I had been without a sub for a while until I met Bob. I'm 5' 8" and about 210 lbs with a thick 6 1/2" cock. My ideal sub is handsome and taller than I and trim. There is something very exciting about having a taller and trimmer guy for your sub. Bob and I messaged each other on line for a while before I decided he would be an excellent candidate. We arranged to meet first at a coffee shop. When he arrived I estimated that he was tall 6', trim and handsome with graying hair. As we had talked on line for a while, I already knew he was a sub, but I did not know how submissive and as he had posted no picture, I was not sure what he would look like: so I was pleasantly surprised. After we had talked a bit over coffee, I asked him to come out to the car with me because I wanted to test his degree of submissiveness. When we got in the car, I suggested going for a ride and as we drove, I reached over and felt for his cock. He looked shocked, but offered no resistance. I loved his immediate submissiveness as I fondled his cock; it seemed small. I was so excited by his degree of submissiveness that I drove to a more private place where I unzipped and showed him my erect cock. Bob stared at it, but froze: so, I reached over and place his hand on my erection. I asked him what he thought and he said "Ohh," he murmured, " it's so big and thick". I asked him to unzip and show me his cock which he obediently did. It was even smaller than I realized, maybe about 3", but a perfect size for a sub. I thought, oh yes, you are going to do fine as my new sub! I asked him if he would like to meet at a hotel. He said he would and we arranged to go to a motel the next week.
When we arrived at the motel, I went over and sat on the bed. I like to do that because it puts my subs in submissive position. I watched to see what Bob would do. He was obviously anxious, but he quickly took off all his clothes and stood submissively naked before me. I continued sitting on the bed and as I slowly examined him I said "Very nice!"as he stood there naked. To build his submissiveness, I took my time looking him over and after I saw the he was trembling. I softly said: "Turn around Bob; I want to see your ass." By staying fully clothed and ordering Bob to display his ass for me, it immediately put Bob in a servile position. I was pleased to see him obediently turned around. While his back was to me, I reached over and gently ran my hand down his back and cupped his cute little ass. This way I established firmly in his mind that I was in charge of him sexually.. I also could see it excited him as he was trembling in anticipation. He was well proportioned with a flat stomach, nice chest and prominent nipples, a soft ass and small cock. I sat and stripped off my shirt and shoes and socks abut left my pants off as I wanted to see what Bob would do. I stood up and moved in front of Bob. He immediately knelt like a good sub and and reached up with trembling hands and asked me if he could unzip my pants and take out my cock. It always thrilled me to see a sub asking to pleasure me. I could see his hand shake as he unzipped my fly and reached in to gently pull out my cock. Drops of precum were already leaking from my pee slit. He stared at the precum spreading over my throbbing cock which was pulsing in his hand. He whispered: "May I kiss him?" He was clearly eager to blow me. "Ph my, Yes, you may, Bob" I love looking down at subs when they are bending forward for the first time to take my cock into their mouths. Their servile position seems to excite them. I was definitely excited that Bob immediately knew his place at my feet. I felt his lips kissing my cockhead and felt his tongue licking my precum into his mouth and then watched as his mouth enveloped my shaft with his lips firmly wrapped around my cock.. His mouth felt so hot as he sucked more of my cock into his hot mouth. It excited me so much, I wanted to fuck him right then but I knew from our previous conversations on line that he was reluctant to engage in penetration. Although Bob was inexperienced, he was giving me me an excellent blow job but when I withdrew my cock from his mouth and and sat and raised my legs to offer him my ass to rim, he was hesitant. I knew not to push him any further. I took his face in my hands and brought his mouth back to my cock. He seemed relived to return his hot mouth and lips to my cock. As I looked down at him kneeling with his soft lips wrapped around my cock, I knew I would be able to break down his resistance to rimming with the proper preparation. I was confident I would be able to take his ass too. I love the challenge of taking a sub step by step from bisexuality to accepting being a submissive bottom. Bob had no idea how quickly I would turn him. It took patience and praise, and a commanding attitude. These subs are born to serve! There is something even more exciting about topping at tall handsome straight looking guy with a virgin ass who did not think he would allow himself to be fucked and introducing him to the pleasures of offering his ass to dominant man. I was excited about the prospect of seeing the look on his face when he finally realized I was going to fuck his virgin ass. I was so excited at my thoughts, I had a powerful orgasm. Bob tried to swallow all of my cum, but a little oozed out of the corners of his mouth. I was thrilled to see him use his tongue to try to lick the cum back into his mouth. That evening Bob messaged me that when he arrived home, he could still still feel the taste of my cock in his mouth and the impression it had made on his tongue and he had an intense orgasm.
The next step in Bob's submission on came when a couple of meetings later when before we showered I asked Bob to kneel beside me and hold my cock while I was taking a piss. It sometimes takes a few times before a sub accept that this is one of his duties. But Bob did not hesitate. After I finished, instead of asking him to shake off the piss drops, I decided to have him was he the piss with his mouth; so I turned towards him and offered my cock so he could clean it with his mouth. Bob did not hesitate. He leaned forward and stuck out his tongue and cleaned all the piss drops off my cock and then sucked my cockshaft into his mouth to wash it completely with his mouth. When I asked him how it tasted, he said: "I was so aroused when you offered me your cock, I just wanted to obey and that excited me."
Bob still had not taken the next step in his submission to rim my ass, though I kept brining up how much I enjoyed it. Finally one day while we were showering, I bent over to offer him my ass and spread my ass cheek to allow him access. To my surprise, Bob finally gave in and leaned forward and placed his soft hand on my hips and I felt him gently plant wet kisses on my hole, followed by little tongue licks. Unlike my other subs, his kisses were gentle and almost feminine. After that he actually started rimming me on a regular basis.
It excited me how submissive Bob was becoming. I talked to him about how I liked my subs to be smooth, shaving their pubic hair off. He not only shaved his pubic hair, but started shaving under his arms and chest and legs. After a few more oral session, I discovered Bob loved dressing up. I encouraged him to do more and he addd make up and lipstick. So, I decided to feminizing his name by calling him Bobbie: it was meant to make him aware that he was no longer a man in our relationship but a sissy and I wanted to get him use to the idea that I thought he was a sissy and not a real man. It seemed to excite him even more. From my experience with other subs, I knew that once they started to submit to my increased demands, they eventually realize that their submissiveness extended from their mouths to their asses. But all in good time. I was excited at the prospect of Bob understanding that I was not going to be satisfied with his blow jobs, I wanted his ass too. I wanted him to lead him to the point of submission where he understood that his primary sex organ was his ass. When subs arrive at that point, it's important to keep them on edge by not allowing them to pleasuring themselves until after they have been fucked... When Bob arrived at that realization, he have to understand not to touch his cock until after I had finished fucking him. It excited me think about the day when it dawn on Bob that his pleasure would now come primarily through his ass. I wanted him to reach the point where he would accept my telling him his ass was really a pussy to me. There is nothing like the excitement of seeing my cock penetrating the virgin ass of tall confident handsome formerly straight man.
I planned my next move and started bringing up the the subject of anal penetration with Bob more often. Bob believed that he was just playing a sexual role when he dressed and put on make up, but with the right touch he would come to understand he was a real sissy, not just playing a role. Bobbie was definitely a real sissy . By calling his ass a pussy, I was introducing him to the idea that his ass was meant to be fucked. I talked about how I fucked all my previous subs and how much they all, even the virgins, eventually came to enjoyed it. But I did not directly pressure him as I knew my discussions about my experience fucking my other subs would start to excite him. I also told him how I often looked at anal porn an how much I got excited by it; I was confident that would peak his interest in seeking out anal porn on his own and I was sure when he did it would make him more excited and curious. These bottoms, and Bob was a bottom, are all alike; They all love servicing cocks. Their submission was a one way street for me. Cocksucking would lead to ass fucking . What Bob did not realize was what a small step is was going to be for him to go from servicing cocks with his mouth to servicing them with his ass. Once he start watching sissy bottoms getting fucked, he would start identifying with bottoms and the excitement he experienced would begin to make him focus on offering his ass to be fucked. I like to let my subs discover how submissive they are on their own with me giving the merest of suggestions and so I continued to give him the slightest praise like "Bobbie you are the most talent cocksucker I've ever had. You are such a natural at it. Oh Bobbie, you are a pretty sissyboy. Look at how hard your tits get when you are excited!" I would caress his ass and thighs and breasts just like a girl, telling him: " Bobbie. Your ass is as soft as a girl's ass. Even your tits have a feminine quality. Nipples get so hard when you are excited. I love looking down at you face and see your lips wrapped around my cock." In his excitement, Bob would would look up at me with such lust his eyes. I loved looking at his nude body and soft ass and small cock that I referred to as his cockette and imaging how much pleasure I was going to feel as I fucked his hot little ass.
In our next session when I arrived, he was dressed and looking very sexy. I kissed him fill on his lips with my mouth open and tongue probing. As I kissed him, I ran my hands down his back and cupped his cheeks pulling him closer so he could feel my cock pressing against his cockette. My need to fuck him was growing. I Brought up the subject of anal penetrations more forcefully. As we lay together after he had blown me, I started caressing his ass and using my finger to penetrate his hot hole and and as expected he showed no real resistance. I then asked him lie on his stomach with his legs spread allowing me better access to his ass. I got him use to me caressing his ass and teasing his ass crack. The next step was using lube when I fingered him. I told Bob to lie on his stomach so I could take her to the next stage of her discovering pleasures of anal sex and further identify with his emerging gay bottom desires. The next step involved lying on top of him and spreading his legs to the point where I could slide my cock up and down his ass crack and to tickle the opening with the tip of my cock. "Doesn't the feel good, Bobbie?"At first he resisted. "I afraid you're too big for my ass," but he was clearly excited. I told him not to worry wouldn't go in unless he wanted me to do it. But I continued testing his ass opening to see how tight it was. I could tell Bob's ass was tight. I began discussing with Bob how my subs prepared their asses for fucking. I pointed to some web sites he could look at. At the next session I could tell he had lubed his ass before coming as it was wet to the touch. Bob was ready, but I resisted taking his ass right then, though I was so tempted, because I wanted to build his desire to be fucked. Once I fucked him, the pleasure of having a hard cock in his ass would make him realize he was a true bottom, and that true bottoms need to submit their asses to their doms and that they get intense sexual pleasure from being fucked.
After a few more sessions, Finally I decided Bob was ready. To get him completely aroused I had decided to have him suck my cock and get him to deep throat it for the first time. I was torn because I wanted to save up a good load for Bob's ass, but I knew I could recover and still have a load for his ass. I continued to praise Bob's oral skill. I told him to focus only on my cock. "Kiss my cock with your sissy lips. Make him wet with your sissy tongue and then kiss the tip for me." Bob planted a soft gentle wet kiss on my mushoom cockhead. I drew back slightly and I could see a thread of precum bridged from my pee slit to Bob's lips. I wanted to test him and withdrew my cock a.little more breaking the thread. It always thrilled me to see how eager sissies were to continue sucking. I knew how to get the best out of sissies and Bob was no exception. I watched as Bob's tongue exited his mouth to reach forward to my pee slit to draw in more precum into his mouth. By now in our sessions, it was like nectar to him He leaned forward and ran his tongue under the ridge of my cockhead. I could hear his slight moan, "mnnnnn" he hummed. Bob bent his head forward to reach my cockhead with his mouth, lashed frantically at it with his tongue and and lips trying to get more of my sweet nectar. I paused to lavish praise on Bob's skills, stroking his hair. "Bobbie, You are the best little sissyboy ever!." Such praise made Bob feel he was doing a good job and the more I complimented him on his cock sucking skills, the more he endeavored to swallow.. I loved looking down at him while he slavishly serviced my cock. It was so erotic watching a sissy become a cock slave, but I want to increase his need for my cock so I withdrew it from his mouth again and told him form an oval with his mouth and when he obeyed, I brought two fingers and laid them on his tongue. "Suck, sissy. Suck on my fingers with your loving tongue, Bobbie!" Bob had a look of desperation in his eyes, he needed the sweet nectar but he needed to submit more and he sucked hungrily on my fingers as though they were little cocks. . I stepped forward and took my cock in my hand my and began to tap on his tongue with my big wet cock. The I slowly thrust my cock in his mouth until it hit the back of his sissy throat. I could feel Bob gag a little but his tongue started moving back and forth on my shaft. "Bobbie, Don't move. Just let this happen. Keep your mouth wide open and your tongue stuck out. Take a nice deep breath, think to relax your throat. Once you do, your gag reflex will let your throat muscles grab at my cock and milk it. I love that so so much. Bobbie, Accept my cock as a gift my little sissy! " I placed one hand behind my cocksucker's head and ran my other through his hair. Ahh he will soon be ready for what I want of him. A few more words of praise, eye contact and gently whispered words of encouragement , I would get what I wanted.I began moving my cock in and out of Bob's mouth. Sometime I could see him looking up at me, his face awash with lust and desire.. His lips and cheeks and chin now started getting covered with saliva and precum. As I with drew from Bob's mouth I could see the shaft of my cock was now covered and dripping with Bob's saliva. On my next thrust, five inches were buried in Bob's mouth and bumping at his throat. He gagged again but his gags were becoming softer. I knew my repeated thrusts were starting to numb his gag reflex. He gaged a bit on each thrust. I withdrew it and could see it was completely coated with Bob's saliva. I thrust it in again and I could see saliva spilling out of the corners of Bob's mouth. His mouth was stretched as wide as it could go. I wanted him to get use to having his mouth filled and to enjoy the taste of my cock, so the when I withdrew he would feel a sense of loss and yearn or more. I knew I had to pull back and allow Bob to catch his breath, but as my own pleasure increased, those gaps between the withdrawal of my cock from this cocksucking mouth and subsequent re-entry became shorter and shorter. I was now in control fucking his hot mouth. As Bob gagged, the way cocksuckers do, more and more spit came out of his mouth and more thick threads of precum and saliva were soon spreading all over his face and chin. The wetter Bobby's cocksucking mouth became, the harder my cock got. I wanted Bob to take my entire six and a half inches and feel my balls on his chin as my cock entered his throat. "Ohh that feels so good. Bobbie. Let me feed you more cock. You love taking more of my cock, don't you?'" I hire another moan "Mnnnn." "Is that a yes, my sissy? Just look up at me and good your head or blink your eyelashes like a good sissy" Bob looked up and batted his eyelashes. Ohhh I moaned "Such a good sissy Bobbie!" My smiles and words of encouragement, the gentle massaging of his head and hair and cheeks seemed to increase his need to suck more sweet nectar from my cock . I knew my cock was now slippery enough to make it easier to slide it into this poor sissy's throat. "Bobbie, That's a good sissy. Good sissies need cocks so so much. Just relax you throat and let my cock enter just like a perfect sissy. You want to be a perfect sissy, don't you, Bobbie?" He responded "Mnnn" as me cock was now his only focus. My need to cum was exciting me so much. "Now open your throat and take my cock deeper. I was spurred on to force it through and down his throatI Now all six and a half inches were fully inserted in Bob's mouth and throat. "Arggghh" he gasped. "Breathe through your nose, Bobbie!" His lips were now pressed agains my groin. I with drew into his mouth and shoved in again. "Arggg " he moan again, but I could see his resistance was gone. "Oh Bobbie, I can feel your throat massaging my cockhead. Oh you're such a good cocksucking sissy! Now make me cum like a real gay cocksucker ". I had never used the term gay before but I wanted him to realize he was my cock slave. I with drew into Bob's mouth and started cuming in little spurts then more and more. I could feel poor Bob trying to swallow but there was too much cum and it oozed out of the corner of his hot greedy mouth and ran down his chin. I was so exillerating to see cum dripping from his lips and running down his chin.
I was spent but we were going to have all day and Bob was so sated with cock and cum I knew he now needed to cum himself. But I needed to deny him the pleasure of coming until I fucked him. I wanted to treat him like a bottom and the best way for a real gay bottom to cum was to have the cum fucked out of him . I was so pleased with myself that I was going to take his gay sissyboy ass.. I told him "Bobbie, I have a special treat for him. It will be even more exciting for you to delay your orgasm until after I give it to you." I was determined to prevent him from cuming until after I had given him the treat. So I withdrew and sat across the room. I watched as he writhed on the bed in frustration, licking the cum off his lips using his finger to scrape he cum off his chin He was nude and and when he turned over, I could see by the dim light of the TV that he was spread eagle. In the dim light I could see Bobbie had spread his ass wide open before me. I stared recovering and I knew in a minute that i needed to be in him, bareback. I was already rock hard again as i approached hIm and ran my hands up and down his body, over his hips and ass, caressing him, running my hands down over his ass and down between his legs and exciting him with my caresses: "ohh Bobbie, so smooth like a real sissy," Oh fuck! I want to fuck him so badly ! and caressed his soft ass and spread his ass cheeks and thighs to allow me better access to his hot little pussy hole and told him "Bobbie, my sweet little sissy, I'm ready to give your present." I was going to fill his sissy ass with my cock. I had enough left so I was sure my cum would drip out of his ass when I finished. .At this stage, I knew Bobbie was both terrified of having my huge cock in his ass and yet hungry for it He was now on his stomach and pressing his cockette in the bed trying to cum. To further his humiliation I stood beside him and as he turned his head, I presented my cock to his mouth and told him: "Bobbie, it's time to lube it up my cock with your own saliva. Make him nice and wet and slippery." I had not yet told him what my present was going to be. , but his sucking and excitement told me he knew. I wanted him to understand he was going to participate in his own fucking and it definitely excited him as he eagerly started bobbing up and down my shaft bathing my cock with his saliva, the best lube for a sissy. . When I saw that my cock was glistening with Bobbie's saliva, I turned him over on his back and bent over and to kiss him thrusting my tongue deep in his mouth and ran my hand down over his cockette and and tiny balls and under to his ass teasing his hole. I with withdrew my hand and reached for a small tube of lubricant, Bob had no idea what to expect. From his reaction I knew was that he had been responding to my probing. My second hand followed the path of the down his ass to join the hand already there. It must have surprised Bobbie a little to feel the wetness on the new finger that replaced the one that had been there. I continued to probe his behind but it was different, after a few testing touches, I slipped it in!
Bobbie gasped as it entered him. "Oh! Oh! Oh yes!" he said breathlessly. I leaned in and whispered in his ear: "Bobbie, I'm so glad you like this honey, I have to show you more, I must show you how good a sissy can feel. You'll know you're real sissy, Bobbie, when you have taken my hard cock up you pussyass.I know you are ready"
Bobbie "Yes, oh yes, I need your touch so much."
I went from testing Bob's virgin hole to leaving my finger in it. I slid in only from the tip to a knuckle. I could feel Bob tighten his ass out of instinct and then relax it. I was so pleased that I was finger fucking Bob and that he enjoyed it. It was a good sign that I was going to get my way. I then reached around with my other hand and found Bobbie's nipple, which was hard from his arousal, pinching and twisting it as I fingered his sissy hole.
I recognized Bobbie was now helpless to the passion he was feeling. His cockette was soft but leaking precum. I was bringing him to new levels of passion and he loved it. With each push of my finger, Bobbie was getting more and more used to this new sensation and he wanted more with each stroke. His hotlittle ass moving with each stroke of my finger. I now inserted another well lubricated finger I felt his ass relax to the point where more than 2 fingers would fit, I knew Bobbie was ready to be taken. I lubed up my hard thick cock and dribbled more lube on his hot writhing hole. I turned him over onto his stomach as I wanted to mount him from behind first. Bob raised his ass offering it to me just like a hot gay bottom. Before I took his ass, I looked down at his virgin ass writhing up and down in anticipation.I pushed forward watched as the tip of my cock slipped forward and just like that popped inside. I felt the hot tight ass of my sissy. As I stood above him I grabbed his soft hips and drove my cock in deep and hard. "Yes my gay bottom, feel my cock in you, I feel your ass tightening on my cock, Bobbie, just relax, relax and take more, take more of my cock into you."The thrill of taking his hot little ass was intense. His hot little ass fit my cock like glove. I whispered to him "Push against my cock, Bobbie. Breathe deeply and relax.". I watched my hard cock disappearing into this sissy"s ass and the sight made my cock even harder. Bob cried out."Ohh it hurts!" but did not push me away and soon began to moan and push back. Bob's virgin ass was so hot and tight and I hadn't fucked a man in some time that I doubted was going to last long.I made it in all the way balls deep into Bob's ass. I pumped him for a few minutes then withdrew and turned him to face me and took him missionary style. As I started to fuck him again, Bob began making moaning and grunting noises. In my excitement I increased my pace, my balls slapping his ass as I pumped deep into him. I raised up so I could see Bob's cockette , saw that it was soft but leaking copious precum. A soft cock of a sissy being fucked is a sure sign that he is a real bottom. His ass started opening up nicely on the inward stroke, and he moan in ecstasy, and on the outward stroke, his tight ass, his man pussy as it were, almost seemed to cling on to my cock more tightly, reluctant to let it leave. I held him by the hips and pushed in until he bottomed out, Bob was now whimpering with pleasure. Oh how my sissies, my bitches, scream out when I did this. I squeezed Bob's ass from both sides so his pussy would hold my cock tighter. I could feel Bob's sphincter relax and I began fucking in and out more forcefully as I could feel my lust began to dominate. On my next thrust Bob wrapped her legs forcing my cock deep in her ass. I looked down at my cock splitting her ass just the way a bottom''''''';''s ass should be split. There was extra excitement because now Bobbie this tall handsome man was surrendering his virgin ass to me. I whispered to her. "Bobbie. What a good sissy boy, you re accepting my cock. You have such a hot ass, hot asses need cocks, I just have to fuck it honey and I just have to be the first to have your sissy ass. Do you hear the sound of my balls slapping against your ass while Im fucking you. It's the sound all sissy bottoms get to love.". There is an inherent humiliation of being a submissive bottom being fucked by a real man. I could see in his eyes the confusion of having six and a half inches of a hard cock in his virgin ass and realizing the humiliation mixed with excitement. I was so close to cumming and then I felt Bobbie's sphincter spasm and tremble in orgasm and I looked down to see his cockette spurting rivulets of cum. "You're a full fledge gay bottom now, Bobbie. My cock is fucking the cum out of you now. Only faggots cum when they are being fucked."
"I had never called him a faggot before and I could see in his eyes widen with the recognition and humiliation that I thought he was just another gay sissy bottom faggot to be conquered and fucked. That look brought me over the edge and I came again pouring more cum into this sweet faggot's ass. I felt the cum leak past my still hard cock and run out of Bobbie's ass and down his legs. I had taken him down to another level of submission and incredibly he was even more excited and aroused. I was the complete master of his ass, now. He looked up at me in confusion and wonder as it dawned on him that he really was a faggot bottom, just like every bottom he had watched in porn. My other subs all could be taken as I wanted, but Bobbie thought he was not like them. In fact he was even more of a faggot. I wanted him to realize that and fully accept his humiliation. He was a sissy faggot who liked to dress and shave his body and wear lipstick and makeup and do his hair and pretend he was a girl. I knew this tase of humiliation would increase his desire for more humiliation and more cock. I knew once he had realized he was jo different from a common bottom, he would be coming back for more , My experience with these sissies was that once I had taken their asses, they begin to be thrilled by the idea they are faggots and they feel an increasing need to submit more and look for chances to be fucked again.