay down some towels on my moms big bed (chose that cause of the big vanity mirror right across) and started playing with myself. After getting nice and lose I started going to town on my friend and eventually got horny enough to go to grindr.

I posted pictures of myself and said something like “scared girl home alone” and messages came flooding in.After 20 min of looking through messages, I found someone that looked great. He was in his early 30s, Hispanic, HUGE cock and about 4 miles away.

We got to chatting and I sent him some nice pics and he wanted to meet. He said he can host and I agreed with some ground rules.

No real names, last thing I need is this guy hearing my name and recognizing me or my family.

We do what we need and I leave. I'm not looking to cuddle, just get railed.

For the night I will go by the name “Jessie” (though he ended up calling me a bunch of other things

He agreed and sent me his address. I texted my one friend from school, told him the address and if he doesn't hear from me by 12am, call me to make sure im ok.

I decide to stay how i am and put on baggy short and a pull over hoodie, get in my car and pull out of the garage. Within 5 min I was outside the address and the porchlight was on.

I was scared as hell but decided to go for it and step out. As I exited the car I put back on my heels and wig and knocked 4 times as requested. He opened the door shirtless in his shorts. He had a good build: Roughly 5’11, Decent muscles but built wide and kinda overtook my stature.

I smiled and said Hi and he invited me in. He commented on how cute I looked and I said “Thank you mister”. (He liked that)

He asked me to play up the innocence and I didn't object.

We sat on the couch and i did my best proper girl sit (legs bent and together) and acted just as cute as I could be. He said he loved my outfit and decided to lean in for a kiss. I took the moment and before I knew it we were tongue fucking.

Eventually he moves my hands down his body and I feel his massive member starting to get harder. I feel his hand gently push me down on the ground. I smile, giggle and fish out his cock.

“You know what to do,” he says. I just say “Okey Dokey” and swallow it in one gulp.

The next 10 min I am just going to town on him, smiling as I look at him, pawing at his chest and he grabs my head. I pop off and say “Its soo yummy, but I wanted something else”

I get up and slide off my soaked panties and bend over the chair across from him. I wiggle my hips and say “please daddy”.

He sprain up and got some lube on his fresh cock. He standing byhimnd me and I am in agony witing. Then suddenly, I feel cold lube on my ass and moan and lean into it.

30 seconds later he stops and I feel him behind me. Finally, without warning, I feel a hand grab the elastic of my skirt and i feel him slide in. I moan in extasy as I feel it.

After about 20 seconds of adjustment he starts going at me. He keeps saying things like “U like that baby?” “ Are you a good girl? “Your daddy’s little bitch” and the weirdest but hottest one “Dont tell mommy you bitch!”

Naturally, im loving it and im talking right back “ Yes daddy, I wont tell big mean mommy that ur fucking her little sissy boy!” THAT SENT HIM OVER THE EDGE and he went hard as fuck.

As I feel my brain melt im onl driven back yo sanity by the occasional slap on the ass. Suddenly I feel empty, he pulls out and orders me on my knees (I know what about tio happen)

I get on my knees, stick my tongue out and beg for his seed “Please daddy, good sissies get cum!” “Cum on me or ill tell mommy what uve been doing to her sissy boy” “I dont wanna be a boy, i wanna be daddys bitch and bitches get cummy!!!”

Hot, white, thick cream coated my face and ruined my blouse lol. He sits down in exhaustion and I crawl over and continue cleaning his cock for a good 10 minutes. Eventually I tap out and start kissing his cock. He called me a good slut and asked ifI was free another day. I said I was free later this week and he asked for my number. I said fuck it and gave him but kept it under the “Jessie” Name.

I met up with him 2 more times that week (one with a friend of his) and it was a great week.

Went right home, showered, fucked myself till I came all over the bed and passed out wearing my moms babydoll I found in her closet.

Ok so this story was about 14 years ago so bare with me on the details (im going based on my best memory).

Year was 2012 and I just turned 19 earlier that year. I was still in college but was home during the summer. It was just my mom, my 2 sisters (1 older in college) and me. Now I knew I was bi for a long time. I dated girls in HS but only started experimenting with men after I went away to school..

Ive explored a bit, everything from making out at a party to having a guy rail me in his dorm room./I found out I LOVE CROSSDRESSING, but its not needed for me to have fun. I even got daring and bought a “big black friend” from a local adult store.

During this time i discovered 3 things about me: I like men, but PREFER women for more serious stuff, I am a bottom…and I am a slut when I am.

Now the story:

My mom was planning a few days down at the shore with my sisters a few hours away. I HATE the beach and get bored easily so I made a deal with her. I stay, house sit, feed the cats AND in turn I can stay. I was excited for some alone time.

I waited a few hours till they were long gone and thought about how I was gonna spend my week. Was I going to go to a gay club nearby? The ABS? Tease some old men online? NAH.

My first move was to raid my mom and older sister outfits for some fun solo time. I get in the shower and shave my body smooth (helped that there wasn't a lot and it would be back by the time my family got home). Started with the underwear. My mom was very busty so I i found a nice black bra tied with sisters black lace thong.

Then decided to dust off an old favorite, my sisters old school uniform (think navy blue skirt with white top). Popped on some black heels i got from a goodwill, stuffed my shirt and put on a little red wig i found at the same ABS.

I gotta say, I looked good.

I lay down some towels on my moms big bed (chose that cause of the big vanity mirror right across) and started playing with myself. After getting nice and lose I started going to town on my friend and eventually got horny enough to go to grindr.

I posted pictures of myself and said something like “scared girl home alone” and messages came flooding in.After 20 min of looking through messages, I found someone that looked great. He was in his early 30s, Hispanic, HUGE cock and about 4 miles away.

We got to chatting and I sent him some nice pics and he wanted to meet. He said he can host and I agreed with some ground rules.

No real names, last thing I need is this guy hearing my name and recognizing me or my family.

We do what we need and I leave. I'm not looking to cuddle, just get railed.

For the night I will go by the name “Jessie” (though he ended up calling me a bunch of other things

He agreed and sent me his address. I texted my one friend from school, told him the address and if he doesn't hear from me by 12am, call me to make sure im ok.

I decide to stay how i am and put on baggy short and a pull over hoodie, get in my car and pull out of the garage. Within 5 min I was outside the address and the porchlight was on.

I was scared as hell but decided to go for it and step out. As I exited the car I put back on my heels and wig and knocked 4 times as requested. He opened the door shirtless in his shorts. He had a good build: Roughly 5’11, Decent muscles but built wide and kinda overtook my stature.

I smiled and said Hi and he invited me in. He commented on how cute I looked and I said “Thank you mister”. (He liked that)

He asked me to play up the innocence and I didn't object.

We sat on the couch and i did my best proper girl sit (legs bent and together) and acted just as cute as I could be. He said he loved my outfit and decided to lean in for a kiss. I took the moment and before I knew it we were tongue fucking.

Eventually he moves my hands down his body and I feel his massive member starting to get harder. I feel his hand gently push me down on the ground. I smile, giggle and fish out his cock.

“You know what to do,” he says. I just say “Okey Dokey” and swallow it in one gulp.

The next 10 min I am just going to town on him, smiling as I look at him, pawing at his chest and he grabs my head. I pop off and say “Its soo yummy, but I wanted something else”

I get up and slide off my soaked panties and bend over the chair across from him. I wiggle my hips and say “please daddy”.

He sprain up and got some lube on his fresh cock. He standing byhimnd me and I am in agony witing. Then suddenly, I feel cold lube on my ass and moan and lean into it.

30 seconds later he stops and I feel him behind me. Finally, without warning, I feel a hand grab the elastic of my skirt and i feel him slide in. I moan in extasy as I feel it.

After about 20 seconds of adjustment he starts going at me. He keeps saying things like “U like that baby?” “ Are you a good girl? “Your daddy’s little bitch” and the weirdest but hottest one “Dont tell mommy you bitch!”

Naturally, im loving it and im talking right back “ Yes daddy, I wont tell big mean mommy that ur fucking her little sissy boy!” THAT SENT HIM OVER THE EDGE and he went hard as fuck.

As I feel my brain melt im onl driven back yo sanity by the occasional slap on the ass. Suddenly I feel empty, he pulls out and orders me on my knees (I know what about tio happen)

I get on my knees, stick my tongue out and beg for his seed “Please daddy, good sissies get cum!” “Cum on me or ill tell mommy what uve been doing to her sissy boy” “I dont wanna be a boy, i wanna be daddys bitch and bitches get cummy!!!”

Hot, white, thick cream coated my face and ruined my blouse lol. He sits down in exhaustion and I crawl over and continue cleaning his cock for a good 10 minutes. Eventually I tap out and start kissing his cock. He called me a good slut and asked ifI was free another day. I said I was free later this week and he asked for my number. I said fuck it and gave him but kept it under the “Jessie” Name.

I met up with him 2 more times that week (one with a friend of his) and it was a great week.

Went right home, showered, fucked myself till I came all over the bed and passed out wearing my moms babydoll I found in her closet.