I suppose this is how it all started for me

by BillyBoy

6 Sep 2021 2450 readers Score 8.2 (12 votes) PDF Mobi ePub Txt


When I was younger, my sisters and her friends were real tired of me following them around all the time. I didn’t have any friends of my own so I tried to play with them, much to their displeasure. One hot summer day, I remember being irritating as usual, following the girls and their friends into their room and bugging them. One of the friends, who was also pissed I was around, suggested I be tied up to keep me under control. Then they could go to another room and play in peace.

They all grabbed me and pushed me down on the bed face first. I was only wearing swim shorts so I could feel each of their pretty hands on my bare skin. They held me down as someone wrapped my wrists together behind me with one leg of a pair of dirty white tights. My ankles were then tied together with the other leg of the tights. They pulled everything tightly together and there I was, hog tied lying on the bed. I suddenly realized my predicament, so I began to cry out for assistance.

One of the girls rolled up a pair of purple nylon panties and pushed them in my face, trying to get me to open my mouth so she could force them in and shut me up. I tried to keep my mouth closed so she reached down and pinched my nipple as hard as she could. She grabbed a big hand full and pulled at it like she was going to pull it off. When I opened my mouth to scream HEY! She pushed the panty in and laughed.

I immediately tried to push the panty out of my mouth so they found another pair of tights in the hamper and wrapped them around my face, tying them in the back, holding the panty gag in securely. Somehow they had positioned the soiled cotton patch in the crotch of the tights right in the middle of my mouth. I remember the taste of the slippery nylon panties, getting wetter from my mouth, and the cotton tights pushing everything in so deep. They were filling my mouth. I could only squirm against the tight nylon binds, and moan through the silky ball in my mouth.

Finally, one of the girls pulled a pair of white and pink panties over my head, covering my face completely with the front of them, again with the dirty cotton patch right in front of my nose and mouth. “That will hold the little shit for a while,” she said and they left. I could see through a leg hole in the panties, the pile of dirty panties and training bras they had dumped there from the hamper. My face was lying on some of them, silky little flat chest trainers with all sorts of tight stretchy straps and clasps. Tiny little silk and cotton panties, too, all dirty, crusty and wrinkled from being stuffed in the hamper.

After being tied with these soft silky things, I thought I wished maybe they had forced me to wear some of the panties and bras to humiliate me, too. Then maybe they might have pulled at my nipples again, and grabbed and pinched my skin, or even spanked me and laughed at me. Four sets of girls’ hands slapping and pinching me would have been so naughty. I would have tried to wiggle a hand around somehow and pull at their bikini bottoms, or had one of them drop a top by mistake. I could have had them all naked, and touching me…

For years later as I would jerk off, these were the thoughts that raced through my mind. Me, forced to wear girls underwear, bound and gagged and touched by pretty girls. Later I learned there were lots of guys who liked little boys in girls’ panties, too. So sometimes I would imagine being forced and manhandled by some strong guys. But the girl fantasy was the best. I would even tie myself up with their nylons, and wear their bras and panties as I jacked off. I’d steal them from the hampers, and gag myself with them like what had happened years before.

During one of my fantasy sessions, in walk a couple of my sister’s friends. They were both living at the local college. I was sitting up with my hands tied with nylons in front of me sliding my fingers up and down around my hard cock. I’d pulled on a pair of black control top pantyhose and was wearing a red C cup bra stuffed with panties. I had the matching pair of red silk panties hanging part way out of my gagged mouth.

I immediately tried to reach up to pull out the gag as I was standing, ready to run out the door. “I told you we would find him like this again!” Once more they all pushed me down on the bed and finished tying me up more securely. Slapping my ass and pinching me hard as they did. They wrapped more and more stockings and pantyhose around my arms, ankles and face, tying them all so tight I couldn’t move, or cry out, or see at all. When I was secure, they all laughed, and told me they had a surprise for my sissy little ass.

The girls all seemed to be moving away, out the door and gone, really, except for one. I heard the door close as the others said goodbye, and then lock. I cringed as I felt the pinch on my nipple, and a hand on my ass, sliding up under the pantyhose, and down between my cheeks. The pinching of one nipple, then the other continued as the other hand slipped deeper under the pantyhose, spreading my cheeks, tickling my little ass hole. I tried to mumble something but the panty gag I had put there was doing a fine job of quieting me. I just whined and tried to wiggle away, but couldn’t. Soon the fingers were gripping and fondling my chest, and the others were probing just into my tight little asshole.

A voice and warm breath whispered in my ear. “You like all of this, don’t you?” was the question. But this was not a cute young college girl’s voice. It sounded more like a guy. But there I was, caught red handed, dressed like a sissy boy, jerking off in a girl’s underwear like a twink. The fact that I had not noticed one of the girl’s friends was a guy, didn’t surprise me. I was in such a hurry - surprised there with my dick in my hand.

He asked again, and all I could do was nod yes. Apparently that was all the encouragement he needed, he dropped back behind me, pulled down the pantyhose and spread my cheeks with both hands. He slipped his warm wet tongue right into my little hole, wiggling and licking it as he did. I moaned “Oh Shit” through the gag, and tried to roll away, but with no success.

“You little sissy slut, you got me so hot in your pretty red underwear, all tied up and gagged like this. I want to fuck you all day and all night long.” With that I felt his long hard probing cock head slip just inside my wet virgin ass. He gripped my ass cheeks hard and spread them wide as he began to pump in and out just a little bit at a time.

He hesitated once, reached into his pocket and dripped some cold slippery lube down my crack and into my hole. I moaned and jerked as he reentered me and slid in further than before. Soon he was sliding in and out slapping my ass with one hand and feeling my chest up with the other. When he came I didn’t think my ass could hold his huge cock and the load, too.

My ass dribbled cum for a long time after he left. I was helpless there, tied and gagged and violated. He told me he would be back in a couple of hours and we would try some new games. He told me he wanted to see me suck his big cock, and watch my face as he squirted cum in my mouth and all over my face and cute red bra. He told me he would teach me to be a good little cock whore for him, and some of his friends, and that I would like it.

I untied myself before he came back. I’m too embarrassed to talk to the girls any more. I haven’t found out who the guy was either. I still dress up pretty and jerk off, but now I have a new experience to think about when I do.

by BillyBoy

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