My love of lingerie during my early teen years was directly responsible for my first sexual experiences. But the sex was not with a girl, but with my brother Rob.
I loved the look of a girl's ass in a pair of skin tight jeans. The sight of long legs with the ass cheeks peeking out from the edge of a pair of short cut-offs made my teen dick hard. I did love girls, just that I was too shy to approach them. After my first sissy ass fucking, dressed in mom's panties and bra, I wanted to do it again. I was always thinking of sex, so sex with Rob would be my release.
About a month passed since our first dress-up sex. I wasn't sure if there would be a repeat. The coming weekend, my parents were going away with my younger brother. My older brothers, Phil and Rob, went out Friday night. I stayed at home to see what might happen.
Nervously I sat watching tv, waiting to see if Rob would want to fuck my sissy ass again. I loved it when I was dressed up in sexy underthings. Being treated like a girl was what I wanted.
At around eight-thirty I heard someone come in the front door. Rob walked in, looked around the living room, saw me alone, then went to his room. Minutes later he was back out, going room to room checking to see who else might be home. After he was satisfied that we were alone, he entered the room and said to me "lets go". As if I had no control, I hurried up off the chair and followed him in to our parent's room.
Rob pulled out my mom's lingerie drawer, and started to search through her silky undies. Rob picked up the same things I wore the first time. I moved beside him and said, "no, I wore that the last time. I'll do what ever you want, if I feel sexy. So let me pick the things I want. If I'm happy, I'll make sure your happy". I wanted something sexier this time. Rob looked at me with a slight grin, and dropped the panties and slip. As I nudged over to the middle of the drawer, he stepped back and sat down on the bed.
I began to run my hands through the piles of nylon, satin and lace, wishing they were mine. As I pulled items out, I would hold them to my waist to see if they might fit. My mother was shorter then I, but had wide hips and large breasts. I did not have a girly body but I could wear most of mom's things. It was the perfect age for me to be sissy dressing in an otherwise all male house. I had no sisters to raid their panty drawers.
I then found a pink bra I liked, and a pair of matching satin panties. As I searched for something more, from behind me Rob said "strip down". I told him I wasn't finished yet. He said "you can look after you take your clothes off. I smiled and put the things down. As I took off my shirt, I could see Rob behind me getting undressed in the mirror on the dresser. He was out of his pants and underwear in a flash. I dropped my pants and as I was stepping out of the legs, Rob was grabbing my jockeys and pulling them down. He then reached and squeezed one of my ass cheeks, with his thumb in my pussy crack. My cock was standing straight out, in the mirror I could see Rob stroking his sixteen year old rod. He was horny and so was I. Rob stepped up behind me, pressing his warm naked body against my backside. His cock was bobbing at my butt crack, smearing precum on my cheeks. Rob's hands on my waist pulling me in to him. He then reached around me and wrapped his hand on my girly cock. I could have shot my gooey load all over mom's open drawer. His middle finger slid to my cock head and he began to finger my cock hole. Rubbing drops of ooz over its head, I was weakening. But I wanted to be dressed in mom's silky things before we started. I pushed him away from me and told him to go sit down, so I could finish my selection. Rob sat back down, and with a demanding voice said "hurry up, we don't have all night". He was right, we could not lose track of the time. Phil would be out for a few more hours, but we could not have him surprise us by coming in earlier. After a few seconds more I grabbed a garter belt and white nylons to complete the set.
I picked up all my pink things and put them on the bed between us. I pulled the satin bra out from the pile, held it up to my nose and inhaled the smells. Then reached out my arms and to put it on. I sled my arms through the straps loops, grabbed the clasps and pulled them to hook them. As I did Rob reached over and tickled my balls as I struggled with the bra. I wiggled away telling him to wait. We both couldn't wait but I wanted to be dressed up.
After hooking the bra, next came the garter belt. Rob looked at it and said, "Why do you need that?" I told him to relax, that he would like the finished look when I was done. I hurried and hooked it to my waist. I was really starting to feel sexy with the clasps dangling down my thighs and ass. Next I sat down and took a nylon in my hands with the thumbs inside. I'd seen women in the movies do it this way. I gathered it up until the heels were at my thumbs. Bent over and slowly stretched it up my leg, careful not to rip it. After it was attached at the clasps, I then worked the other on and fastened it. I could feel my cock throbbing from the building excitement. My first garter and nylons what a slut I was. As I stood up to put on my panties, I felt the sexy tug of the nylons on the garter straps. The feeling was heavenly, I felt like a slut now. Rob told me to turn around. He wasn't completely in to the dressing up part, but he knew I would cooperate easier if I got to dress up. He just wanted to get to the sex.
Last came the pink satin panties with lace trim. I bent down and held them out to step into them when Rob asked, "why didn't you put them on before the nylons are hooked up?" I said that with them on the outside I could take them off without the nylons getting in the way. He nodded his approve. I pulled the panties up over my stiff sissy cock. They didn't fit well with my cock poking out from inside. I wanted a more girly look, so pulled my cock out of a leg hole and began to rub along the shaft. Rob asked what was I doing, I told him I didn't want my cock to show. Still standing, I continued to pump away. Rob slid closer and cupped his hand and reached out just beyond my cock. I started to pump harder and faster, totally loving the feel of my sexy things. I roamed my free hand over my satin covered ass and fingered the garter straps. My point of release was approaching. I moaned softly, closed my eyes and tilted my head back. I shot load after load from my sissy cock, until my balls were empty. I was spent and sat down on the bed. Still shaking with tiny spasms all over my body. With my head back, my eyes still closed, I felt something wet hit my lips. I opened my eyes quickly to see Rob's hand above my mouth dripping my own cum on to my lips. I kept my mouth closed until the gooey warm cum ran down to the corners of my mouth. Rob said, "open up". I opened my mouth and let the sticky juice hit my tongue. It was bland and salty, but not offensive. Rob dripped most of the jizzum in to my waiting mouth. When no more drops fell, Rob told me to lick his hand clean. I slurped and licked until it was all gone. I used my finger to wipe the goo off my lips. Stuck the finger in my mouth and licked it all. I did enjoy that. Men have no idea how sexy cum makes you feel. It's warm, sticky and your willing to do anything after you've ate cum.
I wanted to do what ever Rob told me to do now. I stood up and pushed my shriveled girly cock back into my panties, tucking it down between my legs. Now I looked like a girl, and I felt like one. To finish the illusion, I stuffed Kleenex tissues into the bra cups. Mom probably wandered what happened to all her tissues.
While I filled my cups, Rob slid on the bed, laid on his back. His cock standing up waiting for some attention. I did not need Rob to tell me what he wanted me to do. I got on the bed on my hands and knees and straddled over his legs, with my lips above his bobbing cock head. Rob's hands back behind his head, he watched me as I opened my mouth and stuck out my tongue just above his cock. I stayed like that for a few moments as saliva mixed with my cum started to run down my tongue and drop on to the tip of his cock head. His cock twitched when the first drops hit. More of the warm, sticky goo dripped down, running off the head and down the shaft. The fluids reached his balls and puddled between his thighs. Rob's cock was sparkling from the light shining off the saliva cum mix. I lowered my mouth until my tongue was just touching the hole on its head. I flicked it a couple times and licked up some of the salty concoction. Rob moaned, "suck it", but I wasn't going to hurry this.
I moved off of Rob and turned my satin ass around on the bed until my cock was above his face. I told him that I would take care of him if he gave my ass and cock some attention. Rob reached up and began to rub my smooth pantied covered cheeks. I held up my end, so to speak, and lowered my mouth down over his shiny purple head. As Rob's cock slid over my tongue, all the way in, my nose bumped into his smooth wet sack. (We were both past puberty, but pretty much hairless around our balls.) I could have drowned in the puddle of drool juice around his balls. My lips gripped his shaft as I lifted my head up and off. I leaned forward and down to lick the mess between his legs.
Meanwhile, Rob was rubbing small circles, with his fingers over my pantied sissy ass and occasionally would slip his hand between the garter straps and my bare thighs. Rob would trace along the elastic leg band with his fingertips, slip one inside, pull and lightly snap it against my cheeks. It was very sexy.
I cleaned up the puddle around his sack, and went back to sliding my face down and up his tasty rod. I would bob a few times, release it. Then rub my lips, nose and cheeks along its length. I could not get enough, I loved the slippery, silky feel of it as I nuzzled and kissed it all over. I rubbed my lips over its rubbery head, planting soft kisses at the base and balls. I was in love with his pink and purple cock. It was the only thing that mattered to me. I loved it and had to worship it. I moaned with satisfaction as I buried my face in his pubs. I was lost in the lust.
I was concentrating on Rob's cock so deeply, that I did not feel him pulling the leg band over to release my growing sissy cock. Before I had realized it, Rob was darting his tongue up around its head. I now began to moan from the sensations of both cocks being loved. I needed my cock sucked and I had to have Rob's in my mouth. I kept going up and down and around Rob's twitching cock. My tongue started to ache, but I didn't want to stop. Rob was teasing me, by licking and nibbling at my cock head. He scraped his teeth over its spongy helmet head, he was driving me crazy. I would push my hips down forcing my sissy cock passed his lips, then raise back up. We would do that over and over again. This went on for a while, who knows how long. It was good that I had jerked off earlier, I could now last longer before my next release. I want it to last as long as possible.
As we wiggled and moaned, I felt Rob finger the skin behind my ball sack and trace a line to my pussy hole. He fingered the puckered edges, causing me to moan softy into his sack. He then removed his hand. I could feel him moving under me. Moments later his finger retuned to my pussy, this time covered with a cool gel. Rob must have put a jar on the night table earlier for easy reach. He diddled at the tight opening, then press his finger slowly through. It threw off my bobbing rhythm on his cock. I stopped and held Rob's shaft in my mouth, rubbing it with my tongue as he worked his finger deeper in me. I wiggled my acceptance of his invasion of my pussy. It was tight but I wanted more. He pushed in as I pushed back. The pressure was uncomfortable but worth it. When he was all the way in he held it there a few seconds. Then pulled out to the entrance. As he pulled back I leaned forward. I reached back and pulled my panties to the side to allow him easier access. He put a second greasy finger to my butt hole. I pushed back against them. He knew I was ready for more. As the two fingers slid past my "o" muscle, I leaned farther forward trying to adjust to the pressure. But the pain passed quickly, I was starting to relax now. I again leaned back as Rob buried them deep, and then ticked my innerds. He knew I was loving it. He pulled out again and added a third then a fourth finger. When the last finger started in I slumped forward, my face between his legs. My ass was still up in the air as Rob worked my poor pussy hole, stretching and lubing it. He started to finger fuck me. When he pushed in, I pushed my hips back. He would pull out, I would moved forward, careful not to have his fingers leave my pussy completely.
This went on for some time until I moaned out that I could not take any more. I crawled forward until Rob's fingers could not stay in. Rob sat up, I move to the side so he could get out from under me. I rolled on to my back to catch my breath, my head at the foot of the bed. Rob got off the bed and told me to spin around with my head on the pillows. I was weak but I wanted to go on. I got turned around, laying on my back, eyes closed, and my breathing starting to slow. I could hear Rob at the night table. He picked up the jar of gel and got back on the bed. As I opened my eyes I saw Rob coating his throbbing cock with gel. I scooped some gel and reached for his cock. My fingers rubbed a thick coating of goo over its fat head. I teased his cock rubbing and pulling it. I was at a point that nothing could stop me from getting my sissy ass filled by that cock.
As he rubbed the gel around, I stopped and began to turn over on to my hands and knees. Rob stopped me by saying "Don't, I'm going to take you like a girl, on your back". That sounded nice, I would just lay there while he did all the pushing and pulling. I reached to take my panties off, working them over the garter straps, down my nylon covered legs. I got one leg out, but Rob didn't wait for the second. As my legs were off the bed, he grabbed them and pushed them straight up. The panties hanging on my ankle, like a slut flag. Rob moved forward between my silky legs, Placing a calf at each shoulder, leaned forward so that his weight would keep them in place. Rob then slowly slid his hands from my ankles to the nylons tops just above my balls, fingered the garter straps then slid up again. He planted small kisses along my thighs. I loved the attention but I wanted a hard cock inside.
He said " I'm glad you thought of the panties over the garters, they don't slow things down". I nodded and smiled. As he caressed my legs, his hard cock was bouncing up and down on my ball sack. Gel was smearing all over us, his thighs, my thighs, sack and ass cheeks. I reached for his balls and rolled them between my fingers. They were heavy and full. I wanted their juice inside of me. I guess Rob did also. He stopped kissing and teasing my legs, inched forward. Bending my legs up over my chest, my ass rolled up in the air. The stuffed satin bra was tickling my chin. His cock head was resting at my pussy opening. I wanted Rob to push it in, but I was having trouble breathing. I told Rob that I needed air. He stop moving and let my legs drop to his sides. He told me to, "give me a couple pillows and lift you ass up". I tossed them to him, he tucked them under my hips. Rob scooped some gel, rubbed it into my pussy hole, then raised my legs and leaned forward. His cock was aligned with my waiting hole and I was ready.
Rob took hold of his shaft and began to push in. None of my complaining was going to stop him now. I felt the head force its way past my tight grip. It had been a few minutes since his fingers were in so I was a little tense. I wanted that fat cock in now. Rob leaned in to me, sliding his cock head all the way in. I let out a soft "ooooooh". Rob moaned in satisfaction. My pussy was clamped on to his pole. I could feel his cock bobbing inside as he held still. As it twitched around, I was afraid he was going to shot his load, so I did not s move, waiting for his spasms to pass. Rob fought back his urges to release, and began to pull back out. He pulled until the head caught at my "o" muscle. I wouldn't let it get out. He then pushed in. It felt like it was getting fatter and longer. Rob's eyes were closed as he tilted his head back. I would open and close my eyes depending on Rob's grunts and growls. He moved only his hips slowly back and forth bumping my innerds with his cock head. Rob would push in, stop then slightly rotate his hips to make the head wiggle around in me. I could not have been happier, I was a sissy girl getting fucked and loving it.
Rob began to work his cock, slow and steady, enjoying the feel. As he sawed in and out, my muscle massaged his shaft. Rob reached down and pulled on my sissy cock. I lifted my head and looked down. I could see his hand wrapped around my cock, framed by the garter straps and nylons. I smiled inside thinking that this was so great.
After stroking my cock a few more times, he let go and began to concentrate on his cock in my pussy. I did not mind, I needed my ass pounded more then my cock played with. Rob began to pickup the pace, slamming my ass hole harder and faster. He's forceful banging pushed my head into the headboard. I didn't care at this point. I wanted him to pounding away. Rob was oblivious to everything. He only cared about finishing fucking me. I was his sissy fucking toy, that was fine with me. Rob now was slamming my soar pussy with all he had. His hips were slapping hard into the cheeks of my ass, I could hear the smacking sounds. I was pushed farther in the headboard as he fucked me like a man possessed. Rob was moving in and out like a machine.
I was near the end, unable to take much more of the emotions and sensations I was receiving. I felt a pulse at my pussy hole as his cock sank deep into my pussy. His cum was starting to boil out of his balls. He pulled out once more then hard in and stopped. Rob groaned loud and deep, rotated his hips, grinding into my cheeks, forcing his twitching cock as far inside as it could possibly reach. My ass pussy locked on to his shaft, I felt more pulsating passed through my clinched opening. Rob's cum blasted into my innerds, shot after shot passed my pussy hole. I could feel each shot of hot jizzum hit inside. I grabbed the bedspread and stuffed it into my mouth to muffle my moans of pleasure. I stiffened my back and my toes went straight up in the air. It was like a fire hose was opened up inside of me. I was alert to all of my senses. Rob moved little except I knew he was tossing his head back and forth, moaning between each shot he released out. My eyes were closed tight as I wished it would last a little longer.
But of course it didn't. Rob's few remaining jets of cum were spent long before I would have liked them to stop. I wiggled my ass to see if he had anything left. He slid out part way then drove back in, milking the last drops in his vein. Rob slumped pushing my knees almost to my fake boobs. My panties daggling above me face. He took a few deep breaths and whispered, "damn, that was good". That was a compliment to me. He lifted his hips to slowly pull out then back in a few times as his cock shrank some. I was hoping he was going to try and get hard again. I grabbed his hips to hold him in. But he then pulled out completely. My pussy made a sound like gas. Rob made a face at me then said, "thanks a lot, I'm still back here". I told him it wasn't gas. He fucked me so hard that air must have built up inside. I giggled a bit at his accusing look.
Rob rolled to one side as I lowered my legs. I was kinda stiff from being that position for so long. My cock had shrank also. I had no need to shoot my load right now. I could do that later myself. My soar, puckered pussy hole began to ooze Rob's gooey cream down the crack of my butt. I tried to get up before some hit the spread. I was to slow, I was leaving a messy puddle. Rob tossed me a towel that he had just wiped with. I shoved it between my legs to catch the rest. I hopped out of bed, heading for the bathroom. My joints were tight as I shuffled along.
I returned from the bathroom, Rob was gathering his clothes and jar of gel. I stood in the doorway as he headed out. He looked at me and said, " I'm not gay, I just need to get laid once in a while. Since you seem to enjoy it when your dressed in mom's under things, I see no harm in, OK". I smiled and nodded.
As he did the first time we had sex, he said "clean up the mess and don't miss anything if you want to do this again". Rob walked past me, heading to the bathroom. As he went by he slapped my bare ass hard. I yelled out from the sting and surprise. I dragged myself to the bed and sat down to gather my strength. I noticed it was almost eleven o'clock. We had been at it for over two hours. How time flies when your getting you ass royally fucked.
More stories to come.