My second visit to Bill's

By kylie_kained

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Tags: crossdressing, bdsm, spanking, trans, anal, oral

Added: 11 Sep 2012 Views: 13052 Avg Score: 4.85

This is the second part of Picked up in the toilets.
Here I was waiting to meet Simon, I had turned up an hour early. God I was keen after the week before, I just wanted more of the same. My mind whirred over wondering how many cocks I would suck and whether Debbie would suck me again. Would she tie me up this time? I just couldn't wait.

Eventually Simon pulled up at the arranged place just like he said he would. I got into the car and we set off to the next town, back to Bill’s.

Simon asked with a wry smile, “Did you enjoy yourself last week?”

“Yes very much so!” I blushed, agreeing.

We drove on making small talk, eventually arriving outside of Bill’s home.

As we approached the front door, I suddenly remembered Debbie’s parting words to me that I would be back. She was right, I so wanted a repeat of what went on a week ago. Already my cock was starting to stiffen in my underwear.

Debbie answered the door greeting Simon with a kiss. She kissed me on the cheek and whispered in my ear,
 “I told you so, sissy. You just couldn't say no could you!”

Again I blushed.

“Go on through to Bill, Simon, while I help get Kylie ready.”

We went up to the bathroom as Simon disappeared. Once again I was showered and shaved before she got me back into that gorgeous school uniform. Everything was clean and ironed which felt good. Debbie styled my hair and applied my makeup. I glanced in the mirror seeing myself once again. My cock was rising in anticipation of what was to come.

We went down to meet the others, me leading the way and feeling full of confidence. The guys were sat in the same place as last time, but there was something new in the room.

A padded low bench was in the center of the room. My mind wondered what it was for.

Debbie said in an almost manly voice, “Over to the bench, sissy. It’s time for you to experience something new! Kneel on the floor with your body laying across the bench.”

I did as I was asked without question, my panties starting to tent. Quickly Debbie secured my arms to the front legs of the bench, then moved to the back parting my legs and securing them to the back of my legs. My head was just off the bench but my body was comfy.

“Look she’s getting horny, I think it’s time that I stopped that!” Debbie grinned.

She raised my skirt and lowered my panties. I tensed knowing that she was going to spank me.


I muffled a cry. This time she was really going to town each slap seemed harder than the last. Finally she stopped and I breathed some relief, my backside on fire.

“Did that hurt?” she asked.

“Y-Y-Yes!” I replied.

“Then I will kiss it better for you.”

Her tender kisses on my backside felt good, but she was right - my cock had gone soft. The guys were playing with themselves as they watched. I felt so proud that I was turning them on. I knew it wouldn’t be long before I would be sucking them again. I couldn’t wait!

As Debbie was kissing and licking my backside, her tongue started to probe my hole. I tried to tense but because of the bench I couldn’t push away from her. As her tongue went deeper inside me it felt good, again my cock was rising.

“Did I give you permission to get stiff sissy?” Debbie said in that stern voice.

“No I’m sorry but I can’t help it!”

Debbie was rubbing something into her hands as I glanced back. I felt her slide a finger right inside me.

"Agggh!" I shouted.

She didn’t seem to care as another finger entered inside me. At first it hurt so bad. I thought she had done it to make my cock go soft again, which it had.

Before long the constant pumping of her fingers into me got easier, even when she had managed to insert four. It soon became pleasure once more, my wayward cock was rising again.

“This just wont do Kylie, I told you before now you will have to be punished again.”

Her fingers were removed from my backside. I tensed once again in anticipation of another spanking. She walked away and then back again. Before I knew it she had secured a ball gag in my mouth. It was like a harness going over my head as well as pulling tight into my mouth. Now I was worried why she had gagged me. How could I suck cock with it in my mouth?

Out the corner of my eye, I noticed she had a cane in her hand. This time I really tensed as she teased my cock with it gently tapping my balls. What had I done? Was I really that stupid, having willingly allowed her to tie me to the bench? I could now see her on my left side, cane in hand and now rubbing it on my backside.


I bit down hard on the ball gag, but soon tried to scream in pain as each stroke got harder. The tears were now freely running down my face. With each stroke I could see her breasts jiggle with the force she was using. After what seemed like ages, She finally stopped and removed the gag. I was still crying uncontrollably, my backside was stinging so bad, I wanted to rub it better but couldn't.

At last I managed to stop crying, as I noticed Bill coming over. He took off the ball gag and stood in front of me holding his cock in his hand. I sucked it so willingly, I was like a girl possessed. Not wanting him to stop pumping, the taste of his pre cum tasting so good.

I could feel something pushing at the entrance to my backside. It opened to accommodate the intruder, gently at first before it pushed ever deeper. I was in heaven as it went deep inside me, I could feel something slapping my bum as it pumped in and out. It rammed in deep; I heard Debbie moan! There was a lot of pulsing before it was removed. I could feel so the cum dripping out of me.

Bill pulled out of my mouth, as Simon took over I didn't seem to care. I felt so good as I tasted Simon’s pre cum!

Bill walked past me, before I realized that Debbie was now at my side. I felt shocked, as I realized what she had done! From the corner of my eye, I could see that she had a cock and it was soaked. I realized she had just fucked me. My face went red with the thought! How did I not know that she was a he?

Again I felt something pushing at my backside. It entered without much resistance. Bill was now fucking me hard and I didn't care!

I tried to push back so he went deeper. He fucked me for what seemed like hours, before he shot his load deep inside me. Simon shot his cum down my throat at almost the same time!

“Now you’re a real sissy girl, Kylie,” giggled Debbie. She pulled up my panties as the cum was running out of me and untied me.

We all went over to a sofa and sat down together. Me next to Bill and Debbie next to Simon. I rubbed my backside feeling the welts. Bill started kissing me, exploring my mouth with his tongue. I felt so much like a girl! Debbie was kissing Simon at the same time, before we stopped and chatted all together.

“How do you feel Kylie? Is it nice being a girl?” Bill asked.

I went on to agree that I enjoyed it, for the first time without feeling guilty.

“Would you come to a party I’m having in two weeks time?” Bill asked.

Of course I soon agreed before Simon said he couldn't come.

“It will be an over night party!” Bill explained. “That’s if you can still come, I could pick you up from the station if want?”

I said that I would tell my parents that I was staying with a friend, as I agreed to be at the party. Even if Simon wouldn't be there. Debbie then took me to shower before it was time to leave. Simon and myself said our good byes, before we traveled back home, my backside so sore and a grin on my face. I knew that I would be back for so much more, they had me hooked into being their whore.