tagTranssexuals & CrossdressersHow Low Can You Go?

How Low Can You Go?


Be careful what you wish for; that's a popular phrase in these Literotica stories. I found out the hard way the import of this message.

I have always had a submissive streak a mile wide, but in my twenty-eight years I'd never experienced the feeling of completely surrendering to another person. With the Internet and its free personals web sites, I decided that it was now or never, so I answered some ads and submitted a few of my own.

I quickly learned to read between the lines of an email. First of all, not one of the women I contacted was truly dominant; they were looking for money. The second thing, there are lots of horny men out there just looking to give or receive a blowjob. I think many of these answered my ads because they were inexperienced and figured that a submissive was a safe bet. In their ignorance, they weren't aware the vast difference between fantasy and reality.

Most of the men who answered were married. I never wanted to be "the other woman" or in my case, "the other man." Nevertheless, I wasn't getting any younger, so I decided that it wasn't me who was cheating, and these "bears," as they called themselves, seemed to know exactly what they wanted.

I answered several ads until I found an older man who wanted me to come to his house. It seemed the safest way to meet a dominant stranger. After all, he couldn't do anything harmful or illegal, because I knew where he lived.

Long story short, he proved to be exactly what I needed. He wasn't into props or endless dialog, he wanted to use me, and that he did. His cock was intimidating, not very long considering the size of the plum shaped head and its girth. My god, I thought to myself, it looks like a saddle horn! I think I could have taken it in my mouth if I could maneuver into the right position, but he handled me like a rag doll. He finally picked up my slender frame and carried me to the bedroom. He left me on the bed on my knees with legs spread and face pressed against the bedspread. While I waited, I could see myself in the closet door mirror. Not bad, I thought to myself, I'd fuck that in a heartbeat.

It never occurred to me that he would fuck me on our first visit, but the next thing I knew was an excruciating pain in my ass. I howled and the pain stopped. I was still reeling from the invasion when I realized that his cock was buried to the hilt up my butt hole. I was amazed that the pain was gone, just a feeling so intense that I haven't the words to describe the sensation as he sawed his fat cock in and out of my ass. I could feel my sphincter grip his shaft; I could feel it stretching, clinging, not wanting to let it go but at the same time automatically trying to rid itself from the intruder.

I was moaning and babbling incoherently when I felt the hot jets of cum as he sprayed my back and ass with his semen. He reached under me and grabbed my rigid cock. It took only a few strokes before I filled his hand with my own cum. He grabbed my hair and tilted my head back. He then placed his cum soaked hand and smeared my semen over my face, forcing me to lick his hand clean. I was still trying to catch my breath when I realized he'd left the room.

I was disappointed when he returned with his clothes on. He handed me my own clothes and told me to get dressed. I thanked him and asked if we could get together soon. He was willing, but his time was limited. I had come to expect that all dominant married men are pussywhipped. That's probably why they need someone like me to follow their orders for a change. I offered to pay for a hotel room near his house some Saturday night and he could come over when he could get away from the missus. He offered to pay for the second day so we would have the entire weekend. The three star hotel was very nice, with a king sized bed and a spacious entertainment area with a couch, large comfortable chairs and a big screen TV. We picked a weekend and I went home and made the reservation. The wait seemed endless.

While I waited for my new master, I received many emails from him full of special requests and orders. I've never been into cross dressing, but he demanded that I purchase some lingerie to model for him. I was too embarrassed to go to the stores, so I bought a baby doll pajamas top on the Internet and included a pair of pink lace panties. I also purchased a white lace bra and matching panties. It took hours of searching to find a bra my size with an A cup and no underwire. I found that I was correct about the cup size. The petite little thing looked much better than if it was stuffed or padded. I bought a denim mini skirt and peasant blouse. I even made an appointment to have my long hair cut. I wanted something I could style with a hot comb yet still comb it straight and appropriate for everyday wear. I emailed him back and told him what I'd purchased and warned him that although I have a slender, feminine body, no one would believe that I was a woman. He wrote back and told me that I wasn't a woman. He told me I was a sissy and he was sure I looked the part in my new frilly clothes.

I arrived at the hotel Saturday afternoon and stripped naked as he'd ordered. I sat on the floor near the door and waited. It wasn't long before I heard his key card swiping the hotel room door. As ordered, I spread my legs and lowered my head to the floor. He hadn't said a word; I was following the orders I'd been receiving in his emails. I untied his shoes and removed them along with his socks. I couldn't bear to look at his face as I undid his fly and lowered his pants and boxers. His fat cock bounced lewdly in front of me.

Try as I may, I just couldn't fit his cock in my mouth, so I licked and kissed the head as best I could. He grew impatient and turned around. He spread his ass and I knew what he wanted. I struggled to keep my balance without using my hands while I worshipped his asshole. I swirled my tongue around his anus, finally darting the tip of my tongue inside. He reached around and grabbed the back of my head. I stuck out my tongue as far as possible and held it rigid as he forced my head to bob back and forth, tongue fucking his ass with an occasional pause for me to lap at the saliva that dripped from my chin and onto his large sweaty balls.

He picked me up and stood behind me. He bent me over at the waist and spread my legs wide with his feet. Just as before, the pain was intense but momentary. He knew precisely how to slide his big fat cock up my ass. I couldn't miss the irony. While he bent me over and fucked me right in the middle of the spacious room, I thought of the money we spent for the king sized bed and leather furniture and how we were using none of those things.

He fucked me that way for several minutes. Long before he was ready to cum, he had me bent over with his left arm holding me around the waist while his right reached under me and used his forearm to press me against his chest. He was humping me like I was a bitch in heat when he finally groaned and removed his cock, once again spraying copious jets of hot semen across my back.

He sent me to the bathroom to shower and get ready for bed. I dressed in my baby doll pajamas. I took a deep breath and entered the room for his inspection. He seemed pleased with my outfit. I knew that he wanted a naive sissy rather than a slutty crossdresser, so I'd opted for a pastel cotton print top with an empire waist that flared nicely from my flat chest and left the bottom half of my pretty little lace panties exposed. I'd included a pair of loose fitting, hot pink shorts. He had me model for him, swaying my hips while I walked about the room. My thoughts ranged from pleasing him to the humiliation of dressing up like a sissy and prancing around for his pleasure.

Without warning, he told me to take the little plastic bucket and go fetch some ice for his drink. I hurried down the hallway, hoping that no one would see me in my girly pajamas. I couldn't find an ice machine so I hurried back to the room and faced my new master with an empty bucket

He was livid; saying that I wasn't gone long enough to find the ice machine. He took me by the hand and led me out the door. I could feel the eyes on me as he dragged me up and down every hallway until we finally discovered the ice machine. To my dismay, three young women waited while I filled the bucket. They giggled when my master told me that my half hearted search for the ice machine had just earned me a spanking.

We were about to leave when one of the girls stopped us. She wanted to know if he was serious about giving me a spanking. He said without hesitation that I would soon be lying over his knee for some much needed discipline. The girls huddled together, whispering to each other. The one who had spoken asked if they could watch. He told them that as long as they were eighteen it would serve me right to have them witness my punishment.

My master warned me repeatedly in his emails to expect a sound spanking, but I never in my wildest dreams imagined that he would drag me around the hotel, let alone invite three pretty young ladies to witness a grown man's humiliation of being spanked like a naughty child over my master's knee.

And it was very humiliating. I had to wiggle my hips to slide out of the pink pajama bottoms. He placed one of the straight backed, armless chairs in the center of the entertainment area. The girls sat on the couch and giggled as I was placed over his knee. He delivered two sound swats and paused, asking the girls if I should have my panties down so that my spanking would be on my bare bottom. The girls replied unanimously and my panties were soon dangling on my ankles while he delivered a staccato of bare handed slaps to my upturned bottom. The louder I cried and pleaded for mercy, the louder the girls laughed at me. In fact, it was they who pleaded with my master to stop spanking me before they wet their pants from laughing so hard.

I stood beside him, my butt burning from the relentless swats to my tender bottom. As he scolded me, the girls were whispering together. Finally, they asked him if they could touch my penis. While I stood before each girl and allowed them to fondle me, they remarked on the diminutive size of my genitals. My penis was flaccid. This very real humiliation had won out over my desire to role-play as a submissive toy. I was finally allowed to stand in the corner and face the wall to hide my shame.

I stood in the corner for what seemed an eternity while he chatted with the girls. I heard him say that he'd like to go down to the bar for a drink and they asked if they could stay for a while longer. He told them to help themselves to the mini bar, adding that I was paying the bill. His last words as he left was to request that I remain standing in the corner until he returned. I stood there for at least an hour while they emptied the mini bar and discussed the scene they had just witnessed. When my master returned, he made me thank them for babysitting while he was away.

With the girls gone I was alone with my master. We spent the evening watching television. Actually, he watched TV while I sat on his lap facing him. He seemed to enjoy reaching under my nightie and feeling me up. He tweaked my nipples just enough to make them stiff and tender to his touch. My penis throbbed every time he patted my bottom. When the extended sports highlights came on the news, he told me to go to bed. He would join me later, he said.

I was sound asleep when I awoke to find him rolling over on top of me. We said nothing while he slid his cock up my ass. We lay together with his body pressing me to the bed. The only movement was his pelvis humping his cock up my asshole. He rode me bareback, filling my ass with his hot sticky load. He withdrew his cock and rolled off of me. I soon fell back into a sound sleep.

I awoke alone in bed the next morning. I found a plate of fruits and bagels on the coffee table along with a note telling me to get dressed for the day. I showered and shaved from top to bottom. I styled my hair and applied a little makeup. I left the bathroom wearing only my white lace bra and panties and opened my bag to remove the denim skirt and peasant blouse when I heard the card slide through the door lock.

The silence was broken by the men who charged into the room. They were boisterous, carrying sacks of beer and discussing the playoff games that were on that day. I relaxed a little when I saw that my master was with them. Nevertheless, I was terrified as I stood there in a room full of men while wearing only my makeup and bra and panties.

Suddenly, strong arms reached around from behind me and held me close to him. His hands roamed my body as he commented to my master that I was even more of a sissy than he'd described. To my surprise and horror, the man turned me around and pressed me up against the wall. He held me tightly, his mouth just inches away from my lipstick red lips. I watched his lips move as he told me that he was going to kiss me and if I knew what was good for me, I'd better return his kiss like a cheerleader on prom night.

Of all of the degrading, humiliating tasks I was made to perform that weekend, kissing this man was without a doubt the most puzzling task for me. I'd never been kissed by a man before, but the stubble of his beard and his tongue invading my mouth so forcefully had me seeing stars. I found to my dismay that my penis had grown stiff in my panties.

He stopped kissing me long enough to carry me over to the leather couch. He took me into his arms and reminded me that I was expected to return his kisses with enthusiasm. I'm ashamed to admit that I loved clinging to him, melting my near naked body against him and moaning softly as we made out like teenagers.

I had a hicky the size of a baseball when the man pushed me to the floor, where I laid in the center of the rug with the large screen television mounted on the wall behind me. I was ignored while the men talked and drank beer. They eventually settled into the leather couch and chairs to watch the two playoff games. The first quarter ended before my master called for me to crawl to him and suck his cock. Two of the other four guys were actually interested in the game, but the other pair roared with laughter as I tried in vain to fit my master's thick cock in my mouth. My master grew impatient and tired of the taunts coming from the man who'd been kissing me. He told me to crawl across the room and suck the man's cock. He was waiting for me in a leather recliner with his cock out and legs spread.

I was well aware of my predicament. I was helpless, at the mercy of my master's whim and his rowdy friends. Nevertheless, I was grateful for the opportunity to show my master my ability to suck cock. The man's cock wasn't nearly as fat as my master's, but it was almost twice the length. I lathered it with my tongue from his balls to its circumcised head. He pushed my head down and I surprised everyone by taking nearly ten inches of cock down my throat. Even the two guys trying to watch the game stopped to watch me sucking that big tool, taking it completely down my throat and then bobbing up and down. Sometimes, I allowed it to slip free with a loud sticky plop. My face grew wet from trying to get the slippery shaft back into my hungry mouth.

The man held the sides of my head and began fucking my face. He told me to say 'ah' which caused me to make lewd, guttural, gargling noises as he plunged his cock down my throat. In retrospect, I think he paused to take a rest; perhaps to keep him from cumming and prolong his blowjob. Once again, I amazed them all by using my throat to milk his cock. I was rewarded with a flow of hot semen that drained down my throat and straight into my sissy tummy. I spent the second quarter crawling from man to man, sucking their cocks and licking their balls. None of the other three cocks were nearly as big as my master's or the man I'd given a throat job, but they were all much bigger than my own. My jaws were aching by the time the gun went off for halftime. I lay on the floor as the men made sandwiches and discussed the game.

I was sucking one of the two guys who were intent on the game when the guy with the ten inches grabbed me and placed me on my hands and knees in the center of the rug. As my master settled into his easy chair, he saw the scene under the large screen and told the man that he wanted to see the game, not watch his sissy taking it up the ass. He told him to put me on the bed if he wanted to fuck me. The man grabbed a man-sized handful of the back of my panties and led me, duck walking on hands and feet with the crotch of my panties pulled tightly between my butt cheeks. The swats I received as I passed the other men burned like fire on my recently spanked bottom.

Truth be told, the man was trying to be gentle when he began to fuck me. He'd tossed me on the bed, ripping my panties off as he did. He grabbed my hips and positioned me with my knees spread and pulled me toward him until my ass was in line with his giant cock as he stood beside the bed.

Nevertheless, no amount of lotion or coaxing could keep me from crying out in pain. The man tried to ease the head of his cock past my sphincter muscle but I just couldn't stand it. Someone called out to tell me to shut the fuck up, so my master came to my rescue, all the while grumbling about missing the kickoff just to fuck me and silence my howling. Just as before, there was a sharp pain and then my master's cock was up my ass to the hilt. Just as before, I clawed at the bedspread and involuntarily humped my ass in an effort to rub his cock against that spot which makes my own cock turn stiff as a twig.

It was as if he knew exactly what I needed. He grasped my hips firmly and found my prostrate with his plum sized crown and laughed as I began humping furiously, fucking myself on his great horn of a cock. I blinked in surprise when a hot jet of my own semen hit me square on the face as he held me practically on my head and drained his cock down my asshole.

He didn't wipe my ass, but left me on the bed with my knees spread and semen already beginning to run down the inside of my thighs. He returned with some sort of harness that he attached to my head. He then produced a ball gag and, stuffing the ball in my mouth, attached it to the leather bridle. He cinched it tight and then attached a short leash to the ring on the top of the bridle. I felt the bed move and found one of the men sitting in front of me on the bed with a camera. He took several pictures and said that this was always his best picture when they fucked a sissy. He turned the digital camera so that I could see my face. I knew then what the photographer meant; my mouth was stretched lewdly over the red rubber ball with a long trail of saliva hanging from my chin, but it was my eyes that made the picture. There is no way to describe the look in my eyes as they balefully gazed between the leather straps which met at the bridge of my nose. My master waved the man with the camera away and told the man with the giant cock to enjoy himself before returning to his football game.

I doubt that the gag really helped, for all I did was whimper softly as the giant cock completed the trail my master had just blazed up my ass. He held my head up by the short leash in one hand while the other grabbed my butt cheek. He drove his rod into me time and time again. My own cock was soft, but my eyes exploded with silvery white lights as I swooned into a faint.

I remained in a surreal swoon throughout the rest of the football games. I was barely aware when one cock would slip from my asshole, only to be replaced by another. The guys with the smaller cocks compensated with skills the man with the big cock didn't need. They both found my prostrate easily, and I came several times as I was fucked until they all blended into one cock fucking me relentlessly, endlessly.

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byCompliant1© 0 comments/ 61636 views/ 9 favorites

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