We were visiting J*ck & Johan, my parents-in-law, for the day. My wife and J*ck had gone out on an errand, leaving me alone with Johan. As we were setting the table for lunch, Johan suddenly blurted out to me: ”I know what you do”
{Oh-oh where is this going?}
Not sure what you mean by that, Johan {drinking in the sight of her lovely huge tits encased in an exquisite white lacy M&S bra, the cups and straps of which her slightly see-through blouse was failing to hide}
You wear my panties.
{Took her long enough.}
I’m sorry? {pretending to be shocked} what did you say?
I know you wear my panties. It’s a disgusting habit. You should be ashamed of yourself.
How did you come to that conclusion?
{Oh-oh, I fucked up somewhere…}
I noticed stains on the front of a pair of panties when I was dressing this morning.
{Quite high-up stains because I always get a raging hard-on when I wear your panties, I wanted to say}
Are you sure?
Of course I’m sure. I had the same issue with my own pathetic husband years ago.
Maybe the stains were his? {poor attempt but you gotta try, right?}
Oh no, nowadays he rarely cums and when he does, only one or two drops. This stain was a big one.
{I blushed. And I know why he rarely cums near Johan because he saves it all for me. Every drop. I am J*ck’s sissy. Oh he can satisfy ME.}
I am very sorry that I put you through that, Johan. How will we sort this out?
{I wanted to sort it out by ripping off her blouse to expose her glorious bra-clad tits, throwing her onto the bed on her front, raising her skirt, pulling down her panties and giving her the first arse-fucking off her life.}
Well, I thought in the first place I would tell our daughter your wife what a hopeless man she has.
{Oh she knows that}
Oh please don’t do that!
And of course I’d have to tell J*ck my husband.
{Waste of time, that. He is well aware that I wear his wife’s underwear. He usually supplies it}
Oh no, please don’t!!
But in the end I decided to keep it to myself. But you have to promise to do me a favour.
Oh of course I’d be happy to. What do you want me to do?
Well for years now J*ck and I have not been having sex.
{Yep, cos he’s fucking me regularly. Sissies 1 big-titted sluts 0}
Oh really? I didn’t know that, I mean how would I, nothing to do with me.
But now that I’ve seen some photos of you dressed as a sissy - is that the right term? - I think there is something you and I can offer J*ck.
{Oh-oh, I wonder what photos she’s seen, and how she got hold of them?}
Ah, yes, that is the correct term. What photos could you possibly have seen of me, Johan?
A friend of mine found out from her son about a website where men dress up in women’s clothes and let other men make love to them.
{Shit. newtransnudes. I’m in big trouble}
Ah, yes, I’ve heard about that sort of thing.
Heard about it? My friend’s son showed me many photos of you wearing my bras and panties and blouses and skirts, with other men sticking their willies up your bottom, or putting their willies in your mouth. Sometimes 2 men doing those things to you and even splashing their semen over my underwear!. As I said before, you should be ashamed!
{Luckily no photos of her hubby fucking me exist. Dodged a bullet there}
Well, Johan, you do seem to have caught me. What do you intend doing about it?
{I was in deep trouble now, so didn’t see much point in just giving up}
J*ck has always been trying to persuade me to let him put his willy up my bottom. Frankly the idea sickens me, but he’s very persistent. I think I’ll suggest to him that he can do that horrible thing to you. After all a bottom is a bottom.
{Trust me, Johan, some bottoms are tighter and deeper than others. I can take a 15-inch monster cock. }
Well I suppose if that is the only way of ensuring you keep quiet about it then I will certainly go along with your plan. But I have one small request?
Well what is it?
Can you ask J*ck which of your bra and panties he’d like me to wear? Maybe even a blouse and skirt?
Oh yes that is a good idea. A good sissy always wears sexy underwear - apparently - and I have quite a good selection for Jack to choose from.
{Don’t I know it, there is not one single item of Johan’s underwear that I haven’t worn and cum into or over}.
Just then the front door opened.
Johan hissed at me: We’re not finished with this. I’ll find a time to see you with J*ck and we’ll get things sorted out. You’re such a disappointing son-in-law.
{As she said this I came ferociously. In her panties. How was Johan to know I was wearing her panties? I so hoped she hadn’t seen the smile on my face as I came, or heard the pumping of my erect cock as its glazed the material of her white cotton panties with my sissycum}.

To be continued

My name is Bill, I travel in ladies underwear! No, really; I am the director of a Lingerie company so I travel all over the UK for meetings with suppliers, designers, shops, etc. I am also a crossdresser and have been for years. So I have a legitimate reason for having a stock of lingerie in my car or desk, lucky guy, right?

After a long business trip I was on my way home when the heavens opened and the road become impassable due to the torrential rain. Luckily there was a service area just ahead so I pulled into it. First priority was to relieve myself. I made my way to the main building, I took my briefcase with me into the toilet to find an empty cubicle. Dropping my trousers and easing my black lacy panties down I sat to pee like all females do. I couldn’t resist stroking my suspender straps and stocking tops.
Pulling three sheets of paper I eased my skin back and wiped my mushroom-headed cock dry, can’t have damp panties. I left the cubicle and washed and dried my hands. Leaving the toilets I bought myself a hot drink and snack. I noticed a sign for a Travelodge. I wonder if they had a spare room? I approached the receptionist to enquire. Asking the question, I got a response, ‘Sorry sir the last single room has been taken. We do have a twin available.’
“I’ll take it.” a voice over my shoulder said. The young man behind me forced his way forward thrusting his credit card at the receptionist.
He was dripping with water and visibly shivering. The receptionist told him I was first. Taking pity on him I suggested we share the cost so he could shower and change, get warm and wait out the storm. I only really needed a bed for the night. It was agreed.
For the first time I looked carefully at my “overnight guest” and was surprised to see that I knew him. “Aren’t you Jock & Joan’s son-in-law Paul?”
Indeed I am, and I’ve just recognised you, you’re a neighbour, aren’t you?”
“Yes I’m Bill, I was at your wedding.”
By now we had reached the hotel room.
Entering the room, I offered my new acquaintance first use of the bathroom.
“No you go first, then I can hang my wet clothes up to dry.” Pete replied.
I obviously couldn’t remove my trousers but I did remove my shirt and put it on a door hook. Shoes off next placed by the radiator.
I walked casually into the bathroom aware of my stockings being pulled up by my suspender straps. In the bathroom I quickly divested myself of trousers and lingerie. Soon showered and with a towel wrapped around my waist I returned to the bedroom. With my lingerie carefully hidden in my rolled up trousers.
“Your turn.” I informed Paul, although it was obvious.
He smiled and replied “Thanks pet”.
Pet? Oh well it might be usual from his part of the country.
“I’m exhausted, I’m going to get straight into bed.” I told him.
Paul took some dry clothes in the bathroom with him, wrapped in a towel.
I opened my briefcase and took out a clean pair of white silky nylon panties quickly putting them on. I put my worn stockings, suspender belt and panties inside and closed the lid. I slid my briefcase under my bed. Climbing into bed I switched off my cabinet light. The room was semi dark as Paul had turned off the main light and only his cabinet light remained on, giving a soft glow. In bed in the warm I was getting sleepy. My eyes were slowly closing. I saw Paul exit the bathroom through half closed eyes.
Mmmm it looked like he was wearing an old type night shirt shoulder to mid thigh. As he walked closer my eyes suddenly opened.
“What are you wearing?” I asked noting the lace trim around the neck and hem.
“More to the point what are you wearing?” Paul replied.
“Well not a pretty nightie like you.” I answered.
“You mean you’re naked.” Paul stated.
“Not exactly.” I blushed as I spoke.
“Mmmm sounds interesting.” Paul spoke as he turned down his bed. Bending at the waist he displayed his lacy backed panties in a delicate shade of pink.
“Cheeky.” I whispered.
“Ooh sorry.” Paul answered giving a little wiggle.
He sat on his bed about to get in.
“Now I’m disappointed.” I told him.
“Oh why?” He responded.
“Because you’re over there, and I’m over here.” I told him.
“And how would you like it then?” Paul responded
Throwing the duvet back exposing my white panties that had started to bulge at the sight of his nightie and his cheeky wiggle.
“That bulge looks tempting and I think it needs investigating.” Paul exclaimed.
“Come and get into my bed Columbo.” I instructed.
Paul slid in next to me, his soft nightie caressed my body, my nipples erected as it touched them. Soon our lips were pressed together our tongues were searching for a way into each other’s mouths. As we kissed passionately I could feel his hardness pressing against mine. I reached down and encompassed it stroking it through his nightie.
“Oh that’s wonderful, but steady or I’m going to cum too quick, I want it to last.” Paul gasped, as we broke from kissing.
“When you do, I want it inside me. I don’t care where.” I was so turned on.
“Shall we remove our panties?” Paul asked.
“Oh yes, please can I remove yours first?” I answered.
“Be my guest.” Paul responded.
I swivelled in the bed, nearly falling out. Soon we were top to toe and my fingers were slipping into Paul’s waistband easing them off. My own panties were being pushed down my legs. With both our panties removed I turned my attention to the beautiful hard cock presented before me. Taking gentle hold and stroking it I exposed the mushroom head that had already started leaking pre-cum. My tongue flicked out to taste it.
“Ooh, Mmmm. That’s nice, but be careful I might cum.” Paul gasped.
“I want your cum now, and we have got all night.” I uttered before sinking my lips over the head of his engorged cock, licking all over it including his most sensitive frenulum.
“Oh, ah, mmmm, yes, oh no.” He was now thrusting into my mouth as his passion and orgasm rose.
I couldn’t say much with my mouth full of his hard flesh, soon not only his cock in my mouth but his delicious sissyseed was pumping in as well. I quickly gulped and swallowed, ready for the next spurt. I wasn’t disappointed, in fact there were at least 5 spurts before it reduced to a dribble. What was amazing for me was he stayed hard. I normally deflate soon after I have cum. So I carried on bobbing up and down.
“Wow, I’m still hard, but now it’s your turn.” Paul told me before his mouth engulfed my cock.
Paul was good, very good. He kept me on the edge of blowing my load for at least 10-15 minutes until he decided he was ready for me.
Oh my goodness, I don’t think I have ever cum so much, to me it felt like 5 orgasms in one load. Paul was sucking and swallowing until there was none left and I was exhausted. He got out of bed saying.
“That was the best and tastiest tummy full of cum I’ve ever had, thank you sweetheart.”
“Paul.” I started.
“Joan, please. I prefer Joan when I’m in my femme mode.”
“Joan darling, you are still sporting something of a very non femme bulge under your nightie. Please can I help, oh and I’m Bea when dressed.”
“That would be fantastic, it’s never happened before. Oh and you aren’t exactly dressed.” Joan replied.
“Easily rectified.” I told her reaching for my briefcase. Opening it I took out my suspender belt and stockings also the bra that I hadn’t been wearing earlier. The sexy white lacy bra supported my little puffy tits and I noticed with satisfaction that my erect nipples could be seen protruding through the gossamer lace of the bra cups.
Quickly putting the lingerie on I turned to Johan.
“Ta dah.” I exclaimed.
“You forgot your panties Bea.” She uttered.
“For what I have in mind, I won’t need them.” I told her.
“Oh wow oh yes.” She said as she returned to my bed.
“Let’s see if we can push the beds together.” I suggested.
“Good idea.” She replied.
We soon had them side by side. I knelt on one bed with my arms folded on the other. My anal pussy presented to my new young lover.
“Please be gentle sweetheart, it’s virgin territory.” I pleaded, smiling ironically.
“Me too, I’ve often thought about it but have never given or received it.” Joan whispered huskily.
“Perhaps we can rectify that before the night is through.” I saucily replied.
“Oh what a wonderful idea.” Joan gushed.
Climbing behind me I lowered my head onto my forearms, presenting myself to her. I felt her nudging my rosebud entrance. Exerting pressure to attempt entry.
“Wait, don’t go anywhere, I have some hand cream to lubricate you my darling.” Joan uttered as she crossed the room to her case.
Returning I felt the coldness, which made me gasp as she applied it pushing her finger in past my sphincter. She then withdrew her finger and once again offered her hardness, now lubricated.
Joan pushed and slowly slipped past my outer muscles. I thrust my hand into my mouth to stifle any noise I could have made. We were in a motel and the walls were quite thin, I suspected.
Joan stopped pushing, discerning my discomfort. As the pain subsided I pushed back onto Joan taking her into me until her tummy was touching my bum cheeks. We stayed fully joined for a few minutes until I was comfortable. I started to move forward then swiftly back until my lover took over. She held my hips caressing my suspender straps as she took over our love making.
I could feel her silky nightie tickling my lower back as she moved in and out.
Our combined efforts gave me a truly wonderful feeling. While Joan was moving in and out, with muscles trying hard not to let her pull right out, I moved one hand down to my cock to find it semi-hard and leaking precum.
“I’m very close to cumming darling.” Joan gasped.
“Fill me with your cum, I want it all deep inside me.” I gasped trying to catch as much cum I was leaking.
She did, giving a final thrust. She emptied more of her creamy baby juice as far inside me as could. Withdrawing from me her limp cock glistening with our combined juices she collapsed face down on the bed. Almost perfect.
“Right sweetheart lift your gorgeous derrière off the bed, it’s your turn.” I almost commanded.
Joan complied and using my own natural juices I held in my hand I lubricated us both. I pressed on her rose bud, with the addition of my juices I managed to invade her anal pussy.
“Ooh steady darling. Mmmm a bit more, steady, mmmm more please.” Joan gasped back at me. It took a while but eventually I was fully home. My hands resting on his hips covered by his nightie.
“Tell me when you are ready sweetheart.” I spoke softly in her ear.
“Gently to start please.” She answered.
“Of course.” I breathed heavily.
I started slowly and of course gently, I didn’t want to ruin a beautiful moment.
“Oh darling, if I’d known it was this good, I would have done it sooner or at least bought a toy.” Joan gasped.
“Almost what I was thinking.” I replied trying desperately not to orgasm too soon.
“Faster darling, I need you to fill me, make me pregnant even.” Joan was gasping for air.
Like I could make her pregnant, but I wasn’t going to spoil a minute of our love making.
“Oh goodness, I can’t hold on much longer.” I spoke as I increased my speed and our love eggs were touching as I was fully inside her.
“Yes, yes, yes. Fill me now.” She was obviously in the throes of an orgasm herself.
I just relaxed my control and my cum pumped into her. Spurt after spurt.
I fell forward onto her back and she collapsed on the bed. I was still inside her and could feel her muscles squeezing the new life seed from me.
We both lay still for a while to get our breathing to normal. Then I moved off as I had slipped out of Joan’s love tube.
“Stay where you are, and don’t move.” She ordered. Moving swiftly to the bathroom she returned with a large bath towel.
“Raise your gorgeous sissyass into the air darling.” She told me.
I did and she slid the towel underneath me.
“Stay like that.” She continued.
“Are you ready to go again?” I asked looking at her deflated cock, it still looked very suckable.
“Not yet, but we don’t want to leak out baby juice.” she told me as I heard paper being torn. She moved behind me and I could feel something being eased into my love tube.
“There now here’s another, please insert it into me then we can sleep for a while safe knowing we won’t leak.”
Johan passed me a tampon. I unwrapped it and inserted it into her. She sighed as it settled into place. Then she put on her discarded panties. I also replaced mine.
We lay on the bed as Joan spooned behind me, her hand around me teasing my nipples through my bra.
“Good night darling, and thank you for taking my virginity tonight it was wonderful.” Joan whispered in my ear.
“ I hope we can do it again.” I whispered back.
“Not for a while, I need to refill my love eggs for you.” Joan replied sleepily.
“Mmmm me too.” I answered.
Soon we were asleep.

Something woke me in the night. Not Joan’s cock nudging against my panties.
Through the wall I could hear raised voices, not in anger, but in passion.
‘Fuck me big boy, fill my arse with your cum. Then I’ll suck you clean’. The voice almost shouted.
I nudged Joan awake, holding a finger to her lips.
“Listen, someone in the next room is having sex, anal sex.” I whispered.
“Someone in this room wants anal sex, but I need to remove the tampon.” She whispered back.
“Are there anymore?” I enquired.
“No but there are panty-liners.” She replied.
Before long two moist tampons were nestling in a sanitary bag in the bin.
Joan was lying on her back, her legs on my shoulders as we made love again, this time in the missionary position. I could look at her pleasured face, her gorgeous hard cock waving and leaking. I once again pumped my seed into her, while listening to the sounds emanating from the next room.
We swapped positions. Joan now entered me, my flaccid cock now resting on my tummy.
Her entry was easier now as mine had been. It wasn’t long before Joan whispered she was about to cum which coincided with the noises next door.
‘Oh fuck yes, I’ll be leaking for a week, you must have put a gallon of spunk in me’. Came from next door.
Joan and I suppressed our giggling. Putting our panties back on, now with panty-liners to catch any leakage, we once again settled to sleep. This time I spooned behind Joan feeling her silky nightie under my fingers.

I awoke first my arm still around Joan, as I caressed her nightie. It had ridden up during the last part of the night. Slipping down further I could feel her arousal pressing against the front of her silky panties. She was laying on her back. Mmmm feels good enough to eat, I thought. Well why not. I slid down the bed and eased her hardness over the waistband. I first licked then kissed it. Exposing her purple head my lips sank down its length. Joan moaned. I quickly turned and lying on my side with my head resting on the inside of her thigh. Her panties around her hips I resumed my sucking. My own panties were in a similar position as was Joan’s head. We both were bobbing and sucking. Joan’s fingers were making their way to my rosebud opening. He slipped a finger inside me. I copied his movements.
“Mmmm, mmmm, mmmm.” I hummed.
“Mmmm, mmmm, mmmm, oooh. He responded.
Mine was actually “Mmmm, I’m going to cum.”
I think hers was “Mmmm I’m going to cum too.”
We exploded into each other’s mouths and quickly swallowed ready for the next load. Which soon followed. Both once again spent laying back in a post euphoric state. We heard more conversation from the next room.
‘Hey big boy, let me suck your cock and swallow your spunk before you go.”
This was followed by several moans finished with a satisfied aah.
Then ‘bye lover, ring me when you’re this way again’.
We heard the door close.
Joan and I spoke in hushed tones. I asked her how she knew I cross dressed.
She replied, “I could see the marks of your bra straps on your shoulders when you took your shirt off. Curious, I sneaked a look in your briefcase and saw the panties and bra, also a fresh unopened pair of sheer stockings. SORRY FOR SNEAKING.”
“I’m glad you did, I’ve had a wonderful night.” I answered. “But now I really need to get going, my company’s sexy lingerie doesn’t sell itself, you know”, I smiled.
After getting dressed with our male clothes covering our lingerie we left the room. In the dining room we discussed the previous night in hushed tones.
Then I dropped a bombshell on Paul. I told him that Jock [his father-in-law] and I had been panty lovers for years. As I have a never-ending supply of expensive and sexy lingerie, we have a weekly session at my business office where we dress up in bras, panties, suspenders belts, stockings [and sometimes skirts and blouses depending on our whim] and basically fuck each other senseless. The glazed underwear from our copious cumming is then laundered professionally and then issued in our “Factory Seconds” line. Some of those pre-glazed panties and bras find their way via Jock into Joan’s wardrobe; she has become a big fan of my company’s lingerie.
“Do you mean that Joan wears underwear that you and Jock have covered with your cum? That’s an incredible turn-on”.
“Do you like Joan’s underwear”, I asked?
“Oh Bill, I wear a pair of her panties any time that I can but I have never had the opportunity to glaze her panties even though I often want to”. I had noticed that she has a wonderful collection of sexy lingerie, especially for a mature woman of her age.”
“Well here’s a wonderful idea. The next panty session I have with Jock [or Jacqui] why don’t you come along too?”
“Oh I’m not sure how I’d feel about doing what we just did with my FiL”
“Trust me, Pete, once you see his lovely little sissycock encased in a sexy pair of black nylon panties, you’ll change you mind in a heartbeat”
“OK then, count me in”.
Bill looked at me, “You just came there didn’t you?”
“Yes, I couldn’t contain myself”.
“Let me lick your cum off the panties and then let me present you with your first [and it won’t be the last] pair of my company’s panties, panty-liner attached. What colour do you prefer?
We headed into the hotel bathroom.

Some of the text has been borrowed (with permission) from a story {Black Friday 1} by hottvcarole

The day following my initiation to Jo’s panties, I went into town with Jk, my girlfriend’s father. We had previously arranged that I would go for the day to the university library which was in the same street as his office, so it made sense for me to travel in with him.
I hadn’t spent much time on my own with Jk before so I hardly knew him. He was now around 50, losing his hair a bit, but in quite good shape physically.
We made small talk. At one point my eyes glanced between his legs - I was not in the habit of doing this and I still to this day have no idea why I did so - and I couldn’t fail to notice that he had a huge erection, his cock tenting his suit trousers. I looked away hurriedly but I am sure Jk saw me looking and I am also sure he smiled momentarily. Anyway, we reached the library, I gathered my things, got out the car, and Jk drove off.

At lunchtime as previously agreed we met outside a nearby hotel where we were going to have lunch. To my surprise we walked through the lobby, into the lift, and into a room on the second floor. When we entered the room I was intrigued to see quite a lot of technical equipment on the table. Jk was financial accountant for a computer video company and I assumed he had some equipment there to demonstrate to customers or potential employees. Boy how wrong I was…

“Peter” Jk said once we were inside and settled, “you’ve been a very naughty boy, haven’t you?”
I started to sweat immediately, surely he couldn’t know anything about my escapade yesterday with J’s panties, could he?
“Take a look at this, if you don’t mind”. He pressed a button on one of the machines and a film started to play on a monitor in the middle of the table.
You could plainly see me borrowing Js panties, putting them on, then my wanking session in the bathroom. I felt like I had been punched in the gut.
“Our company produces small cameras that can be used for surveillance, and we have installed a few in our house. Can you explain yourself?”
“ Oh I’m so desperately sorry, I was just so turned on by your wife and in a moment of madness I grabbed a pair of her panties because she excites me so much”.
“Whatever. You’re not the first and won’t be the last. Her slutty enormous tits do have that effect on young men. I’m afraid I’m going to have to show this film to the police. They’ll take a dim view of this sort of behaviour, and you might end up getting thrown out of Uni, maybe worse…”
“Oh no, please don’t do that. If I promise never to do that again will you let me off?”
“Well there is one solution, if you want to stay out of the hands of the law.”
“Oh anything, anything, please yes, what is it?”.
“Well you can become a pantied sissy for me. If you agree to that I’ll destroy the evidence and I’ll not tell my wife and daughter”.
I had no idea then what a pantied sissy was. I asked for some clarification.
“There are many men - like myself - who no longer get enough satisfaction from their wives. So they get sexual satisfaction from pantied sissies, subservient men who wear bras and panties and who make themselves available to older and stronger men. I’d expect you to wear Jo’s bras and panties for me on occasions and I would get you to suck my cock and let me shove it up your sissy arse. Do you think you could deal with that?”
I was horrified.”Oh no, I wouldn’t like that at all. Surely there’s another way out of this?”
“Not really, my pantied princess”, JK said “unless of course you fancy going down the police and courts route?”
When he put it like that, I could see I had no real option.
“How would it work then?”
Jk could see I was hooked. He told me to undress, and he passed a package to me.
“A set of Jo’s bra and panties, put them on now; I suspect you’ll spend a lot of time from now on dressed in her lingerie.”
I turned red with embarrassment, but got dressed as requested. I noticed my cock was harder than it had ever been, encased as it was in a lovely sexy pair of white lacy panties. I had never worn a bra before and I noticed with excitement that my nipples were growing erect where they brushed against the lacy cups of the white bra. I noticed that pre-cum was gushing from my cock-end and dampening the panties.
Jk knelt down in front of me and licked my cock through the damp panties.
“Quite a small cock but I have little use for that anyway.”
Jk stood up, took all his clothes off, i noticed he was dressed identically to me. His cock was also pressing against the panties front but way way higher than mine in fact his cock-head was popping out over the pantie elastic. “Suck my cock”, he barked.
Knowing arguing was pointless i knelt in front of jk’s pantied cock and kissed the panties, feeling the heat of his cock.
“I meant my cock, pull the panties down, you sissy”
I slowly pulled the panties down and placed my mouth over his huge bell-end. I wasn’t sure I’d get it in my mouth. As for his balls, they were massive, like two tennis balls. I had never been so close to another man’s balls, but I was longing to kiss them. I tentatively took his huge mushroom head into my sissy mouth. It tasted wonderful.
“OK, now you’ve got my cock lubricated, its time for me to take your sissy virginity. Lie back on the bed with your legs apart.”
“Oh Jack, I said, frightened. There’s no way you’ll get that huge thing inside me.”
Jack looked at me, evilly.
“That cock will go exactly where I want it to go, sonny. It’s impaled smaller and younger sissies than you, you know.
Lie down. This is going to hurt, then it’s really going to hurt, and then you’ll love it.”
Jk expertly lubed my bottom with 2 fingers that he spat on ( it did hurt) then slowly but masterfully inserted his huge erect cock inside me (which really hurt, so much it made me weep). He then turned me over onto my back. As he thrusted, I could see my tummy bulge as his huge cock reached it deepest stroke inside my sissyarse.
I had never seen that before and I was mesmerized. Within 5 strokes I came, the best cum I had ever experienced, gushing all over the front of Jo’s panties, glazing them with my sissycum for the first time ever. I knew it wouldn’t be the last time.
5 thrusts later Jack impregnated me with his mancum and as he came he shouted: ”Another sissyarse virginity taken! Get used to this cos from now on you are my sissy. Pull up your panties, and lie next to me.”
I lay there for a few seconds, realizing how my life had changed.
Slowly Jack’s cum started to drip out of my arse into my sissy panties. Now they were glazed front and back. I wondered what Jo would say when she got her panties back.
“These are your panties now, son. Keep them laundered, and wear them every time you are with me. You’ll get other bras and panties and blouses and skirts as time goes by but you might want to keep this set as a reminder of that day you became a sissy, or rather MY sissy.”
“What will Jo say, won’t she miss the panties?”
“Oh she’s used to me taking her underwear for my coven of sissies. I always buy her replacement lingerie so she’s never short. Basically that’s all she is for me now, a warm body for my sissies underwear.”
“Oh don’t you make love to her any more?”
Jack laughed. “She doesn’t suck cock, she won’t let me fuck her arse, what would I make love to her for?”
When he put it like that I could see why he preferred sissies, no sissy would ever refuse to suck his monstrous cock and balls, and would happily take his cock up their stretched sissy arse any time he demanded it. I couldn’t wait for a second chance of that.
I realised how safe I felt, being ordered around by this big strong masculine man, hanging onto his every word. I realized that I wanted to be his sissy for life, giving him pleasure in whatever way he wanted it.

I have known my Mother-in-law {Jo} for over 40 years now. From the first time I, as a 20-year-old, saw her, I wanted her. She was a voluptuous woman in her mid-forties and I was immediately fascinated by her breasts. From under her blouses it was clear that they were large and round, and I so wanted to see them for real. I used to take every opportunity to look at them, trying desperately to get a sight of some cleavage, or a bra strap even a bra-line through her blouse would make me instantly erect. I would often masturbate fantasising that I was kissing and fondling her breasts, tweaking her erect nipples, or shooting my cum over her bra-encased breasts. Over time I began to fantasise as much about her bras and panties as about her, and with time the lines between woman and underwear became blurred.
One summer’s day when I was staying at my girlfriend’s house I got an opportunity to take my fantasy one step further. My GF was out working, as was her father, Jack. Jo was in the garden and I was supposedly reading my books studying for an exam. From my room I could look onto the back garden and Jo looked very busy with her gardening tasks. Suddenly a crazy thought came into my head. Jo and Jack’s bedroom was the room next to where I was studying. I had an impulse to go into their room and look around to see if I could examine Jo’s underwear. Suddenly I was no longer in charge of what I was doing. I took a last look outside to check Jo was still busy, and my cock grew even more erect as I noticed she was at the bottom of the garden looking fully occupied. In a flash I was in their bedroom totally ignoring any chance of being caught. I didn’t really know what I was after; it was like I was in automatic mode. I crept over to the chest of drawers making sure I couldn’t be seen through the bedroom window. Silently I pulled each drawer open until BINGO! I found one that was full of lovely sexy bras and panties. I just grabbed the first pair of panties which took my fancy, closed the drawer, and crept back into my bedroom. I examined my prize, not realising that this was the first in a long line of Jo’s panties that I would hold in my trembling hands. They were white nylon, size 16, with lots of lace along the top and on the legs. My cock was sore from its erectness. Suddenly I knew I had to put them on. I went into the bathroom along the corridor, locked the door, got out of my clothes as quickly as possible and stood there naked in front of the mirror. My young cock had never been so rock-hard. Slowly I stepped into the panties and pulled them up over my cock and balls. I was amazed how it all felt, my balls were cupped tightly inside the wispy material and my huge erect cock was held in by the lovely nylon tightness. For the first time in my life I saw pre-cum, a tiny patch staining the front of Jo’s panties. That made me even harder.
Little did I know then that my life as a sissy, pantie-wearing crossdresser had begun.
I looked at my reflection in the mirror and admired my cock and balls encased in Jo’s wonderful panties. I pulled down the front of the panties and started to wank myself slowly. I fantasied about Jo’s huge tits, I thought about how these panties would look on her, the material covering her cunt and arsehole. I thought about how pleasurable it would be to cum all over the front of the panties, but even then I realised that I would not be able to hide that mess from Jo, so it wasn’t actually a possibility. Within seconds I came furiously, massive ropes of cum shooting all over the tiled bathroom floor. Hurriedly I pulled the panties off, checking that the pre-cum stain was hardly noticeable. I cleaned up the floor, got dressed again and moved back into my bedroom. Jo was still at work at the back of the garden, so I popped back into their bedroom and replaced the panties in the underwear drawer. Little did I know how much a part of my life that underwear drawer and its contents would become. Making sure the panties were placed in exactly the position they had been in before I borrowed them - and how good I became at that over the years - I took a last lustful look at the drawer then closed it, then left the bedroom.
Now the fear overcame me. Would Jo notice that I had worn the panties? If I was discovered how would that impact my relationship with my GF? I promised to myself I would never take such a risk again.
The next day I broke that promise.