The Missing Story Series- Baseball
I answered a local Yahoo ad, for a top looking for a bottom Cross dresser. He had a large toy collection, but I was not sure if he meant size or number of playthings. Also he stated he wanted a CD to treat like a true woman 'bitch'. I was also not sure what that meant, but agreed to meet at the local bar.
I was a little disappointed because he was heavy and that turns me off. Also because Im only 133 pounds and hate to get squished. I was dressed to kill, and passable in my short red dress, hi heels, my brown wig, lipstick and hose. He ordered us beers and he told me his name was Tom, then began explaining about his toy collection. I have all kinds and sizes from small plugs to huge ass ripping BAM dildos, 13" long and 3" thick. I also like vegetables , cucumbers and zucchini, I told him zucchinis are a little extreme, but he insisted with time and stretching of my asshole that I can take one. I shrugged and forgot about it.
He was going on and on about his sex fantasies with CD's. How he'd love to get them naked on there back and use his toys on there asshole. He explained about his favorite gay video where a cross dresser gets fucked with a baseball bat screaming the whole time as its ruining him.. It sounded very hot and I wanted him to show it too me, not realizing in hindsight that he wanted to do that to me.
So we drank up and drove to his place, then right to the bedroom, He asked me to take my dress off only and bend over the chair with my heels on, so he can see his new pussy. I did and he spread my ass cheeks, 'Ahhh nice and shaved, and began rimming my hole, sending shivers down my spine.
He stopped and lubed his finger then immediately starting probing my asshole "Ahh your nice, lets loosen you up" inserting all 3 digits, rotating in circular motion as I cried aloud. "mmmm I like that' I said. Let me slide this plug in you and I'll show my collection in the basement. I've been fucked a lot, so a small plug was easy to take, as he patted me on the bottom and lead me to the basement. The basement was clean but dark, The one wall had a sling and some other bondage instruments and a wall with shelves covered with dongs of various sizes. He explained them all. He told me to wait and then appeared with some vegetables, cucumbers and zucchini. On the floor I saw several large round cylinders of plastic each shaped for insertion, but the where much to big to fit in an asshole, Indeed the size of small baseball bats, and finally some plastic wiffle ball bats, small children's models and a full size bat, then the over sized plastic softball bats with 4 inch barrels.
What I like to do is work your honey asshole in my sling with my toys, get you nice and loose while you watch gay anal videos, getting you ready to get really opened up and then take some pix with that bat up your honey ass!", I agreed sounds like fun but no bat, you can use your large dongs, but my asshole would split open taking a bat deep at 4 inches width.
He was disappointed but agreed.
"Go jump in the shower, clean up and we can start by shaving your big asshole, Oh by the way, leave the plug in". The shower was hot and only intensifies the alcohol. I stepped out of the steamy shower, to be greeted by Tom razor in one hand, shaving cream in the other. "bend over this chair, lets make you silky smooth". I bent over, as he kneeled behind me, setting the razor and cream on the floor, he pulled my ass cheeks apart revealing the planted plug. He grabbed the flanged end with his teeth and pulled. It came out with a pop!, the he proceeded to apply the cream to my bottom and upper thighs. Slowely he shaved my ass, balls and upper thighs until the were smooth, then with a sharp SLAP on the bottom I was free. "OK lets get down to business, Hop up in that sling and lets get those femmy legs high in the air!" he said.
I slipped my hi heels and climbed into the sling, while Tom went to his wall of toys choosing what seemed to be a 6" vibrator and lubed it,. As he approached I grabbed my ankles and exposed my shaved fuckhole to him. He approached, my hole, waist level to him, perfect position to use his toys and me, and get a good look at them as he would play. "oh honey, this is sooo hot" he said, then held my knee and slide the vibrator right in. Ohhh I said, its warm!", "its self heating" then he flipped the switch as it started buzzing in me" oooohhh oh yes!, I like this" I said.. His face got real close to my opening that was vibrating like crazy as he licked my filled hole. "mmm I like too" Tom replied.
You took that easily, lets go to shelf number two. He walked away, vibrator planted to the hilt buzzing away as I closed my eyes and enjoyed the feeling.
He came back with a much larger dong, non vibrating type and fat too. He pulled the vibrator out, turned it off, the began to push the 9" thick dong in, It was wide so he pushed harder, "Comon' bitch open up", the rubber head slid into me stretching my asshole , "oh god , yes!" i said as i accepted the head, then quickly he pushed the rest in. "Unghhhh, oh your rough!" slow down. "ok, now that its in lets work this guy, I love to see ass lips move in and out" He pulled it out almost all the way, just enough for my ass to feel the widest part of the head, then drove it back in, " Oh yes, loosen my asshole good". He began working it like I was getting fucked, rough and fast. The sling was swinging with each thrust as a grunted and groaned to accept his fast paced action. "oh, you loosen up nice", with a big thrust, causing me to whimper.. "I like to see that cucumber slide in your hole and really get you loose. He continue and planted the dong to the hilt and said " I need my sluts bound and gagged" I did not reply, as I was in ecstasy, willing to submit to his needs. He grabbed some rope and tied each wrist to the sling support ropes.
"Oh honey, this eggplant is wider than the dong planted in your sweet asshole" He raised the purple end to my now loose hole and pushed the fat end in first, the 3 inch width split my ring and sunk in and as he continued to push, the eggplant became smaller and sucked the whole thing into my rectum. It was the widest its been that night, "Ohhh my asss, your really stretching my hole, Ohhhh gawd" I moaned. "oh so hot, as he pushed more the widest part came close then my ass could not stretch any wider. "that’s it, I can take any more" I said. He quickly pulled it out and said " Lets try again. He pushed the eggplant in and with pressure slid that thing deep in my as just past its widest part "Ooooh ive never been this opened" I said, " I'm filled! " "yes, its so hot, lets just keep it there, and get that hole gaping wide. He left and return with the wiffle bat "no no, please it tooo big" I screamed. No bitch, look at the eggplant buried in your ass, its just as wide, only longer", I beg and whimpered as he greased the fat plastic bat end. He grabbed the eggplant and pulled, It quickly escaped my ass, from the incredible pressure of my overstreched asshole.
He pushed the fat bat end at my hole, It dented my anal ring, but was to fat to take all at once. With both hands on the handle and one hand holding the sling he pushed again, my loose hole opened up as I screamed from its width the bat end went in and he stopped, " lets hold it there, give you a good rectal stretching, then Im going to pile drive it in you." he said
The bat stretched my ass so loose.. as he dropped his pants and began jacking his own cock. " Oh honey, your wide open, now take this you slut, and pushed the bat further in my ass, I watched as it sunk a good 8" and threw back my head and screamed, "OOOHHHH GAWD!, THAT’S IT RUIN ME", he slide that bat in and out a couple of time each time driving it a little deep until I almost passed out , I looked down to see him working a good 9 " in then out of my ass while, the sling was swinging, as I was screaming form the deepest widest thing I've ever taken , this set him off as he shot a big load all over me.
Oh that’s what I needed, sliding the bat out, my asshole was mincemeat , all red and wide open, "I like this".. He unhooked me and I got out.