On the all too few occasions that my wife is out of the house over night, I pull out the dildos, mine and hers. I'll dress in my sexy lingerie and play with my ass. She has on a couple occasions, fucked me with her strap-on dildo or we each take an end of her double-headed dildo and bump asses. These have been the only times my sissy ass has received any attention other than from myself since we married over twenty-five years ago. I do love my wife and our sex is great, but I also miss the feel of a hard cock spreading my ass hole wide open. During the rare trips out of town for business, I take a bag full of lingerie and latex cocks to keep me company in the motel room. Since none of my dildos has a suction grip, I have to duct tape them to a table or chair leg when I back up onto or sit down on them.
The first time I fucked myself was at age sixteen with a miniature baseball bat. It was late in the summer. Rob was getting ready to head off to his first year of college. He was leaving the next week, so I was going to let him fuck me once more before he left as my going away present. The weekend was our last opportunity. Our parents and youngest brother were going to be gone visiting family, Saturday into Sunday. Phil was already back at college. We had Saturday night to have our affair. I would later find that it was to be our last time together.
I went into Rob's room Saturday afternoon. He was getting dress to go out for awhile. I walked up behind him as he was pulling up his jeans. I reached around and gently pressed his cock while it was inside his jockeys, back so he could snap and zip-up. He asked me if I was "up for anything tonight." I told him I was, and to be back early. Rob said that he would be in around ten. I told him I would be waiting. He asked what I planned to be wearing.
I said "you'll find out when you get home."
I walked out into the kitchen, where mom was sitting, sipping a cup of coffee. I asked her when they were leaving. She said in about an hour, at five o'clock. Mom asked what I was planning to do tonight. I told her I was going to be working from five to nine, then stay home the rest of the night. I worked at a local grocery store after school and on weekends. That's where I made my money to buy my sissy undies. She asked if I knew what Rob had planned. I smiled inside knowing that he would likely be fucking my ass later, but told her that I thought Rob was going to be back early. Mom said for us not to get into any trouble. I assured her that we would be good.
I said goodbye and went to my room to get ready for work. I decided to wear a pair of red panties on for a thrill. This would be the first time that I would wear panties under my clothes at work. I figured that the only way anyone would know I had them on was if I split my pants. I would find out later that someone at work did know I was wearing panties. But that's another story.
After an uneventful evening at work, we closed and cleaned up. We were out of the store in record time. I just about ran the three blocks home so I would have as much time as possible to prepare for Rob. It was about nine-twenty when I got home.
After a shower, no time for a bubble bath, I dried then dusted myself with some of mom's body powder. I knew I would smell nice with the powder. As I dusted myself I thought how tough could it be to paint my nails. I wanted to be as girly as possible tonight. Naked, I went into mom's room and pick a bright pink nail polish from her vanity. With a towel around my neck and the bottle of nail polish in my hand, I headed to my room to do my nails. I had never tried to paint my nail before, so I knew it wouldn't be easy. I placed my left hand on my thigh as I sat on my bed. I tried hard to be neat, but I had a few mistakes. After finishing, I dropped the bottle on the floor, then blew on my fingertips to help dry them.
I now had about fifteen minutes before Rob was to be back. Gathering up the things that I was going to wear, I walked naked to Rob's room. As usual his room was a mess. I dropped my lingerie on a corner of the bed, the only clear spot. Next I turned on his radio for some rock music, and his table lamp. Placing a towel over the shade to soften the light. I began to pick up most of his clothes that were scattered throughout his room, and piled them in a corner. Smoothing out the bedcover and prepared to dress.
I picked up the garter belt, placed it at my waist then hooked it behind me. Sitting on the edge of the bed, I rolled my white stocking in my fingers, checking to see if the polish was leaving any marks. They were fine. After slipping both nylons on, I stood up to attach them to the claps. This was always my favorite part of dressing. The tug of the stockings on the garter straps was always a big turn-on. The straps brushed teasingly against my thighs and bum. What a great sensation it was. I picked up the pink satin camisole and slipped my arms through the spaghetti string straps. It was the first time that I had worn it since buying a month ago. I thought it felt a little snug, but it looked fine in the mirror. The last piece of my outfit was my tap pants. I stepped into them and pulled them up my stocking covered legs. I loved the look of my painted nails sliding my pants up to my hard sissy cock. My boy boner bobbed in anticipation. I tucked my girly cock back so I could pull the waistband up over it. With a piece of pink ribbon, I pulled my hair together and tied it back. Looking into the mirror, I saw a feminized me looking back. I did a few sexy poses, bending and sticking my bum out while I waited for Rob. I was horny as hell.
It was about five after ten when I heard the back door open, then closed and locked. I stepped to the bed, pulled back the cover and sheet and jumped in. Pulling the covers over me, I smoothed out the spread and pulled my arm under, Rob popped his head in the door. He saw me laying in bed and smiled.
He said "great, I'll take a shower and be back for my present."
As Rob walked to the bathroom, he sang a verse of a Led Zeppelin song " way-down-in-side--woman-you-need-me." He sang it loud enough so that I could hear him. If I had known he was going to shower, I would have waited and showered with him. I would have soaped him up all over. I was ready to get undressed and join him, but decided not to. I could entertain myself while I waited.
I couldn't wait to have something up my bum. I reached my hand down to caress my satin covered cheek. While rubbing my bum, I noticed a miniature wooded baseball bat on Rob's dresser. A souvenir from a Pirate game we had gone to. It looked to be about the same diameter as Rob's hard cock. I had one just like it in my room, but his was black. I hadn't thought of it as a sex toy before, but I was now. I figured, "wonder if it would fit in my pussy hole." I could loosen up before Rob got back. I got out of bed, grabbed Rob's jar of gel and picked up the bat. I took off my tap pants, greased up the fat end of the bat and my hole. I leaned down, reached back and tried to work it into my tight bum hole. It was tough trying to get it started in. I needed something to rest the other end against. I moved to Rob's weight bench that was at the end of the bed. Trying again, the bat still moved around too much. I picked up two twenty pound weights and stacked them on the bench. Putting the skinny end of the bat in the holes, I could now begin to work the fat end in my pussy. I knew I had to move quickly if I wanted to be in bed when Rob got back. I took a deep breath and pushed down on the slick bat. My bum hole gave way and the bat began to slid inside. I got it in an inch of two, then the burn hit. I was bent over while leaning back on the bat. I had to stop for the pain to pass. The bat felt bigger then Rob. It did not have any give, like Rob's rubbery cock does. I thought, "this was the first time I had a real woody in my ass." I pushed down some more forcing a couple more inches in. I wiggled my bum around, the bat was gripped tightly by my muscles. I reached back around and grabbed it as it came out of the weights. Pulling and pushing it a couple times, I loved the fullness. A few more pumps and I felt loose enough. I was running out of time. Pulling the bat out, I tossed it onto the piles of clothes. I would clean it later. After a quick wipe of my bum with the towel, I pulled my tap pants on and jumped back in bed.
I relaxed a bit, then heard the bathroom door close. Rob was heading back, singing his song again. I checked the room to be sure that everything was in place. Rob opened the door and walked in naked. His six-inch cock was as hard as the bat that had just fucked me. He had a towel around his neck, which he laid on the bed.
Rob said "I want my present now."
I asked him to turn the radio down lower. After he turned away, I flipped the covers up over my body, exposing my pink satin outfit. As he turned back around, I said "here it is." Rob stood looking down at me smiling.
He said, "that's what I was hoping for."
I told him, "there's more once you unwrap it."
I reached out and grabbed his boner and pulled him to the bed. Rob got in bed and laid down on his side facing me. His hand reached out and slid along my satin cover hip and bum. Rob ran his hand down below the leg of my tap pants onto my bear thigh and tops of my stocking. The sexy feel of my body when I dressed in my sissy lingerie, drove Rob crazy. He caressed me. His hand slid along my satin wrapped body. I laid my head on the pillow and closed my eyes for a minute. I loved the attention Rob was giving me, but this was his night. I wanted to pleasure him tonight.
I grabbed the covers and sheet and pulled them up over us. Ducking my head down under the covers, I slid down the bed until my face was at his waist. With a hand on his hip, I pushed him onto his back. As I did I sucked his cock into my mouth. I adjusted my position as he rolled back. With my mouth locked on his pole, I twisted around with my bum towards Rob's head. I straddled my arms over his hips. My face hung over his balls. My nose poking his sack as I lowered my lips along his shaft. I would, after a few bobs, nuzzle his cock against my cheek and nose. Tuck my nose between his sack and thighs. I loved to rub my face in his crotch, especially after he had showered. Rob smelled fresh and clean. I lapped along his shaft. Teasing him by flicking my tongue at the underside of its head. Then licked the drops of pre-cum from its tip. The tip of my tongue wiggling into his cock hole. I nibbled on his rubbery head. Lightly scrapping my teeth across its spongy flange. Then I got carried away and began to nip at his helmet head.
Rob lightly slapped my head through the covers and said "Christ, take it easy, you're gon'a draw blood." I mumbled an "ok" as my mouth slid down on to his cock.
I went back to sucking Rob's tasty cock. Dressed in my outfit, bobbing under the covers, I felt like a real slut. I did a slow, easy motion on his shaft. As I swallowed his boy bone, Rob placed a hand on my bum. He began to make small circles over my satiny cheek. I wiggled my bum slightly, showing my approval. He continued his caressing, slipping his hand down between my legs, along my stocking, to my knee. When he brought his hand back up along the inside of my bear thigh, they tugged on the garter strap. His fingers slid in the leg opening up to my balls. He diddled my sack. Rubbing and tweaking my bag and balls.
I stop my attention of Rob's cock and lowered my face into his crotch. My focus was now on what Rob's fingers were doing. After a few seconds of nuzzling his sack, I resumed my mouth fucking. I was as horny as I had ever been. I gobbled his boner like a starving man eating a hot dog. He would lift his hips off the bed at times, trying to force more of his cock down my throat. I sped up, then slowed down my sucking, building his anticipation. Rob's hand moved from my sack to my sissy cock. His fingers wrapped around it, sliding along its stubby length. Rob wasn't into guys, but he knew what felt good. He tried to give me some pleasure.
We each continued to service the other. Rob, slowly jacking me off, while I stuffed his cock into my hungry mouth. Rob's hand then moved away from my aching sissy cock. His body was shifting around, twisting onto his side. I could hear him reaching for the jar of gel. I figured he was going to finger my bum hole. Once he had a hand full he laid flat again. Rob's hand slid back under the covers. I waited for his fingers to start poking at my hole. Instead, his gooey finger wrapped back around my boy clit. It was cool but nice. His fingers lightly slid over my cock. It wouldn't take much for me to blow my load. I was working his cock faster with my mouth. His point of release was also approaching. I wanted his first shots of the night to be in my mouth. I hadn't expected him to pump me to climax. But now I wanted us both to explode at the same time. Rob's jacking on my cock had me at the edge. I sucked him faster and deeper, his moaning began to grow lower and more often. His stroking of my clit was getting irregular. I knew we would both be shooting soon. My tongue rubbed his cock head, coxing his warm sticky cum out of his sack and down my throat. My juice started to boil. My sissy balls began to pump out my sticky cream. Goo shot onto his fingers and hand. Meanwhile his cock erupted inside my mouth. Jets of thick, salty cum filled my cheeks full. I let out a low "ummmm" while swallowing as much as I could. Some oozed out the ends of my mouth. I would clean the drips up later. My blasts of boy juice coated his hand and the crotch of my taps. That was ok, I planned to take them off once Rob finished feeding me his seed soup. As we both emptied our balls, our tempo slowed a bit. He kept stroking my clit, draining the last of my juices out. I tightened my lip grip on his shaft, sucking out as much of his cum as I could.
We were both drained and satisfied. But I wanted Rob to stay hard for a second round. I kept my mouth on his semi-hard cock. Using a soft grip, I slowly slid along his length, moaning as I bobbed up and down. Rob had released his hand from my sticky cock. He wiped his hand clean, while I reached back with one hand to work my pants off. I got the pants partly off my hips. Rob brought his hand back under the sheets to my ass. Sensing my intention and difficulty doing it, he took hold of the waistband and helped pull them down to my knees. While still wet from cum, Rob carefully slid the pants along each leg as I lifted up to get them off. Once they cleared my legs, Rob tossed them onto the floor. I felt naked even under the covers. Rob used the towel to tenderly wipe my cock and sack clean.
With Rob's cock still in my mouth, we laid still for a few minutes, enjoying the afterglow. But now I wanted to get fucked. I started to work on getting his cock stiff again. I slowly bobbed my head on his shaft. Rob thought we were done.
He asked me "aren't we finished yet?"
I mumbled "no" into his cock head. "That's only half of you gift", I said with half of his cock still in my mouth. I continued to pump his shaft with my lips. My one hand lightly rolled his sack in my fingers.
Rob said "I'm up for what ever you have in mind." I told him to "grease up my pussy." He reached for more gel, than began to smear it over my rose bud.
Rob poked a finger in, expecting some resistance. But it slid through with no trouble. It felt like my pussy sucked it in. He added a second finger, then a third. As each was added and slid in with ease, Rob worked them deeper. After the fourth went in, he started to hand fuck me. Pounding in my pussy, he forced my body forward, but my lips stayed tight around his cock. I was pushed from behind as his fingers drove in. Then leaned back as he pulled out. I was being sodomized by his whole hand.
Rob asked "you're pretty loose. Do you think I can get my fist in?"
I lifted off his cock and told him "Go ahead and try. If it starts to hurt, you'll have to stop. Besides it might be too loose for you after."
Rob said "that's true. I think you're ready."
I was ready. I kissed his cock head as I moved away. I threw the covers up off of us. The cooler air was refreshing. Under the covers it was quite warm, but I hadn't noticed how warm until now. Reaching up across Rob, placing a hand on his chest to steady myself. My soft sissy cock, rubbed against his cheek. He turned his face and stuck his tongue out, teasingly licked my head. I intentionally took my time scooping some gel up, giving Rob time to lap me more. After a few seconds of Rob's tonguing, I moved towards his cock. With my hand full of gel, I stroked his boy bone. I coated his shaft and head, making it slick and shiny. Then pumped him a few times, until he was nice and stiff. The sounds he was making told me he was ready. Shifting myself down beside his hip, I let go of his cock as I wiped excess gel on my bum hole. With my back to him, raised a leg up and over. I straddled his hips, my pussy just above his slick head. I reached between my thighs and held his pole steady. Slowly lowering my bum down until its greasy entrance touched his tip. Not wanting to wait any longer, I sank down on his cock. My pussy swallowed him like my mouth had done earlier. My cheeks were pressing down hard into his hips. It felt like it belonged inside. I placed both hands on his knees, leaning forward. In this position I could rock back and forth on his shaft. Doing a slow steady ride. Rob placed his hands on my hips, his fingers tucked into my garter belt. I rose up an inch or two then back down. I stopped moving, holding his cock prisoner. His cock head twitched inside, as I threw my head back, letting out a groan.
I was content to sit like this all night, but Rob tried to buck up into me. Lifting his hips off the bed, along with me. I got the message. I began to bounce on his pole. My cheeks left his hips, as I raised up, then dropped back down. It felt lovely. I rode him for a few minutes, keeping up a steady motion. Rob pulled down on my belt as if to impale me on him deeper.
My legs were cramping up from being tucked under my ass during all this. I suddenly raised up off Rob's shaft. He was pissed.
He said "what the hell are you doing."
I told him about my legs. I said "I need to straighten my leg out. I thought, if I can extend them I would be fine."
I told Rob to swing his legs around drape them over the side of the bed, placing his feet on the floor. I moved off to his side, he muttered and moved as I suggested. Once he was in place I stepped onto the floor, spread my legs then backup past his knees, on over his thighs. Lowering my bum a bit, until I felt his twitching cock at my crack. I slid up until the head aligned with my pussy. I sank down onto him with no effort. I was so loose I think I could take his fist now.
I was sitting on Rob with my stocking covered legs rubbing against his thighs. I quickly started to ride his shaft up and down. Rob was laying flat and again reached for my belt. He tucked his finger in so that his hands could keep up with me. Bouncing off his thighs, it felt like I had springs in my ass. A squeal slipped out of my throat, surprising me. It sounded like a girl. That was the first time for that.
As I pounded down on Rob's cock, I noticed his hips and ass were sliding off the edge of the bed. This wasn't working as well as I had hoped. I stopped fucking him.
"What's wrong now?" he demanded. By the tone in his voice, he was getting frustrated.
I said "your sliding off the bed. We need something under your ass."
I saw his weight bench. Leaning over, I grabbed for the leg, wanting to keep him inside if I could. Stretching until he was about to pop out, I got a finger around the leg and pulled. It didn't move much, but enough to get a couple more fingers on it. The two twenty pound weights were still on it, which made moving it harder. Once my hand was on the leg, I tilted the bench until the weights slid off.
Rob raise his head up and asked "can you make anymore noise?"
I said "just get ready to be fucked to death ."
Still with Rob part-way in, I slid the bench over to us. I told him to spread his legs and lift his hips up. With both hands, I worked it under him until it was against the bed. As much as I tried, Rob's cock popped out. We both let out a groan. But we would be back to fucking in seconds. The height of the bench to the bed was pretty close. I asked him how it felt. He said "fine, lets go."
Knowing this would be our last affair for a while, I wanted this one to be special. I again backup to his swollen cock, as it pointed straight up. The head wedged between my bum cheeks, I raised up, sliding it along my crack. When the tip touched my pussy hole, I stopped and held still. I wanted to tease him. Pay back for the times he teased me. But Rob would have none of it. Sensing my wanting to draw the action out, he lifted his hips, ramming his cock half way inside. He held himself up until I drop my pussy down, swallowing it completely. When he laid back onto the bed, I rode him down. We both groaned our satisfaction. I leaned forward, with my hands on his knees again. Rocking on his hips, this time I knew nothing would stop us. I rolled forward and back, my cheeks never leaving his thighs. Rob laid quietly except for a moan every so often as I rolled back, driving his boy bone deep up inside. At times, with him buried to the root, I would stop and set motionless, my head back, eyes closed, enjoying the sexy feel of his twitching shaft. My pussy encircled it lightly at the base like my lips did while milking his sack dry.
Once I had my fill of silent, soft fucking, I was ready for the loud, hard fucking. Without warning, I rose up until his head was nearly out, than dropped hard down. If he didn't know then, Rob knew soon that I was ready to finish him off. I quickly rose up and down, repeating my motion again and again. I was letting gravity do some of the work, shoving his head as far up as possible. I got into a rhythm, raising up and dropping down. Rob didn't move a muscle, except his lovely cock. I took my hands off his knee and placed them to my thighs. I caressed my stockings wrapped legs Lost in my sissy lust. The sex was great, but without the lingerie, I probably would not have been as interested in sex. The first time when Rob stuffed his cock in my mouth, while I was asleep, was a complete surprise. But when I got to dress in satin and lace, I would do just about anything. I may have resisted Rob's second advance if he hadn't dressed me in mom's panties and slip. But as I fucked myself on Rob's six-inch college cock, I was loving it all.
I bounced on Rob for what seemed like an hour. My cheeks making a slapping sound, like my ass was being paddled. I was ready to drain his sack of every drop of his warm juice. I could hear squishy sounds coming from my bum. My speed increased until the bed and bench were creaking wildly. I was afraid the bench might not hold up. It twisted and racked with each of my down motions. Rob was grunting like an animal on the edge. He was getting close to releasing into me, and that's just what I wanted.
Rob grabbed my garter belt, pulling me down and held me there. He tensed up, lifted his hips and exploded into my pussy. He cum geyser shot a warm stream up inside. He bucked up a couple times trying to force his goo even deeper. The feel was heavenly. I did a slow rock back and forth, milking Rob's pole with my pussy. He kept pumping but his jets were lessening and becoming weaker. His second time of the night didn't have the intensity as the first. But I was completely satisfied now. I let out a soft low groan as I accepted his last pulses of cum pudding. My skin was damp, from the workout we had just gone through. My cheeks were stuck to Rob's tummy by the sweat and our juices.
Rob released the waist of my garter belt, his arms dropping to his sides. His cock went semi-soft inside. I leaned forward letting him slip out from my well fucked pussy ass. My stretched open pussy hole began to leak thick ooze onto Rob's sack. Lifting a leg up over Rob, I slowly stood up. My legs were weak, sore and shaky, but I was happy. Cum ran in a slow stream down the back of my thigh, into the top of my stocking. As I reached for a towel, I turned to face Rob for the first time. His cock and balls were a gooey mess. He had a puddle of cum in his pubs. As he shrank, I lifted and wiped his parts, being sure to do a good job cleaning. I also was hoping my attention of him would maybe get him hard again. I would have been willing to go at it again after a short rest.
After he was cleaned, he said that he was wasted and ready for bed. I moved his legs so that I could slid the bench way. Once it was moved, Rob raised his legs and swung them on the bed. He rolled onto his side, his bum sticking out at me. I stepped to the side of the bed, patted his bear butt then pulled the covers up over him.
He was asleep before I finished picking up. I found my gooey taps, stepped into them and pulled them on. I felt like a well-fucked slut now. I was tired but I needed to take a long, warm bath. I turned off Rob's light and walked out. Rob got his gift and so did I.
When Rob came home during his first semester break, he told me, he had decided that he wasn't going to chance getting caught screwing me. Besides, his attention was completely on girls.
Even my late night blow-jobs were over. I use to sneak into his room while he slept. Wearing a pair of panties under my robe, as carefully as possible, slide the covers until I could nuzzle my nose into his crotch or bum crack, which ever was accessible to me. He would just laid softly moaning and raising his hip as I swallowed him until he fed me his milky juice.
He said what we did was experimenting. He was now over that kind of sex and we were not doing any of that again. I was a little hurt and disappointed but was ok with his decision. Besides I was getting better at fucking myself with things I found around the house.
I did get fucked again, but by someone else. I'll write about that soon.