A Sissy Story

I got very excited writing the following story

I always considered myself straight. I was married and at 55 my kids had flown the coop. But over the last few years I began to fantasizing about cocks and being submissive to a more masculine man. I was 6' tall fairly trim at 175, but with a small 3.5inch cock. I never thought a lot about the size of my cock until one evening while I was traveling I visit an adult video arcade. When I entered one of the video booths, I saw a hole about waist high. I put some coins in and was watching a video about a girl who was giving blow jobs and I was getting so excited, I started stroking my cock. Just after I started a light went on in the booth next door. I was fascinated and bent over to look. There was a guy stroking a cock that must have been at least 8 inches. It was beautiful and as I stared at it. I got on my knees to get a better look. Suddenly the guy turned and walked towards the glory hole. I rocked back on my heels but he slid the cock through the hole. I was mezmerized and tcould not resist touching it. I ran my hand lightly done the shaft. It felt smooth and warm. I bent down and rubbed it on my cheek. I was so excited and thinking about kissing it but just then someone tried to get in my booth and I backed away, zipped up and rushed out of the booth flushed with embarrassment. When I returned to my room, I stripped and masturbated until I had the most shuddering orgasm I ever had had. After that I took to visiting more adult video arcades and watching cocks and fondling them, but I could not bring myself to sucking them except in my fantasies. After a while I started visiting bi chat rooms when I travelled or when my wife was out of town.

After two years we moved to another town because my wife took another job that required her to travel. Or next door neighbor was an obnoxious guy. He was in his early 70s about 6' 4" wiry and pushy. He tried to intimidate me over some disputes. My wife called him the old goat as she caught him looking at her from his window when she came out of the shower one night and he was always coming over to our backyard while she was sunbathing. I started going to the local gym to work out. He went to the same place and seemed to take great delight in taking the place next to me and doing many more reps than I could manage. He was really in terrific shape despite his age. One day he followed me into the showers. It was late and there was no one else there. He took the shower opposite me and I couldn't help noticing his very large cock as he started soaping it up. He almost seemed to flaunt it. I must have been staring at it because he broke the silence. "Pretty big, isn't it especially compared to yours." i was shocked but muttered "My wife never complained." He chuckled and replied "Thats because she has never had a real cock. I bet mine would really turn her on." I flushed and quickly turned off the shower and headed to my locker. But i was dimly aware that my little cock had gotten excited in hearing him talk to me that way. I hoped he did not notice my state as i walked past him. I was sitting on a bench still stunned at the exchange when he walked to the locker i was facing. As I was bending over to put on my socks he spoke again. "Here, take a closer look." I could not avoid looking up when I replied. His cock was huge. As i stared at it again my little cock began to get aroused again. Somehow my mouth started to make excess saliva. I flushed as I replied. "i'm not interested. You are mistaken." I turned and drew on my black silk men's briefs. He chuckled again and said "What a sexy ass. It could pass for a girly ass." He actually cupped one of my ass cheeks. I was completely mortified and embarrased and hurredly finished dressing and left the gym. "Any time you want to ask me over to fuck your wife, let me know." he said. "Right, like that is ever going to happen.". I replied. I was angy and I should have socked him, but he was too big for me to hadle despite his age. Also, I could not ignore my state of arousal. My little cock was still hard when I got in my car.

I had been visiting cross dressing sites for the past year completely in secret. That was the reason I had been wearing the silk briefs. At the crossdressing sites I had chatted to a number of other guys interested in crossdressing. Recently one of whom seemed to seek me out. I gradually started to reveal all my submissive fantasies to him. He was very sympathetic, but obviously much more assertive. After a while, he asked me to call him Daddy. He drew me out to talk about my sexual fantasies and urged me to dress up in my panties and fishnet stocking when i talked to him. Then he became more assertive calling me a sissy. With his guidance, I began to purchase more sexy fishnet stockings and panties, miniskirts and even lipstick. He was the one who suggested I start wearing men's silk briefs. He got met to admit my excitement about becoming a submissive sissy. He suggested I live out my fantasies, but I said I did not think I could ever take that step, but I told him how excited he made me and how I wished I could overcome my fears. Our sessions always left me so aroused I always went and stroked my cock and imagined what it be like to be dominated by him and worship his cock.

Then one night I was really horny. My wife was going to be out of town for two weeks. I dressed up in black sexy panties and drew on my sensuous black fishnet thigh high stockings and even put on lipstick and eyeliner and contacted him. I told him my wife was out of town for two weeks and I could dress up as sexily as he wanted. He said he was finally going to send nude pictures of himself naked from the waist down. When I got them, I thought to myself he looked somewhat like my neighbor. He was also wiry, obviously older with a very big cock with a huge mushroom head. But I thought no. It is just a coincidence. He asked to send him a picture of me as i was dressed now. I thought it would be sexy if I showed my body in silhouette before my bedroom window profile so he could not see my face. When I did, he replied telling me how sexy I looked and asked for another picture a long focus shot. I immediately sent him one. He then began asking me more about my wife and what our sex life was like. I told him how she really preferred my bringing her to orgasm with my mouth. I described her body and tits. He asked me about the color of her hair, her height and weight. I did not know where that was leading, but right after I finished describing her he shut down and I began to stroke my cock imagining myself on my knees sucking his cock.

A couple of minutes later I heard the doorbell and tried to ignore it, but whoever was ringing would not stop so I grabbed a robe and slippers to hide my outfit, washed the lipstick from my lips and hurried to answer the door. When I opened it, there was my neighbor standing there in his robe. "May I come in." he said. I was flushed with embarrassment. "no. I'm busy. " Look, I know what you are doing." He said. "You have fishnet stockings and panties under that robe. I am the guy you have been you have been chatting with.". With that he just barged in and shut the door. I was stunned and embarassed. I redened as I realized how I was face to face with a guy I had revealed all my desires to be submissive to a real man with a masterful cock. This couldn't be that man! He was an old goat. But he stood there towering over me. While I stood there, he just reached over and pulled my robe open. "I'm just pretending" I said "I'm really not a sissy. I've never been with a man." He replied "Look at yourself. All dressed up like a sissy. Look at your little cock. You know it is not even a cock. It looks more like a clit. Let's call it a cockette. Look at how aroused it is getting. all excited as you just stand there dressed up like a sissy slut in panties and fishnet stockings." I looked down and I could not hide my excitement. My little cock was tenting in my rose panties. "Please don't tell anyone" I said softly. He laughed. "Oh you are a sissy, all right. All those fantasies you shared with me. Playing with yourself while you looked at images of cocks. I bet you always went immediately to rub your little clitty when we finished our sessiond, Didn't you." I was so stunned I couldn't answer. "Answer me, you sissy slut. Didn't you." "Yes" I whispered. " I was sure you were a secret sissy after seeing you at the gym. I thought to myself you were a man who needed to service other guy's needs, serve their need to have their cocks serviced and sucked. You have the look of a sissy with that sexy ass and trim body and pouty lips just made for cocksucking. Then when you anonymously sought me out on the chat room, there were a few things you said that made me suspect it was you. Then today when you showed me those pictures of you in your panties, I saw in the background that unique bedroom window that had to be your house. Then when you described your wife, that clinched it. With that he walked around me and slipped the robe off my shoulder. I heard him drop his own robe. I stood there nervously as he stepped closer to me. I felt his body move against my back. Then he began to run his hand lightly down my back and cupped my ass. I trembled and shivered at his touch and my cock twitched at his carress. "What a lovely ass you have. Just like a little girl's. Look at how your little cock is getting arouse. Looks like your panties are getting all wet with precum just from my caressing you lyour ass. You love it, don't you." "Please" I said."You are making me so nervous." He moved right up against me so his chest fit snugly against my back. I felt his breath on my neck. I felt his cock moving between the split of my ass cheeks. He ran his hands around my waist and pulled my close. "Now, my little sissy, feel a real man's cock". I heard my own intake of breath. He was getting me so aroused. He reached around under my arms and caresses my stomach and ran his hands up accros my nipples which were now standing at attention. I heard a moan and then realized it was my own. "Oh yes Baby, I am going to enjoy taking your cherry" "Please don't. I don't know what to do. I'm not gay. I've never been with a guy". I whispered. He ran his hands down under my panties and caressed my cock. "Oh my. You do have a tiny cock. It really is a clit rather than a cock. My cock would be insulted to be compared with that little clit. It's a cockette because it is not big enough to be called a cock. It is getting so excited just being near a real cock. Bobbie, yes I think that's a good name for you. Now you are going to meet a real cock. You want that, Don't you?". The way he was talking to me and caressing my body had me so excited, I could only murmur "Ohh". With that, he put his hands on my shoulders, turned me around to face him and gently put pressure on my shoulders. I had no resistance and sank to my knees. There in front of me inches from my lips was his big thick manly cock. It was at least seven inches. It had a big mushroom head and I could see the veins as it pulsed and throbbed before me. I couldn't take my eyes off it. It was rising towards my lips. Its veins seemed to pulse suggestively drawing me towards it. I was mesmerized and excited. I knew he was an old goat, but I felt myself drawn towards that cock. I ran my tongue wetting my lips in anticipation. I could not resist wanting that cock in my mouth. "Look up at me Bobbie. You want to suck and service my cock, don't you, Bobbie? You have to earn it by begging me for it. You have to prove you are worthy of being allowed to suck my cock and be my cockslave. Now look at me. I want to see the look in your eyes when you taste my cock for the first time. Now oval your girly pouty lips like a nice sissy. Just wide enough so your mouth can handle a real cock. I just want your lips to lightly graze my cock. You are not permitted to suck it yet. I am going to run my cock into your mouth and lay it on your hot little tongue. Butbyou can't close your lips and begin sucking until I tell you." I pursed my lips into a wide pout like he told me. I wanted to continue looking at his cock but he took his left hand and held my chin so I had to look at him. With his right hand he held his cock and started inching it into my mouth. I was trembling with excitement as I felt the skin of his cock entering my mouth which was now wet with saliva and hot with anticipation. "You can't start sucking it yet, Bobbie. Just let it lie on your tongue and get use to the texture and feel of a real man's cock. Take a deep breath and smell it. You are making my so hot. You can smell my musky sex odor, can't you Bobbie. yes, you want my cock. I can see it in your eyes. You want to wrap your lips firmly around my hot shaft and milk it for all my hot cum. Don't you my little sissy? Say please Daddy and I will feed begin feeding it to you". I actually tried to say please with his cock in my mouth I was so excited kneeling there with this real man's cock in my mouth resting on my tongue. I was so incredibly excited the was he was calling me a sissy. "Ohh Bobbie, you are such a sissy. You just want to please a real man, don't you. Now, start sucking. When I plant my seed in your tummy you will be coming back for more. I'm going to breed you into a real sissy cocksucker.". By now I was so aroused I greedily started sucking and slurping his cock . Greedily I sucked as much as I could into my mouth until his cocked hit the back of my throat. There were still two inches I could not take. I was bobbing up and down on his wonderful cock not caring I was on my knees servicing this old goat. Then I felt him put his hands on the back of my head and with my down strokes and he started increasing the pressure until he finally pushed the head of his cock into my throat so that I began to gag. "Oh yes my little sissy, you are going to have to take the whole cock so I can pour my seed right into your tummy.". He grunted and pushed again and again. I was helpless. He was using my mouth for his pleasure but that was making more excited. My little cock was throbbing with excitement. I could feel my panties getting all wet with precum. Then finally he forced his cockhead past my gag reflex. I felt him shudder and cum shot down my throat into my tummy. He pulled back and his cum filed my mouth. So much that it dribbled down my chin and onto my panties.

As his cock started shrinking, I reached down to take my cockette and pleasure myself, but he grabbed my hand." Oh no. You only get to service me tonight Bobbie. Let's go upstairs to the bedroom. I want to see you in lipstick, eye liner, false eyelashes and blush just like you told me when we were chatting. And a bra and mini skirt to show off your sexy ass. I loved the way your full lips looked wrapped around my cock. You are such a naturally talented cocksucker. You really knew how to service a cock. Your the first guy or girl who was able to deep throat my cock the first time.". With that he took my hand and led me up the stairs. I was still in a daze of lust. My little cockette was aching for relief. He led me to the dressing table in my room and started applying blush and lipstick. Then he looked at the bra and mini skirt I had hidden and ordered me to dress in them. I slipped them on and felt a thrill dressing for him. "Now you look like the horny slut you have told me about. Oh yes, You are going to really feel like a girl tonight. I bet you cant wait to get more of my cock, can you" I could not believe that I replied "Oh please tell me how I can please and excite you, Daddy. He then went over turned on some music and came to me and put one arm around my waist and pulled me close. He was still naked and I could feel him getting aroused as we danced. He reached up and pulled my neck down and kissed me. He opened his mouth and ran his tongue into mine and I sucked greedily on his thrusting tongue. His hands started caressing my lower back and then they slipped under the waist band and panties and caressed my girly ass cheeks. I was getting so aroused again that I was ready to do anything he asked. As we danced closer to a table he picked up a tube and when I next felt his hand on my ass again it was wet with lubricant. he ran his hand between my ass cheeks and started fingering my pussy . With lubricant it slipped easily in. "Spread your ass cheeks for your Daddy." he ordered and I immediately obeyed. He pulled me closer and I felt his cock press against my leg. At the same time he slipped two fingers into my pussy then three as i squirmed against him and stared humping his leg to rub my clitty on his leg. He pulled apart and led me to the bed and said: "lie down on bed, Bobbie." i went to lie on my back but he turned me so I was on my stomach. He parted my thighs and knelt on the bed over me and began caressing my my ass and thighs. Then he pulled my paties roughly until they ripped off my body exposing my naked ass. I moaned and tried to rise. "Please, I can't do this. I'm scared of the pain. Please don't do this to me Daddy." He shoved me back down on the bed with one hand and with the other slapped my ass again and again so hard it stung and brought tears to my eyes. "Bobbie, I'm going to fuck your pussy and there is nothing you can do to stop me. So you better relax and not struggle. It might hurt, but after a while you are going to get so excited, your little clit will start throbbing and you will be begging me to fuck your pussy. Tomorrow when you remember my cock inside your cunt, you will be calling me to come and fuck you again. You are a sissy and that is what sissies want." He then paddled my ass until tears began to run down my cheeks. When he saw my tears, he switched to carressing my ass and gently spread my thighs further apart. His hand began circling down to carress and tease the opening to my pussy, dipping his wet fingers around the entry to my pussy and then inserting one finger and then two fingers. He wet his fingers with more lubricant and began the process all over again until I began moaning with pleasure and began pushing back against his probing fingers. The he really picked up the pace in and out, now three fingers were going in and out. Then I felt him move closer forcing my thighs wider apart. "Raise your ass higher my little sissy"he ordered. I was so excited by his pleasuring my pussy, I obeyed. I then felt him start to rub with his cock where his fingers had been all around the entry to my pussy. I gasped. "No, not without a condom"and tried to squeeze my ass closed. But he whispered. "My little sissy, the first time you have to take my naked cock, it will be so much more exciting especially for me. I need to fuck you bareback the first time so you can feel the skin of your Daddy's cock inside you.". He held me down with one hand and I felt him thrust his cocked past my protesting sphincter into my pussy. I moaned "No, it hurts." i felt him put both of his hands on my hips and he withdrew his cock and slthered it with more lubricant. Then he grabbed my hips tightly and shoved his cock in deeper ignoring my cries. "Oh , your pussy feels so hot and tight. I love fucking tight pussies. I'm going to enjoy taking your cherry my little sissy Bobbie. Stop struggling. You are going to want it after you relax." With that, he shoved his cock in so far I felt his balls slap my ass. "Now I'm going to really start fucking you, Bobbie. You told me how much you wanted to service my cock. I love fucking little sissies. I love the look in their eyes when they finally see their Daddy's cock and accept their destiny as a pussy there to pleasure their Daddy. I love being the first one to take your ass. It's mine isn't it Bobbie." Yes Daddy" I whispered. "My pussy is all yours. Please fuck me and make me your own sissy." With those words he began fucking me with abandon and as his big manly cock started to be shoved in and out of my pussy and I was forced to relax and accept more and more of his manly cock, my little clit which had shrunk with the pain started to grow and throb with excitement. His cock was rubbing shaker my prostate bringing me closer and closer to orgasm. I was moaning with excitement as he called me his own little pussy slut. I could feel the sheet under my little cock geting wetter and wetter with my pre cum. Then, I shuddered in the wildest orgasm I ever experience. As i did my sphincter grabbed his big cock tighter, it pulled him into orgasm and I felt his cock pulse and start to shoot cum deep into my cunt. "Oh yessssss I own your ass now Bobbie." he yelled. He shot so much cum that it started oozing out of my cunt and running down my thighs. Finally I collapsed into a puddled of his cum and mine. I had never been so aroused in my life.

The next day my wife returned. I was still in a daze from all the sexual excitement of the previous day, but resolved not to repeat what i had done. But when I thought back to how I had been dominated and how excited that made me, the desire started to rise up as did my little cock. Then, that afternoon, Dan, my neighbor, called. "Bobbie, I have a cock that needs some attention, Now!.". I lowered my voice to a whisper as my wife was in the next room and I was afraid she might hear Dan's voice. "Please, Dan, I can't. My wife is home." "Get your ass over here now or I will be over there. You wouldn't want that would you Bobbie, would you?" "Ok I whispered." I shouted out to my wife "I'm going for the afternoon. I won't be back until after dark" "Ok honey, I'm going out by the pool to sunbathe." she answered. When I arrived next door, Dan was waiting standing at the doorway with his pants unzipped and his cock hanging out exposed. I was speechless but thankful that his doorway was hidden from the street. As I stared at his cock, I could feel the desire rising and my little cock start to rise in excitement. "You want it, don't you Bobbie. I can see the desire in your eyes. Can't keep your eyes off it can you, Bobbie? On your knees, now! ". I was overcome with desire to obey him. I could not control my excitement at his treating me like a slut and I knew I had to have that succulent cock in my mouth. My mouth started to water in anticipation as I sunk to my knees and ovaled my mouth. I had to suck that cock again, just one more time I thought. I raised my hands to hold on to Dan's hips and starred at his enormous cock bobbing inches from my watering mouth. I ran my tongue around my lips to wet them and make them nice a slippery to enhance Dan's pleasure and slipped my lips over that huge head. The head filled my mouth and I eagerly began sucking more and more into my mouth until the cock hit the back of my throat. As I pulled my lips and mouth back up his shaft, I kept sucking as hard as I could and I heard Dan say "Ohh yes my little Bobbie, I can feel your desire for cock through your mouth. It is nice and hot just the way a natural cocksucker's should be. You love the taste of cock, don't you? I am going to breed you into a cocksucking sissie by feeding you cock every day. ". His words so excited my that I ran my lips and mouth up and down his shaft up to the cock head and down to his balls all the time sucking as hard as I could trying to make that cock so excited. I force the cock into my throat. "Now my little sissy, start humming on my cock to make it vibrate. That's what a real pro sissy cocksucker can do.". And I started to hum and slurp and suck so I could taste his cum again. His precum started to leak out into my mouth. The taste drove me wild with lust. I sucked and slurped even harder and faster. I wanted his cum. I needed it. I felt him grab my hair and he started thrusting harder and faster, using my mouth for his pleasure. "ohhh Bobbie I am am going to plant my seed in your little tummy again. Oooooh yes". His cock spasmed and his cum spurted into my mouth so forcefully that I started choking and his cum flowed down his shaft. I could not swallow it all and it ran down my chin. When his cock started going limp, he withdrew it and wiped my face with the last of his cum.

"That's a good little sissy. Now let's go upstairs and get you dressed in a slutty outfit. He took my hand and led me upstairs to his bedroom, where he led me to a closet filled with panties baby doll slips and sexy outfits. He reached in and picked out a pair of fishnet stockings, black silk panties and a baby doll see through. I stripped and eagerly drew on my fishnet stockings that showed off my sexy legs, stepped into the black silk panties with a ruffle that hung down over my ass and put my arms into the sexy see through baby doll. Dan ordered me to sit on a bench while he coated my lips with red lipstick. Then had me put on eyeliner and eye shadow. Then as he passed the window that overlooked my backyard, he stooped and stared out the window and saw my wife sunbathing on her stomach with her top untied. She often did that because our yard was very private with high fences all around. Our house an Dans were the only ones on the street. The house also backed up to woods and only one window of Dan's house was positioned so you could see into the yard. "I want a piece of that ass. Bobbie, how would you like to see her with her lips wrapped around my cock? ". "No way, she would never do that. I can't even get her to suck my cock" I replied. He laughed and looked down at my little cock that was obviously aroused at the thought. "I tell you what my little sissy, you watch from the window. You are going to see what she does when she sees a real cock. He pulled on a pair of shorts so brief and tight that you could not not notice the outline of his cock. He shoved his hand inside his shorts and rearranged his cock so the cock head peak out obscenely. "I guarantee she won't be able to keep her eyes off this baby especially after years of dealing with your little cockette.". "She will not. She will just get up and tell you to get lost". I said in reply." With that he led me over to the window and sat me down and gave me his binoculars. "Sit your sissy ass down, Bobbie and watch what happens when your little wife catches sight of a real cock. I guarantee after putting up with your little clit, she will get so excited by seeing a real cock, she will lose all inhibitions and become just as slutty as you became." He was so certain, that I felt myself getting very aroused at the prospect of her seeing the very cock i had sucked just minutes before that I turned to the window aware that my little clit was starting to get wet with excitement. She couldn't really do it. She would be shocked and revolted at the sight. She would storm back into the house. But I was drawn to the window. I heard him go downstairs and heard the door open and shut. Then I saw him walk across his back lawn and open the gate into my backyard. My wife must have been asleep for she did not rise at the sound of the gate. I watched as he sqatted down beside her with his thighs spread apart. Her face was turned towards me. Through his binoculars I could see her open her eyes and as she caught sight of his cock, her eyes opened wider. But to my surprise she did not turn away or get up. I could not hear, but he was talking to her. The conversation went on for some time during which time she seemed to spend more time looking at his cock than his face. Then he seemed to say something to which she nodded in answer. Then he reached down and took some lotion from the side table, leaned over her and started rubbing lotion on her back. I saw her eyes close and she seemed to squirm down on the lounge. His rubbing seemed to be turning into caresses. I noticed she kept opening her eyes and they seemed to focus on his cock and then closing them again. I was stunned that she had not stopped him and returned to the house, but I was so excited I took my clit out and began rubbing the precum all over it which made it flow even more. Then he moved to the foot of the lounge and started to massage her feet. He moved his hands up to caress her thighs. When I saw him start to massage her inner thighs, I was amazed to see her press her pussy down on the lounge. Her mouth opened. She was clearly aroused. Then Dan move to the head of the lounge. He was facing me as he dropped his briefs to the ground and rub his cock so I could clearly see that he wanted me to see he going to take my wife's virgin mouth. He turned and knelt down in front of her head and down began massing her shoulders and back again running his hands all the way down her back until he reached her bikini bottoms. He did not hesitate to move his hands under the bikini briefs cupping and caressing her ass cheeks. I was so excited I started caressing my little clit even more and my ecitement had caused me to put out so much precum that my silk panties were soaked with precum and my clit was wet and hard. I was completely aroused to see my wife about to taste her first cock. I saw her open her eyes and raise her head so that she could see his now erect cock inches from her mouth. Then he brought it forward until it was just before her lips. I could see her open her mouth and flick out her tongue to touch his cock head. She tasted it and leaned forward to capture his cock head but I could see him draw it away teasing her. Then I saw him thrust his hips forward and I saw my wife's mouth bulge outward as she suck his glistening cock into her mouth. As she was sucking, I saw her reach down with one had under her belly to her pussy. She raised her ass and it was evident she was fingering her pussy which must be aroused and swollen and wet. But Dan reached down and stopped her from stroking his pussy. Then he withdrew his cock and rolled her over on her back. She spread her legs. I could see her pussy glissening with wetness. Dan walked around and climbed on top of her. He rubbed his cock on her pussy and then moved up so that his cock wet with her pussy juice was on her lips . I could see her bend her head to lick and taste her own pussy juice something she never allowed with me.. I was in such a state of arousal that I was on the edge of a tremendous orgasm. He moved down and grabbed her hips raising them off the lounge and started fucking her cunt, pounding her ass into the lounge. I was so overcome with excitement that I came in a shuddering orgasm spilling my cum all over my panties and baby doll.