Janets Sissy

By Rick 4u

Published on Mar 22, 2020

Transgender

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When they were all spent, I went around cleaning each cock again with my mouth, then they all left the room. I was ordered to clean the cum out of both their pussies, when I was done, they had me lay on the bed and they took all 12 used condoms and one by one put the opened end in my mouth and squeezed out all the cum from each of them making me swallow all of it.

This was only the first day there, we had 6 day's to go and I could only imagine what the rest of the vacation would bring.

Chapter 8

The following day after cleaning my ass, showering, getting my cage and plug reinserted and drinking the girls morning piss, I was brought into the bathroom and made to sit on a pile of tiles on the floor with my back up against the toilet, they bought some rope and tied my hands behind me and around the base of the toilet and tied my feet together, Janet said "we're going to the beach now, you may have some visitors while we are gone". They gathered all their valuables and suitcases and locked them in the security closet leaving me there naked and tied to the toilet. I heard them leave the room and began wondering what was going on and what visitors?

Within a few minutes I heard the door open and I heard someone enter, at the doorway stood one of the maids, she was a huge black woman, she just looked at me and smiled and went about her business cleaning up the room, she got to the bathroom and cleaned the tub and sink, put new towels on the racks and left again, never saying a word to me, she came back in and said "you're mistresses told me you were in here and that if I had to use the bathroom I could use your mouth", now lay your head back cause I really have to go". She lifted her skirt and pulled her panties down and sat her pussy right onto my open mouth, her huge body engulfed my entire head and could hardly breath, then her warm pee started flowing into my mouth, I tried swallowing as much as I could as it poured into my mouth, I was gasping for air as she pissed. She finally finished and wiped her pussy over my mouth saying "clean it up". She got off me and left the room.

A short time later i heard someone enter again, this time it was a man who appeared to be around 50, he walked in took his foot and pushed it against my cock squishing my cage against it, then he pulled out his cock and shoved it in my mouth, I greedily sucked it, then he pulled it out and jacked off till his cum sprayed my face, he pulled his pants up and said "see you later faggot" and left. A few minutes went by and another guy entered, he was about 400lbs he dropped his bathing suit to reveal a cock that was about 2 inches long, he lifted his gut and rested it on my head and shoved his tiny cock in my mouth, within seconds he pulled out and shot his load on my face, he left and another guy entered the room, he was around 25 and had a huge 10"cock, he shoved in my mouth as I began sucking it, he too pulled out and jacked off till a huge load shot across my face hitting myself forehead and running down my face. The next 5 hours guy after guy every shape and size entered the room, pulled their cocks out and face fucked me then shot their loads on my face, some of them made comments like "suck it good faggot", a few played with my cage, pulling on it, checking it out, some squeezed my balls or stepped on them, crushing them. All in all I think I sucked at least 30 or 40 cocks while I sat there, I had cum dripping from my hair, my face, all over my body, I was literally cum covered. When the girls returned they walked in and said "we see you had some visitors today, we told every guy we could find on the beach where to find you". They then began scooping up large gobs of cum and began feeding it to me, they used a glass to scoop it up and poured it into my mouth, I swallowed every drop of it. Cheri said "I think he liked it, his tiny clit is leaking precum like a fountain"

Later that evening after we had dinner, we sat out by the pool, I sat on the ground between Janet and Cheri, all of us naked, I noticed several guys who I sucked off earlier in the day, some of them walked by and told the girls wha a good cocksucker I was, the girls told them "same time tomorrow, he'll be sucking again". An old man in his seventies approached us, I recognized him from earlier in the day and I recognized his long shriveled cock. The man said "hi girls, I'm Tom, you're sissy here sucked me off today and I was wondering if we could rent him for a few hours tonight, we're here with 3 other couples and we'd love to use him for a few hours" Cheri said you can take him rent free! He then asked "does he eat pussy too"? She said "he'll eat anything you put in his mouth, and he'll do anything you tell him, right slave?" Yes ma'am I replied. Cheri handed him my leash and said "there's a butt plug up his ass, just take it out if you need access to it" He took my leash and led me away. We arrived to his room and he led me in, his wife was there, she too was in her seventies, she was completely naked like her husband, she had large sagging breast that were hanging down on her stomach and a shriveled ass and body, she sat in a chair and he walked me over to her, she began playing with my caged cock and squeezed my balls, she then pulled me closer and began licking my cock through the openings in the cage and licked my swollen balls. Come over here Tom, I want to see him suck your dick" he walked over and put his shriveled cock In my mouth, I began sucking it and it began to harden in my mouth, there was a knock I the door and the other 3 couples walked in, they were all in their late seventies or early eighties, all naked and all with aged sagging bodies, I continued sucking Tom's cock and the others gathered around me to watch, Toms wife sat on the chair in front of me and told me to eat her pussy from behind, I looked at her sagging ass and sagging pussy lips and knew I didn't have a choice, I took my hands and spread her open and found her old pussy and began licking it,, Tom pulled out my buttplug and lubed my asshole and pushed his semi erect cock into it, two other men stood on each side of Tom's wife and she took their limp cocks and began stroking them, the other 3 women went down on the last old man, he was an old black man, his cock hung down close to his knees, Toms wife then pulled the two men's cocks in front of my mouth and told me to suck both of them, I had a cock up my ass and two in my mouth, I slurped at both cocks, then I could feel the cum shooting in my ass. The black man then replaced Toms cock in my ass and it felt like it was hitting my stomach with every stroke, another woman replaced Toms wife and I began eating her , sagging pussy, the other 2 men started fucking the other two women on the bed, the black guy pulled out of me and pushed me aside and shoved his cock into the pussy I was eating. He came after a few minutes and told me to get back in there a lock her pussy again, I licked her pussy lapping up the guys cum from her. The other 2 guys took turns fucking my ass while I licked each women's pussies till they all orgasmed. When they were done Tom put my butt plug back in and took me back to my room and thanked Cheri at the door, Cheri walked me in and there were 2 men laying on the bed, Cheri walked me next to the bed and she climbed in next to Janet and spread her legs, I could tell they just got done fucking because the guys cocks were wet with pussy juice and cum dripping from the heads and the girls pussies were leaking cum, I recognized the 2 guys who were among the six who I sucked and got fucked By a few days before. Janet ordered me to get up here and clean all of them up, I started with the first guy and took his limp cock into my mouth and cleaned up the cum and pussy juice from it, then I moved to Janet and licked the juices from her pussy, then CherI and finally the last guy, the 2 guys got up and left and the 2 girls turned over and said they both needed a nice rim job, I climbed between Janets legs and rimmed her then rimmed Cheri, when they had enough they got up, and I got up to clean up, Cheri said "we really need to do something about that cock of his, it's got a constant drip going on from that cage." Janet said, Well it's only been about 10 weeks since he came, but I suppose we can let him shoot a load", she unlocked my cock, but left the base ring on, my cock rose to attention with precum oozing out of the head. Cheri said "it's to small to fuck and to small to suck" Janet said "he can make himself cum by jacking off" she pulled the plug out of my ass and inserted the vibrating prostrate massager, she then climbed up and sat on my face and said go ahead and jack yourself off, I started stroking my cock slowly, it felt so good I wanted it to last, I used my precum as a lube for my hand, Janet fronded her pussy into my face, still getting little taste of cum as I did so, I couldn't hold back any longer and started stroking faster, I was afraid any second they would stop me and leave me in agony again, then before I knew it the cum shot out of me and sprayed all over my stomach chest and on Janet, it felt amazing, it was the hardest I ever came. When I was done they scooped up my cum and fed it to me, then I was told to get on the floor and go to sleep.

Next: Chapter 9


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