Sissy

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side.

(M+/M, oral, anal)

In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job.

In my second letter "Gloryhole Illustration" I describe how I accidentally discovered a glory hole and learned what they are used for.

In my third titled "Steely" I discover that there is a whole underground of men cruising for sex.

In my fourth letter "Zebulon" I tell you about a visit to an adult bookstore expecting to suck cock but getting more than I bargained for.

In this letter I tell you about how I use my experiences to explore my psyche and further define what I want in an MM relationship.

When I left the adult bookstore I had a lot of thinking to do. I went imagining I would suck some cock. As I have said before, I'm not gay but I am fascinated with cocks and I don't mind trading blowjobs. But the last time I hooked up with a guy several things changed. I had been dominated, fucked, double-teamed, treated like a sissy, and for me, worst of all, forced to interact with more of man's body than just his cock.

I reflected on the thoughts and feelings generated in me for several weeks. In the end, I arrived at several conclusions.

Why did I like being fucked? Maybe because being fucked is simply a physical sensation. My body reacted to pleasurable

feelings without regard for how they were generated.

Am I gay? Is this why I like serving men? No, I'm not gay. I am not equally attracted to men and women. I am only attracted to people with beautiful bodies, though I do have higher standards for men than for women. I don't like hairy, fat women any more than I like hairy, fat men. Men clearly have many more attributes (such as hairy armpits and beards) that make it easy to eliminate them from consideration as a lover. But as long as I can focus only on the aspects I appreciate, then I enjoy sex with either pretty women or handsome men. Given the choice of Tom Cruise or Rosie O'Donnell I would take Tom any day.

But why not just trade suck jobs? I guess as much as I tried to separate the act of cocksucking from the person, sex is always a part of a relationship.

Some men were more dynamic and forceful therefore able to create a relationship with me, even if it was just fucking my ass, dominant kind of relationship, when I otherwise might not have had anything to do with them.

I guess I included the more intense relationships in these letters in these letters because there was more emotional involvement than in the others. Even if the emotions were not always what I would want.

What is it about being forced to have sex and being submissive that turns me on? As I think about it being forced removes any personal responsibility on my part. As long as I am forced I can tell myself that I don't really choose to engage in same-sex behavior. But more important than that was that being forced let me loose control and experience the events however they happened to take place rather than trying to create them. If I had been in control over the last year I would never have experienced the things I did.

Lastly, I recognize in my fantasies some odd line of reasoning that if men have sex with me on their terms that they will like me. I think this goes back to my childhood when I wasn't very popular but some of my friendships consisted of being involved with a group of boys in regular circle jerks and sexual discovery.

The last piece of my psyche to uncover was the question of whether I was a sissy and what that meant. I think some of this question has already been answered but there seems to be more. I can't think of a reason that satisfies me as being the right answer.

That is why I have decided that to figure this puzzle out I need to indulge myself in this fantasy. When I submit to another as a complete submissive sissy I will have my answer.

Now the only conundrum I faced was how to become a sissy and submit? I had given this much thought. I knew I might be making a mistake but I went forward anyway.

I went back to the forest preserve to see my "friends" there. I asked around to see who might want to be a part of a relationship like that. Several guys told me that if I were brave enough I could find what I wanted from Steve.

Going back at the right time I looked for Steve who was suppose to drive a red jeep or Humvee. I found him the second day I looked.

Getting nervous I approached his car and struck up a conversation. Steve

struck me as an arrogant s.o.b. but after we talked a bit I steered the topic around a bit until he took the bait and invited me back to his house.

Steve lived in a huge two story Tudor which was intimidating in its size alone. We drove thru a set of large iron gates and entered into the foyer which was decorated in every way to make one feel small and insignificant.

Immediately after entering, Steve's demeanor changed. No longer just arrogant he was now bossy, rude, and demanding.

I started to think that I should just leave now as I really didn't enjoy being treated badly on a social level.

But I had to finish what I had started. Even if he treated my like crap I was told the sex would be good.

Steve turned to me and said "Strip!" That's it just one word. And it wasn't a request. Right there in the foyer I removed my clothes leaving them crumpled on the floor. I didn't know if anyone else was home. Would the maid come around the corner seeing me buck naked?

Steve beckoned with his finger and I followed him up the stairs as did two dobermans who appeared out of nowhere. Fear was building up to a high level now. I tried to shoo the dogs away from sniffing my ass but Steve just said to let them have their way and they would leave me alone - probably.

Steve led me to a master bedroom/bathroom where he instructed me to bathe, shave, and dress. He laid out some frilly clothes on the bed and left. His instructions were a bit vague but I had a general sense of what was expected. I looked over the clothes and that left little room for doubt in my mind. He had laid out a snow-white corset, matching thong panties, lacy garter, and nylons.

Now that I was alone (not even the dogs had stayed) I felt more comfortable. I took a bath cleaning everything that might conceivably need cleaning. I shaved everywhere a woman would shave and then a few more places for good measure.

When I was done I put on the sexy lingerie finding that it fit me perfectly. As soon as I was dressed his voice boomed over the intercom. He told me to go to the makeup table where I would find a wig and the other things I would need. It took me awhile to get it right and in the end I looked exactly like a sissy man in

woman's underclothes.

Steve came back in making tsk tsk sounds. He re-did my makeup until after an eternity he stood me up to look at his handiwork. He produced a digital camera and took photos of me in various poses.

Nothing I did was good enough for him and I was always being corrected. After what seemed like a great many pictures, he took the camera into the other room and came back without it shortly thereafter. Any thought I had of retrieving those pictures left with him.

After nearly an hour without words Steve spoke. "You are my slave and I am your master. Anytime I ask you to do something you will respond one of two ways. If it is something that you would like to do you will answer with "Yes, Sir." If I it is something that you would not like to do you will answer with "Anything for you Sir. Either way you will obey. Do you understand?"

I fell into the role just a little too easily to feel comfortable with myself and I answered "Anything for you, Sir." Indicating that I would do what he ordered me to do whether I wanted to or not.

He pushed me back causing me to fall onto the bed. Once on the bed he dragged my body into the position he wanted me in. He laid me on my back with my arms stretched out above my head and my legs spread eagle. I expected him to tie me up but in retrospect slavery requires more subjugations of the mind than of the body.

Steve turned down the lights, lit candles and played romantic music. Certainly not what I expected. He lay down next to me running his hands over my girly-attired form. He kissed me tenderly in all the places I kiss my wife when I make love to her: my neck, my cleavage, tummy, etc.

He was setting the tone. Making sure that I understood I was the girl and he was the man. He turned me over and repeated the process on my backside. I have to admit I was feeling adored and very feminine.

It was just about at this point when his attitude changed again. "Do me now, Bitch." He dumped me off the bed and took my place.

The mind games were crazy. I kissed him all over as he had kissed me. It was difficult being so intimate with a guy and it helped me to imagine I was with my wife.

He said, "Now on the lips." I didn't think he would want that. I didn't think I could do it. I wanted to run, screaming, knowing I would forfeit the good sex still to come. Mostly I just wanted to say no. I avoided the issued and kept kissing his fingers.

He said it again, "The lips," and added "slave." What could I do? I opened my mouth. I was either going to refuse, or kiss him on the lips. I said, "Anything for you Sir." I bent over his reclining body moving closer and closer to his lips.

Then came the instant when my lips touched his. His were hard and rough. Unyielding. He held me close kissing me back. His tongue was in my mouth. I don't even drink from another guy's glass and here I was with a man's spit covered tongue dancing around in my mouth.

He rolled over on top of me kissing more ardently. I was repulsed. After all I had been through I still hated the idea of kissing another man. But it didn't matter what I liked. Steve wanted this and he got it no matter what I wanted. I suspect he knew I did not enjoy the kissing.

I felt his hardness pressing against my leg. Meanwhile I was as soft as a wet noodle. This wasn't doing anything for me. As I have said all along, "I'm not gay." I even wonder if there is such a thing as gayness as opposed to the varied intricacies of the minds of millions of persons.

But was I a sissy? I did feel good in these clothes.

He kissed down my body swirling his tongue in my, now feminine looking, belly button. I felt nothing. Steve peeled off my nylons allowing his tongue and lips access to my legs and thong covered privates. He traced his fingers under my white lacy

panties, tickling my balls and delving into my ass crack. I could now read the signs and figured another fucking would be in my near future. I didn't know how I felt about that. It was great last time. But maybe this time wouldn't be the same. If Steve had a beer can thick dick it would hurt too much.

He slipped his tongue beneath the edge of my panties. Now this was starting to get good. My wiener hardened all stuck down between my legs.

My master said, "It's time to get a look at your little clitty girl. He fished into my thong with his index finger and pulled my "clitty" out into the open. Slathering my now bald nuts with saliva I was feeling real good.

I wanted to writhe around and maneuver myself into a better position for sex but intuitively I knew that a good sub allows her master to call the shots. He continued what he called "cunnilingus" and licked my clit for a time too.

Turning around he was now kneeling over me in a sixty-nine. I don't know when he lost his shorts but there was now nothing between my lips and his four-inch dick.

What the fuck? I thought he would have a big cock but it was small. Could a small dick make me feel dominated?

He continued to slather my balls and lowered his hips until he could rub the underside of his cock over my lips. He pressed down with a considerable amount of pressure, I pushed out a dollop of spit providing the slickness necessary for his dick to feel good rubbing over my lips, which were, for the second time in my life, painted with red lipstick.

His dick smelled subtly of man and it smelled great. He ground his pelvis into my head rubbing his wet cock all over my face. He took a special delight wiping his pre cum into my eyes smearing my mascara.

I didn't mind, I was now taken over by crazed lust. His cock entered my mouth and he fucked my head for several minutes.

Then turning me back over again I found my panties being sensuously rolled down to expose my rosebud. Lubricant was applied generously to my backside with a very inquisitive and intrusive fuck finger.

He raised himself up while I readied myself for the anal assault. Instead he got off the bed only to return a second later. Lying on his stomach between my legs he pressed something cold and wet to my ass. I thought it was his tongue but it turned out to be a small dildo. Pressing and twisting into me the dildo reamed my cunt and loosened me up. He raised himself up again, pulling the little plastic cock out.

I waited, holding my breath. Another dildo pressed into me. This one larger and textured. Steve continued this progression several more times, each time returning with an even larger plastic phallus. The last one was one of those double-ended life-like silicone cocks frats use as an initiation prank because no one would possibly use

something so impossibly big. He twisted and jammed it into my burning ass far up into my belly, farther than I thought possible. Grabbing it with both hands he pulled, but my ass didn't give it up that easily. He wrenched and tugged at it until it was finally removed.

Raising up he said, "I was going to fuck you silly but that ass is so loose it would swallow me up whole and I wouldn't feel the sides now. You worthless cunt."

He was blaming me for his small dick. What could he do to me now? I was dressed like a bride on her honeymoon night, kissed, headfucked, and sodomized with a rubber horse cock. Was the costume a waste? Would I go home with the shame of not being able to satisfy him?

Steve placed a collar and lead on my neck and yanked dragging me into another bedroom. I was taken from the bridal suite to the dungeon; from the frying pan to the fire. He threw me down on some pillows and proceeded to make some modifications to some odd table contraption.

I squeezed my butt muscles trying to get my sore ass to return to its previous state.

When he was ready he said, "Are you ready to hand over your life?" I didn't think he meant that literally, but it filled me with dread nevertheless. "Anything for you Sir."

He pointed to the table and I climbed up gingerly so as not to aggravate my asshole. The padded table contained a variety of holes and straps and looked slightly like one of those massage tables with a hole for a face to fit into. I was tied down tightly before a second table was lowered on top of me. The holes in this one were also strategically placed to allow access to any part of me one might want access to. "The party will start soon." He said as he left.

About a half hour later my confused penis had hardened and softened several times when master Steve returned with four naked friends. They were all well built like the weightlifters in the adult video store and they were all handsome, each with a monster cock.

He ordered them around like he ordered me around. I guessed that they were slaves too. Master said, "Go on boys, have a party."

They tilted me up so I was upright sandwiched between the two padded tables. The black haired man stood behind me rubbing my ass before he kneeled and tongued my cunt hole. He pulled my thong which Steve had put back on me to the side then ripped it off so he could get his tongue in without anything in the way. I had never been tongue fucked before and the feeling was indescribably good.

The tallest of the blonds knelt in front of me and swallowed my cock all at once. The shorter blonde licked my feet and sucked my toes. I could hardly stand it, I'm very ticklish.

The last, the only one whose name I heard, Mike, contented himself to rub his chest with my hand. I felt his nipples harden. I noticed that his chest was hard as a rock.

Steve sat in a chair fingering his dick. Somewhere I heard a clock chime. I had been here for two hours. Steve piped up, "Turn it around boys." Mr. Asslicker stood up and pounded his cock into my only recently normalized ass. Mr. Cocksucker turned himself around and impaled himself on my cock.

He beat his meat vigorously as he fucked himself on my pole. I would have gladly helped if I could have moved a muscle but I was bound as tight as could be. Asslicker/buttpounder came in my cunt. I felt every spurt shoot up into my insides, then, when he withdrew, I felt it all run down my leg.

The meatbeater shot a few loads on the carpet. When he came I felt every contraction through his ass. The feeling was awesome and I would have come myself if the restraints hadn't limited my ability to thrust my hips and somehow lessened my ability to come as well. Incredulously, Meatbeater licked up his come from the carpet.

I was then let out of my table/cage. Mike and the other guy went over to an oversized bed and lay down next to each other, as if on cue.

Steve spoke up again from his chair where he was still playing with his little dick. "Go make love to them." Indicating the two hunks on the bed.

I sauntered over in my best feminine walk, to where they lay, my curly wig bouncing airily on my shoulders. The guys looked at me and they liked what they saw. I felt pretty and desired. I climbed on the bed between the legs of the two handsome and very naked guys. I grasped one cock in each of my hands and stroked.

Steve spoke up again, "Make love to them, don't just sex them up." I laid myself down on their bodies resting my head on the flat stomach of the guy on my right. His cock was reddish, and inches from my mouth.

Ignoring this beautiful cock. I caressed their bodies with my hands, running my hands all over, feeling and appreciating every square inch. I squeezed their muscle-puffed chests, I massaged their broad shoulders, I patted their rippled tummies, I stroked their muscular thighs and I reached under to feel their perfect tushies. I then repeated my actions with kisses.

After pleasuring their bodies with my hands and my lips I moved up 'til my face was near theirs. Slowly I lowered my lips to Mike's lips. When our lips made contact I was looking into his eyes and he was looking into mine. I did it. I kissed a man full on the lips - and it wasn't bad. I french kissed him and he me. I could smell his minty breath. It was a passionate kiss full of intimacy and lust.

It could have lasted longer but Steve was playing his little mind games and he gave the commands. He was the boss, but he lost the game. While I was repulsed when I kissed Steve, these handsome studs got my best. We were both aware of his loss and I sensed he was fuming inside.

He stopped our kisses with three words, "Fuck the Bitch!" My strong manly lovers flipped me over. One got between my legs and lifted my ankles up onto

his shoulders while Mike stayed back.

Lining his shaft up to my asshole. I braced for the impact as he drove himself home. His fuckpole sank into my pussy and it was bliss. Like before, his cockhead hit all the right spots. With each thrust pre-cum was ejected from my cock, dripping all over the bottom of my corset. He established a rhythm and kept it going. I doubted he would ever stop.

Meanwhile, studdly Mike, threw one heavy leg over my chest sitting astride my false breasts. His long prick reached all the way from where he was sitting to my mouth. He pushed the head down smearing my lipstick all over its underside and simultaneously manly wetness on my lips.