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.