My name is Paul, I’m rapidly approaching retirement age, I have a happy life with my wife, Alice who is 5 years younger than me (though she actually looks about 10 years younger than that)
We have two children, Ian who is still single (living in Scotland) and Charlotte who is married and expecting twins in a couple of months. Charlotte is married to a lovely chap, Richard. We all get on so well, often holidaying together, life is good.
Despite all this apparent bliss I do have a dark secret lurking beneath the surface, I am a secret crossdresser (Alice knows nothing of this and it would spell instant divorce if she ever found out) I’ve tried stopping several times but always seem to return to my naughty ways.
I figure that as long as nobody knows, and I’m not harming anyone I can keep my little secret.
I do like to go on cam and be humiliated for being a small cocked sissy but that’s as far as my perverse secret goes.
I love reading sissy stories and although I’m envious of the crossdressers in these stories who take things further or who are made to go beyond their boundaries, there is no chance I would ever be so brave (or so stupid?) I’m more than happy to simply stay within my comfort zone.
Recently Son in law Richard has been working abroad and we’ve not seen so much of him so we were delighted to get an invite from him and Charlotte for when he returned to the UK, we were really looking forward to visiting them for what would be a long weekend. They live about 60 miles from us.
When we arrived on the Friday we quickly unloaded our cases from the car , we began relaxing immediately. Soon the vino emerged and we all enjoyed the first of what promised to be a wine filled weekend.
After a short while we walked to their local for an evening meal. What a pleasant evening we had, wonderful food, some nice wine (quite a lot of red consumed by each of us)
Richard introduced us to the landlord and landlady who they’d seemingly become friendly with, Alex and Rita, a lovely couple from Jamaica.
Alex looked quite intimidating at first glance, being 6’2” with muscles to match. but was the nicest chap you could wish to meet, his wife was the life and soul of the evening and we didn’t stop laughing (or drinking)
Eventually we staggered back to Charlotte and Richard’s house at the end of the evening and discussed what we all might do for the rest of the weekend. Charlotte and Alice decided to go shopping at the local mall the following day (Saturday)…saying they’d likely be out for the whole day.
Richard said he had some paperwork to do in the morning but we could go back to the pub to catch the lunchtime game on the large screen tv
After Richard and myself consumed even more alcohol we all eventually went to bed.
It seemed very early when I heard Alice get up, get dressed and say goodbye for her shopping trip (no sign of being hungover…bitch)
I drifted back off to sleep still feeling the effects of the previous nights drinking. When I eventually got up (10:30 ish) I showered and dressed. Headed downstairs and found the place to be empty I recalled that Richard said that he would be doing some paperwork so headed to his home office in the garden to see if he’d like a tea or coffee.
Imagine my shock and total surprise when I opened the door to his shed to the look of shock and total surprise on Richard’s face. He was wearing a red babydoll with matching panties and black fishnet hold up stockings.
For a long while neither of us said a thing… he was like a rabbit caught in the headlights
“Shit shit shit!” He exclaimed, slamming his laptop shut “I totally forgot you were here, I thought I had the house to myself, I am so sorry you’ve seen me like this”
“Calm down” I said “you’re not harming anyone are you”?
“Does Charlotte know” was my next question
He dipped his head and said “No! She’d kill me if she saw me like this”
“Then you’re secret is safe with me” I reassured him
“Seriously? …seriously? I thought you’d freak out”
I swallowed my better instincts and said “ I could hardly freak out when I'm also guilty of the same secret”
His face was a picture of disbelief you could see his mind trying to process this new fact
“Seriously????? No!!! You’re joking!!!! Seriously????? I am so fucking stunned, I never thought for one moment I’d ever meet another crossdresser, and never in a million years would I have dreamt that it would be you”
He had so many questions, how long I had been dressing? did anyone know? Favourite underwear etc
“I really like your babydoll” I said,” very envious, always loved babydolls, can I safely assume you’ve were watching porn before I rudely interrupted you , what sort do you like?
Richard smiled, looked a little distracted and let out a slight laugh “ I was going to say “just the usual stuff”, but it’d be pretty obviously that dressed like this My choice of porn wouldn’t be “usual stuff”….I like sub/Dom, sissy Hypnos, Sph Joi a bit of interracial stuff as well. What about you”?
“Pretty much the same plus stories of being caught wearing , oh and I quite like humiliation videos and stories That sort of stuff”
Through all this talking it was strange but there was no hint of attraction or a desire on either of our part to do anything with or to each other, I think we were both too submissive. Also the “in law” relationship was awkward to say the least, we probably both still a little bit in shock
Eventually Richard said he ought to be getting changed so that we could head to the pub to watch the football
20 minutes later we were wandering to the same local that we went to the previous night. As we entered the bar Alex the Landlord beckoned Richard over for a private word meanwhile I found us a table in a prime position to watch the game. Richard was gone about 20 minutes and even missed the start of the game. He looked a bit flustered and apologised for keeping me waiting. He couldn’t stop saying sorry. It was like he was apologising for something more than just keeping me waiting. I told him to forget about it and enjoy the game.
At halftime Richards phone pinged with a text message, he again apologised but this time said something about having no options. I was totally confused, then he said that Alex the landlord had mentioned that he would like a word with me upstairs.
Having only just met the guy I couldn’t begin to imagine why this nice chap would want a word.
I climbed the stairs to the pub’s private rooms. I knocked on the door to Alex’ office.
“Come in”
I opened the door.
“Come on in Paul. Was lovely meeting you and your gorgeous wife last night can’t believe how awesome she looks for her age. She’s still very sexy”
“I’m very lucky to have her” I replied “she is amazing, I’d be lost without her“
“That’s so lovely that you’re both still devoted to each other after being together for so long. I’m sure you’d be devastated if anything came between you….
I asked you to pop up for a chat because I’ve got an offer that I’m sure you won’t want to say no to“
“OK” I said without a clue what he was talking about. I’d barely met the guy so couldn’t imagine what he could possibly be talking about
“I made a similar offer to your son in law Richard last year… unless you do exactly as I say I will be telling your gorgeous wife that you secretly dress up in sissy clothes whenever she’s out of the house. So, from now on you are going to join Richard as my bitch, I take it that’s ok with you? “
I felt all colour drain from my face, indeed from the whole of my body. I couldn’t believe Richard had betrayed me. I said to him that his secret was safe with me I didn’t think for one moment that my secret wouldn’t be safe with him
“You’re obviously wondering why Sissy Richie revealed that you’re also a fucking sissy …you see, I was on a video call with him this morning and he suddenly closed his laptop and cut the feed… apparently you had just entered his office. When you both arrived here earlier I demanded to know what pathetic excuse he had for spoiling my enjoyment of seeing him humiliate himself on camera. He explained that he had been caught, so I pressed him to tell me by who and what the reaction was. If he hadn’t told me, I was going to expose his sissy secrets to your daughter and all of their friends, so you can imagine his dilemma between landing you in it and allowing his secret life to continue as normal”
I was speechless my heart racing and my mind cursing Richard but more so Myself for stupidly revealing my secret.
Alex continued,
“Seeing as you are the one who ruined my morning amusement you really need to make it up to me, don’t you think?. “
Alex pointed to a pile of assorted lingerie behind me.
“If you want to watch any of the rest of that football match you’d better put those on at double speed. Come on Sissy. Move it”
Oh My God was all I could think. My worst fears and favourite fantasies were merging into real life. I didn’t see I had any choices. I picked up a pink suspender belt.
“Good choice. Pink will suit you sissy!”
I found matching bra panties and a pair of black fishnet stockings. Hesitantly started to remove my shirt then jeans and then socks and underwear.
Alex began laughing “your cock is even smaller than Sissy Richies, Alice will be blown away when she compares the size of my cock against the pathetic excuse you’ve been giving her all these years. Just wait til Alice becomes addicted to it. She will be begging me to fuck her.
I was by now wearing the chosen lingerie
“Don’t you look the pretty one Sissy Pauletta!” Don’t you think you should thank me for allowing you to look so feminine “?
Quietly I replied “thank you”
“ Now then that’s not very convincing is it. Say it louder like you mean it because I’m sure you do mean it, don’t you sissy?”
“Yes Sir , sorry sir thank you so much for allowing me to feel so pretty “ in reality despite this enforced humiliating situation I found myself in I was actually feeling quite turned on, my 4” cock was beginning to grow with a very noticeable quantity of pre cum leaking into the front of my pink panties, a fact that I’m sure Alex noticed.
“Ha ha! You pathetic fucking sissy You’re actually enjoying this aren’t you? You’ve been craving this sort of humiliation haven’t you?
I dipped my head but almost imperceptibly nodded
“don’t you think you should be kneeling at my feet and unzipping my trousers for your reward as thanks?”
I felt I had no choice but to comply, I was on my knees and unbuttoning Alex’ trousers and unzipping his fly. There was a huge inviting bulge in his boxers, I couldn’t control my gasp
“You’re practically salivating Sissy. You just can’t wait to get your lips around it can you”? Alex gloated
“Please Sir would it be alright to see it” I said timidly
“Look, lick and then you can suck it, you stupid fucking sissy “
Omg! This was really happening I was going see feel and suck a cock (only in my wildest dreams did I ever think this might happen for real. )
I released Alex’s 8” from his boxers, it was as impressive as I’d ever seen, fatter than I’d imagined. I felt Alex’s hand on the back my head slowly moving it closer to his throbbing erection. Millimetres from it I opened my mouth and allowed it to enter, the sensation of having my mouth totally filled, invaded was so intense. The musky smell was overwhelming and addictive. Once it was in my mouth I began to devour the salty taste. It was an instant sensation of wanting to pleasure Alex as much as possible.
I have no idea how long I was sucking but suddenly Alex pushed me off him in that instant he came on my face.
“Don’t wipe it off slut” he said, straight away he did something with his phone (I guess he’d been taking pictures of me, not that I’d noticed before. )
I was recovering when there was a knock at the door. I turned my back to it. Not wanting anyone to see me like this.
“Come in sissy Richie”
I looked to see. Richard on all fours enter the room, immediately strip down to his panties and crawl over to Alex.
“Sissy Richie you need to help your sissy father in law to clean up a little. Lick that lovely cum from his face you pathetic slut. “
Richard could barely look me in the face.
He whispered almost inaudibly. “I am so sorry I got you into this”
He proceeded to eat Alex’s jizz from my face.
After I was clean tho still wet from his tongue.
“I think a way of thanking each other for a pleasant interlude a 69 would be appropriate don’t you think sissies?”
We looked at each other. Realising we had no choice in this. I sucked my second ever cock and had the admittedly stunning sensation of having my own simultaneous blowjob
“Both of you look at me and smile” we both complied
“ This video will make such a wonderful gift for Alice and Charlotte if you don’t do exactly what I want, when I want it. “
As he said these words I felt Richard cum in my mouth which had the knock on effect of tipping me over the point of no return. It felt wonderful cumming so hard.
“Ok! I’m bored with you both now, get changed and go back to whatever is left of your football match” Alex said dismissively “oh and keep your new underwear on Sissy Pauletta”
After dressing we headed back to the bar, although I did say we should head straight back to the house
“Alex will take it very badly if we don’t stay at least til the end of the game” warned Richard
There was only 10 minutes to go so not a huge nightmare. Rita was serving behind the bar, it seemed strange after what we’d both just done to try to behave normally in front of Alex’s wife.
Bloody 10 minutes of extra time prolonged the agony of having to stay in the pub.
Final whistle blew and I left my seat before Richard realised we were leaving.
Alex had emerged at this time and waved us off.
“Enjoy the game boys?” He said smiling “see you again soon”
As soon as we were back in the open air again Richard couldn’t stop apologising for getting me into this situation.
I was virtually silent as we walked back to the house.
I removed the lingerie as soon as we got back though kept it and hid it in a pocket of my case.
When I headed back down stairs I just said to Richard “can we not discuss any of today, it’s probably best forgotten”
Richards phone pinged at this time a message from Charlotte
“Hiya hope you both enjoyed the game. We’re heading back now. Had a text from Rita 10 minutes ago asking if we wanted to book a table for Sunday lunch. I’ve already said we’d definitely go along. Hope that’s ok! See you soon”
Richard read it to me. My head in my hands. We have to go through hell being in same room as Alex, with Alice and Charlotte there making it impossibly awkward.
Having drunk far too much on Friday we all decided on a quiet night in with a takeaway for Saturday night.
Sunday morning was quite subdued then about 12:30 we headed to the pub for Sunday lunch.
Alex greeted us all like we were long lost family. His behaviour didn’t reflect at all what he held over myself and Richard. He briefly hugged us both then gave Charlotte a huge lingering hug ending with a delicate kiss on the lips. Then he looked at Alice
“Come here sexy” and gave an even longer hug to Alice. Ending with a squeeze of her bum cheek and a kiss on the lips. I wondered for a brief moment if Alice could feel his 8” cock as he was pressed that tight to her.
Alice seemed to take it all in good humour and laughed off his affections
“Leave the poor woman alone” shouted Rita.
“can’t you see she’s happily married “
Alice didn’t know where to look. She was bright red and visibly flustered.
We were led to our table by Rita. As we were all having the roast she immediately took our order then whispered to Alice (though in my earshot)
“I am so sorry for his behaviour, he seems to think just because he’s got a huge cock, every woman will be all over him”.
It was as if Rita was planting a seed of interest in Alice’s mind for it to grow.
Alice has only ever been with me and was only accustomed and presumably satisfied with my 4” so I assume the idea of a cock twice the size of mine was not something she’d really thought much about before.
The meal was uneventful after that, as we got up to leave both Rita and Alex came to our table to say goodbye. Thankfully this could well be the last time I had to see this imposing man at least for a very long while. Richard and myself had normal hugs from both Rita and Alex. Charlotte and Alice had sweet kisses on the cheek from Rita then Charlotte had a more affectionate hug and Kiss from Alex. When it came to Alice Alex lingered just a little longer than was comfortable but I swear I saw Alice thrust her body tightly against Alex’ crotch area. Omg she was trying to feel the size of his monster cock. The look on her face when they parted from their hug told me she was impressed.
We left to go back to the house before packing our bags and leaving about 4:30pm on the Sunday. Alice had to work on the Monday so we darent leave it any later.
I was so relieved to get home and escape the clutches of Alex. Poor Richard. He had no such luck
After a quiet evening and night in our own bed we woke early on Monday morning. I had a couple more days off until my return to work so had a bit of a lie in. I said goodbye to Alice as her shift began at 8:30 and I drifted back to sleep.
When I eventually woke I had a glorious stiffness which demanded my attention. It felt wonderful stroking my erection but I was quickly reminded of the underwear that that bastard Alex had made me wear. Bizarrely I missed that set of lingerie, I found my bag and was soon wearing the same underwear I had been so humiliated in. The memory of that humiliation was somehow intensely inspiring. I was loving reliving that experience (ok only in my head I really didn’t want a repeat experience, although I think in that moment I’d have begged to be sucking Alex’ throbbing erection in a heartbeat, but definitely no, not in real life).
Easy to think that way knowing there was no chance of it happening. I went to the study where the PC was set up, I needed some sissy porn to edge to. Maybe featuring some big black cock.
As soon as the PC fully logged on I received a notification of awaiting emails. I did not want to be distracted at this time by what was probably spam. So ignored it and opened the browser (in safe mode) and found some crossdresser humiliation videos.
Another ping indicating another email
Reluctantly I opened the email program. There were several from Richard. Three from Alex and a couple of work related messages
The first, from Richard, had been sent almost immediately after we’d left and was yet another apology, the second which was sent early this morning was also an apology, this time for sharing my email address (and also Alice’s) with Alex, again he said he was given no options but to do what Alex told him.
Shit! Shit!Shit!
I hesitantly opened the first from Alex. It contained a series of pictures , very clearly showing my face, showing the lingerie I’d been wearing, showing my lips sucking eagerly on a huge black cock. Also a video showing Richard and myself sucking each other complete with us both looking at the camera…no mistaking who it was.
The second email contained a link to a swinging site telling me to log in to a room (password was included)
The third email said
You have until 11am to login to the “Sissy in law” room and turn on your camera or the contents in the first email will be sent directly to Alice. Shit! Shit! shit it was 10:57. Only 3 minutes no time to think just time to comply.
I clicked the link found the room
Entered the password
Entered the room , it was 10:59
Clicked on the button to open my camera… sodding PC taking forever to load. Camera was on with just 2 seconds before the clock switched to 11am.
I noticed there were two other cameras active.
I opened them both. The first one was just a blank screen, the second was Richard wearing black bra panties suspender and black silky stockings sucking on a huge black dildo.
As soon as I opened camera #1 I heard the familiar sound of Alex laughing.
“Oh my god!!!! You couldn’t even wait to dress up again in the pretty panties you wore for me. You are even more pathetic than I would have ever guessed. I bet you were craving my big black cock. I bet you were reminiscing sucking it.“
The combination of my bowed head and my full (though inadequate) erection tenting my pink panties betrayed my thoughts. Alex was more accurate than I’d ever want to admit.
“I’ve got a surprise for you cocksucker Pauletta “ said Alex
At that moment the front door bell rang, it didn’t matter who it was I darent answer the door.
“Aren’t you going to answer that Sissy?”
I mumbled “I can’t go dressed like this”
“ Go and answer the door Pauletta, do as you’re told fucking little sissy!”
Against my better judgment I made my way to the front door, nervously I looked through the spy hole
A delivery driver or at least someone who looked like a delivery driver was standing with a parcel. He rang the bell again and knocked loudly.
I opened it slightly and asked politely if he could leave the parcel on the doorstep and I’d take it in later.
“Sorry Pauletta. I’m under very strict instructions to deliver this right to your computer room” He barged past me.
I closed the door and followed the delivery driver through to my awaiting camera.
Richard was busy on camera still sucking hard. Alex’ voice boomed as he laughed at my predicament
The stranger delivering the parcel threw it at me I caught it and Alex said
“I thought you might enjoy a reminder of our previous chat, open up your gift it’s exactly the same as Sissy Richie’s”
I opened to reveal a “mould your own cock” dildo, black and exactly the same as Alex’s
Once I’d opened the “gift” the delivery driver began to unbuckle his belt and unzipped his jeans
“I think it would be a nice way for you to thank Leroy for delivering your gift”he paused,”on your knees Pauletta!!”
My fate was sealed. I wrapped my lips around Leroy’s 6” and began pleasuring him
All of this on cam for Alex’s amusement.
I knew at this point my nightmare would never end.
Sent from my iPhone
