The Friday after our latest affair, I asked my brother Rob to drive me to the mall. I needed to buy stockings to replace the pair we ruined last weekend that belonged to our mother. Rob brought along a friend, Mike. It was probably better that someone else came with us. It could be awkward, not knowing what to talk about to a brother who's been fucking me. While dress in lingerie, I'm willing to do just about anything. When we're fucking, we don't talk a lot. Afterwards Rob usually leaves right away. I guess we're both not sure that what we're doing is right.
I sat in the back seat while they talked upfront. They discussed which girls in school they would like to fuck. Who had the nicest legs, ass and tits. I liked girls too, but I was busy planning on what I might buy for myself today.
When we arrived at the mall, they took-off together. But before they left, Rob told me to be at the car in an hour and a half. I headed straight for Penneys. I knew from previous trips through there they had prettier lingerie than Sears. Also, mom shopped at Penneys, so I hoped to find her replacement stockings there.
As I walked into the ladies foundation department, my stomach started to flutter. I was finally going to buy my own sexy girly things. There were so many displays to look at. I needed to keep focused on what I wanted to buy. Not to wonder around looking at all the other lovely things.
I first wanted to get the stockings for mom, then I could spend the remaining time on myself. After looking at the different stocking displays, I choose a pair that seemed to match the torn stocking I had brought with me, in my pocket. The size length would have to be a guess. I wasn't sure, but since my mother was about six inches shorter than me, I would get her mediums. I also bought myself a pair of black, like mom's, and a pair of white stocking. I got mine in size tall.
Now I could browse around for my other things. Next, I wanted some panties. I had checked mom's panties to see what size she wore. Hers were size seven, I would buy size eight. They would be less snug I figured, that way my sissy cock could slid around in them. It would feel much more sexier. My budget was limited, so I would have to find some bargains. I found a bin with a sign that read "4 for $6.00". There were all styles and colors. I picked through the piles of panties and found some I though were cute. A few women walked by slowly. I could feel them staring at me as I searched through the piles of satin, nylon and lace. But I didn't look at them,
I wasn't going to let my nervousness stop me from get my things. I was going to buy my lingerie, no matter who was looking.
Next I walked over to the teddies. They were cute, but I would have to unsnap the crouch for access to my bum. I decided to buy a teddy at a later date, after I bought all my necessities. I found the girdle and garter section. I liked garter belts. Garters are so sexy. Plus with the girdle, I would have to take it off to have my pussy pounded. The whole point of dressing for sex was that I could wear lingerie while being fucked. There were only a few styles and colors, but I managed to find a belt that was a close match to a pair of panties I had picked. They were pink with white lace.
I figured I still had enough money for some other things. I wasn't buying the best stuff, more like the bargain items. I would get better things as I saved up. I headed to the bras. As I searched through the displays, a saleslady came over to me and asked if she could help. I was nervous and told her that I was fine then thanked her. She started to walk away when I decided I needed to get her opinion on sizes. I asked her if she could help me size a bra. I had not checked mom's bras for the size she wore before I left. The saleslady asked for whom it was for so that she might have an idea what the shape might be. She had a pleasant smile and a calming voice. Her nametag read Debby. I was going to tell her that I was be hazed by teammates to dress in girls undies. But I went with the truth. I told her that it was for me. She smiled and without hesitation said that a 38C would probably fit me. I think she knew they were for me before I said so. Debby started to show me different bras. I told her I want to match the pink panties and garter. She walked to another display and pulled out an almost perfect match out. I told her that was the one I would take.
Debby asked if there was anything else. After I did a quick addition of the things I had picked, I figured I had about fifteen dollars left over. I asked her if she had any tap pant and camisole sets. She led me to the back wall where she showed me a nice selection. I quickly found a set in pink, a bit brighter then my other pinks, but that was ok. Debby suggested an extra large size. I was set now. I had everything I wanted. I told Debby I was done for now.
Debby took my things and we headed to the register. After paying, I thanked her for her help. Debby said that she would be glad to help me if I came back. I told her that I would look for her next time. After leaving the store, I began to check out some of the ladies clothing stores window displays as I walked through the mall. I had about twenty minutes before I was to be at the car.
I needed to hit the men's room before I left, so I headed in. As I entered I noticed that it was empty. I went to the stall against the wall and locked the
door. I dropped my pants and underwear and sat down. During a long pee, I reached into my bag and pulled out the pink panties. I thought that if I was quick and quiet I could put them on now and wear them during the ride home. Then I got crazy and pulled out the garter and black stockings. I would try to get into them all. After pulling my jeans and underwear off and hanging them on the door hook, I yanked off my socks. Then someone came in to pee. I quietly slipped my shoes on and waited until he finished. He zipped, did a quick hand wash and left. I took my shoes off again and began to work the nylons on. I got each up to my knees then put my socks and shoes back on. From out side the stall it would look like I was wearing shorts. Next I stood up to attach the garter belt, then each of the stockings. My hands were shaking from the thrill of dressing in sissy things while in a men's room at the mall. I wiggled my bum feeling the straps tickle me as I pulled my stockings up. With my tall size stockings, the straps didn't seem to be pulling as hard as with mom's shorter stockings, but they still felt very sexy. I was about to pull on my panties when I heard someone come in and close the door two stalls down. He dropped his pants and let out a grunt, and splashed into the bowl. He started to rustle a newspaper, which allowed me to continue. I quickly pulled up my panties, tucked my stiff girly cock in then took off my shoes again and slowly put on my pants, careful not to snag my new panties when I zipped up. I stepped into my shoes once more then put my jockeys into the bag and flushed.
I opened the door and went to the sink to wash. In the mirror I checked to see if everything I had on underneath looked ok. Satisfied that nothing was showing, I grabbed my bag and started for the car.
As I walked I could feel the nylons and panties caress me under my jeans. This was the first time that I wore undies under my male clothes. The garter straps brushing against my thighs felt great. I took my time walking out to the car.
Rob and Mike were in the car waiting. I got in the back seat. After closing the door, Rob looked in the rearview mirror and asked "did you get what you were looking for?" I smiled at the mirror and said I did and more. I could see his eyes brighten.
It was dusk as we drove back home. Mike asked Rob to drop him off at his house. When we got to Mike's, he and Rob discussed plans for later that night before Mike got out. I moved to the front seat after Mike left. As we drove away, Rob asked me to show him what I had bought.
First I showed Rob mom's replacement nylons. He nodded his approval. Next I pulled the remaining three pairs of panties and dangled them near his face. He was trying to look at them while driving. He said "they look cute". I
put them back in the bag as he asked what else I had in there. I told him that he couldn't see them. When I put my things on in the men's room, I had no plans for Rob to see me tonight. When I put them on, it was for my thrills only. But I started to think that I'll tease him by showing him what I was wearing. He'll be horny thinking of the things I was dressed in until we "get together" again. "Getting together" meant him fucking me while I am dressed in lingerie.
I told him that he'll just have to wait for another time. Rob kept asking, like a kid who couldn't wait for his birthday present. I knew he would. After a couple more "show me" demands from Rob, I grabbed my belt buckle and undid it. Unsnapped my jeans and pulled the zipped down. Rob was having a hard time watching the road. His head was on a swivel trying to watch what I was doing. He swerved a couple times so I told him to watch the road and I'll tell him when to look over to see. Rob turned looking straight forward as I lifted my hips to slid my jeans down. Once my pants were at my ankles, I told Rob he could look. In the low light of the evening he could barely see my things, so he turned on the overhead light. He saw everything now. His eyes lit up, as he said "verrry nice". Rob reached for my stocking covered thigh. I told him to keep his eyes on the road, that I didn't want to be found in my sissy undies if he wrecked. Rob drove with his left hand on the wheel and his right hand on me. I scooted over on the bench seat, to get nearer to him for both our conveniences. Rob caressed my thigh at the stocking top. He stuck his fingers between my legs and tickled me.
My sissy cock was stirring under my fresh new panties. It started to form a tent as I reached to turn the light off. Rob moved his hand up to my sissy cock and stroked it. I tilted my head back and enjoyed his touch.
Rob teased me for a while, until I decided to return the favor. This was going farther then I could have planned. I reached toward his zipper and pulled it down so I could get a hand in. Rob told me to undo his belt and jean button. After getting the belt and pants open, Rob lifted his hips off the seat. I tried to get his jeans and underwear down but we came to an intersection. Rob had to sit to use the brake pedal. After we got through, I slid his pants down to his thighs. I stroked his warm hard cock as he drove on. Our arms were crossed as each of our hands groped the others cock and balls. Mine covered with my pink panties, his naked to the world.
I wasn't paying attention to where we were going, but it seemed to be taking longer then usual to get back home. I looked out the window and saw fields. We were not going home I though. We were going out of town. I asked Rob where we were going. He said that he knew a place where he takes girls parking. I got excited knowing what Rob had in mind.
I kept playing with his cock as we pulled into a dirt road. We drove a short
distance before Rob turned off the headlights. We slowly drove up next to a group of trees just off the road. Rob told me to get out. I had to get my pants and underwear off before I could step out. I put my shoes back on and got out. We quietly closed the doors and Rob walked to the front of the car. He was holding his jeans up with one hand. I was standing outside in my panties and stockings with the feel of a cool breeze passing through my legs. I was getting a chill from the evening air and my excitement. Walking towards Rob, he let go of his pants. They dropped to his ankles leaving his hard cock bobbing in the early evening moonlight. I leaned down and gave its head a kiss and a lick. Rob put a hand on the back of my head, forcing me to take more of his length. I didn't need to be forced I was willing to suck him. He then grabbed my shoulders and tried to push me down on to my knees. I resisted that, I wasn't going to ruin these nylons too. I pulled off his cock and told him that I wouldn't kneel in the dirt in my stockings. Rob kicked off his jeans, hopped on the fender of his car and spread his legs open.
I walked up to Rob, put a hand on each thigh and pushed my nylon covered cock up against his balls. I stood on my toes as my sissy cock slid under his balls and up along his shaft. We kept our faces back away from each other. We've never kissed on the mouth and we had no urge to do so. Ours was strictly a sexual thing, not emotional.
A few more up and down rubs with my slick panty covered cock head and I was ready for more. I pulled back with my hands still on his legs, bent down, and kissed Rob's sack. I flicked my tongue over his cock head, licking the precum off its hole. My warm saliva in the cool air formed wisps of fine steam rising from its head. I began to finger his ball sack but noticed that it wasn't soft and bouncy as in the past. It had tightened from the evening air. I then completely swallowed Rob's stiff pole to his pubs. I worked my mouth down his shaft like I was hungry for cock, and I was. Here I was, standing outside in my stockings and panties, leaning on to a car, sucking a hard cock. I was horny as hell. In the dark of the night, I felt like a girl on her first date. I knew now what it was like for a girl to be parking with a guy and have her face buried in his crotch. I was more willing to go all the way than most girls would. Unlike girls, I had no fears of getting pregnant. I was expecting to go all the way now. I would have been crushed if we didn't fuck tonight. As I bobbed on Rob's shaft I thought how quickly my plans for tonight had changed. I was planning to go back home, wearing my panties and watch tv. But now I was going to get my bum filled with gooey cum.
After what seemed to me to be a short period of time, Rob said to stop. He grabbed my head to keep me from going down on his pole. I tried to continue but Rob slid off the car. I kept my mouth locked on his cock, but had to let it go. As I stood up straight I saw Rob, naked from the waist down,
walk to the back of the car and opened the trunk. I couldn't see what he was doing until he closed the lid and headed toward me. He had a blanket in his hand. No doubt he had fucked girls on it when he brought them out here. I waited to see where he would spread it out. I figured he would lay it under a tree.
Instead of laying it on the ground, Rob laid it on the car fender and hood. After smoothing it out he told me to lean over on to the blanket. The fender was flat, perfect for being bent over on. I stepped to the car with a smile knowing I was going to enjoy this. I was still wearing my male shirt, but everything from the waist down was female. As I leaned down on to the hood, it was still warm from the engine inside. I teasingly grabbed Rob's cock as he stood beside my hips. I released it as I laid flat on my tummy waiting for his next move.
My nylon covered bum was sticking out waiting for Rob's attention. He stepped behind me and placed his hands on my hips. He leaned into me poking his cock into the crack of my pantied ass. He told me to spread my legs wider apart. I adjusted my feet, allowing him easier access to my butt. He stepped closer, his cock head up against my ball sack. His hands began to rub and caress my cheeks, sending shivers up my spine. Goose bumps rise up on my thighs and bum. Rob ran his hands down and around the front of my hips, between my bare thighs, down to the tops of my stockings. Rob kept his cock tucked up under my ass, against my balls. I was in heaven. He leaned back to allow his cock to spring up and press between my cheeks. He worked his shaft over my nylon covered hole. Teasing my pussy by poking its head into my entrance. When I couldn't take anymore, Rob patted my cheek, stepped back and walked to the driver's door. He leaned in through the window, fumbled for something, than came back over to my wanting ass. I turned my head, watching what he was doing. I saw a tube of some kind of gel in his hand.
Rob hooked a finger on to a leg band of my panties and pulled to one side exposing my rose bud to him. I could feel the cool of the evening air rush over my pussy hole. I felt tighter then ever now. Rob reached under to free my balls and cock. My girly cock was forced up against the blanketed fender. My whole four and a half inches was trapped against the car. I had little chance of impressing the girls with my sissy cock. Maybe my future was with the boys I thought. I reached one hand back to my bum and took the silky material from Rob's hand. I pulled as far as the panties would stretch. I knew he would need both hands for what was coming.
Letting go of my panties, Rob opened the tube of gel. Squeezed some into his hand, then place the tube beside my hips. He rubbed his hands together spreading and warning the gel. Instead of smearing my ass hole with the
gel, he reached between my legs. Rob wrapped my cock with his slick fingers, rubbing up and down its stubby length. I had to catch my breath. I had not expected him to do that. I loved what he was doing but I wanted my ass packed. I wiggled my hips and told him that I was fine. It was nice of him to give my cock attention, but what I really wanted was for him to fill my asshole now.
The juice in my balls were boiling up but I could take care of that later myself. I wanted to get to the fucking. The building anticipation was driving me crazy. Rob stopped his fingering of my cock and balls then squeezed more gel in his hand. Warming the gel in his hand again, he placed his gooey covered palm against my hole, wiping most of the gel into my pussy entrance. His left hand moved to the small of my back. He grabbed the garter belt and waistband of my panties together. Rob pulled on them like the reins of a horse, using them to control me, to keep me from moving away. He should have had no concerns for that, I was anxious for him to start fucking me.
The first finger of his right hand began to probe around my butt crack, trying to find my rose bud in the dark. When he located my hole, he wiggled the tip in an inch or so. I waited for the pain to hit. With so much lube, it wasn't too bad. Being the fourth time that Rob had invaded my tender pussy with his fingers, I was relaxing easier. I knew what to expect. His opening of my pussy was becoming familiar. I did need to be stretched to accept his six inches of boy bone. With more pressure, his finger slipped through with little resistance. He held it in a few seconds then pulled out. With his left hand holding me steady, he added a second finger to my opening. Both gooey digits slid in with no pain. I was feeling pretty good at this point. I thought his last two fingers should present me with little trouble. Rob added the third finger at my opening. Instead of him pushing them forward, I pushed back sinking them deep inside. This time a twinge of pain ran through my hole. It quickly passed and I ground my pussy into his hand. I slid forward on the hood as Rob worked his fingers in and out until I was quite loose. Rob placed all four fingers in my pussy, I swallowed them with ease. Rob asked if I was ok. I let out a low moan of "ummm hummm" into my free hand that my face was resting on. I wiggled my bum letting Rob know that I was fine. Rob twisted his hand around in my pussy. I could feel him tickling my innards. I squirmed my ass in satisfaction. I wanted his male meat in me. I told him that I was ready. He pulled his fingers out and patted my bum tenderly. I felt a brush of cool air at my entrance when his hand was removed, sending a shiver up my back.
I could hear Rob greasing his cock in preparation for reaming my ass. He smeared more gel at my hole. Rob's left hand was still holding onto my sissy undies. His grip was firm but not forceful. I was still holding my
panties off to the side, at least until his cock entered my pussy.
Rob wiped his gooey right hand on my panties, then placed his cock head against my slick pussy hole. Holding his boy bone steady until his head would pass through. His hips snug up against my bum cheeks. His thighs wedged inside mine. Rob was ready and so was I. He rotated his hips forward pressing the tip into my hole. It slipped off to one side because of the slick gel and my pussy tightening a bit. I groaned my disappointment. His free hand aligned his head and held it straight while he pushed again. He met little resistance as his head popped into my opening. I had no pain so I slid back while the head tunneled inward. Rob pulled me farther back with his left hand. He was deep inside, his balls touching mine. I let go of my panties, bringing that hand also up under my mouth. I let out a soft throaty moan as I ground my cheeks against Rob's hips. I wanted to get every inch deep inside. The fullness I felt from Rob's cock almost caused me to pass out.
Rob slid me forward on the hood, as his head popped out. It bobbed around at my entrance. Teasing me, taunting me. I was ready to cry. I decided I wasn't going to let him torture me, so I pushed back impaling myself on his cock. I caught him by surprise, he didn't expect it and didn't have time to stop me. I told him "quit screwing around and start fucking me or I'll get in the car". He knew I didn't plan to stop now. Right then, Rob could do what ever he wanted, but I would be ticked if he didn't start poking me.
Rob leaned into me, I slid across the fender again. He placed his free hand on my bare hip and held me tight. It felt like he was deeper then ever before. It was probably the perfect ass fucking position, allowing the deepest penetration. Either that or his cock grew a little longer. For whatever the reason, I was enjoying our best fuck yet.
Now Rob was going to take control. Holding me at my hip and by my undies, he pulled three quarters of his length out then back in. He started a smooth slow steady sawing motion in and out of my pussy ass. I lad there submissively like a girl, just loving the sensations. His warm smooth shaft gliding on the gel, bumping his mushroom head against my walls. I slid a little from the blanket sliding over Rob's freshly waxed car hood, but he didn't let me move much. He was controlling us both. Rob pumped me like I was a sex toy. He didn't care if I wanted it fast or slow, he was doing what felt good to him. After a few minutes of his steady motion, he began a slight increase in his speed. My pussy hole was growing warm from the friction of Rob's cock. His force was also increasing with his speed. He held me while he bucked in and out. Not moving except at his waist. His hips barely left
my thighs. He seemed like he could go all night, but I couldn't. I want him to start ramming me hard and fast. I wanted him to shoot his load now.
His hips rotated around, the head of his cock tapping my innards. I stood on my toes, trying to make the feelings even greater. Rob slid in and held still, he moved his feet backward slightly. This gave him better leverage into my ass. He pulled partway out then in a little harder. Rob picked up his fucking speed times two. I knew we were getting close now. He began to pound me for his own pleasure. He didn't care what I wanted. I was just along for the ride now. My pussy was loosely holding on to his shaft. He was opening me up wider as his force increased. He began to push and pull me to meet his motions. I was being yanked around like a doll.
Rob's pace quickened to the point that I couldn't keep up with him. He held me firm and slammed my pussy like a dog on a bitch. He was banging me harder than at any time before. As he fucked me with little mercy, I hoped for this to end. I wanted his cum now. But Rob didn't care what I wanted. He fucked me harder and faster. His cock swelled as he grunted and groaned. I held my breath and waited for his shots to start. He felt like he was going to explode, and he did. Rob let lose some powerful jets of cum into my love canal. He kept slamming me as his cock shot blasts of his warm juice in my hungry ass. My pussy sucked out his goo as fast as he could shoot it. We were both now moving back and forth, milking as much cum as we could get out of his balls.
As Rob's squirts of cum weaken in force. He kept fucking as if he wanted more. I had enough, but it seemed like Rob want a second go at me. His cock wasn't shrinking much, staying hard, he got back into a steady rhythm as if he hadn't shot a load yet. I began to get into it again. I guess I got my second wind. We were trying to adjust our motions to get in sinc with each other. After a couple tries, we got going again. This time Rob was letting me do more of the action. I was sliding across the hood, pushing my ass to meet Rob's boner. His shaft slid with ease through the mix of gel and his thick cum. We just couldn't get enough of this tonight. His cock felt like it belonged inside of me.
As we pounded into each other, we heard a rustling noise behind us. We stopped and held quiet for a second or two, waiting to hear more noises. That ruined the moment. Rob said he was pulling out and I was ok with that. We may have had a second shot at him cumming if it hadn't been for the noise. I guess we were both a little more nervous about being out there now that Rob got his first load off. The noises may have been around us earlier, but we heard nothing as we fucked like animals. Since Rob got off once we would call it a night.
Rob pulled his semi hard cock out letting my panties slid back across my leaking pussy. He grabbed the elastic band and pulled it across snug, covering both cheeks. Rob's warm goo ran down to my sack and dripped into my panty crotch. As he wiped his cock off with the end of the blanket he told me "get in the car, we're leaving". I told him I would leak in my jeans and on the seat. He tossed me the blanket and said I could set on it, but we were leaving now. He said he had to meet Mike in a little while and wanted to get cleaned up. He pulled on his underwear and pants as I walked around the car. The idea of sitting in cum all the way home was not appealing to me. I loved cum, but not in my jeans. Rob got in and helped me lay out the blanket on the seat. I sat down and reached for my pants. Rob started up the car and began to back out. My door was still open. I told him to stop so I could get dressed. He told me to put them on while we headed home. I closed the door and started to remove my shoes. Now I knew how some girls felt after they put out on a date. "Wam bam, thank you mam"
As I sat in my cum soaked panties and jeans riding home, I said nothing to Rob. He said nothing. He reached over and turned on the radio. It's always awkward when we finished our affairs. Not knowing what to say. I didn't want to sound like a fag, trying to find out what Rob was feeling. I guess I was fine with us fucking then going our separate ways. I didn't want a relationship with Rob, but I couldn't even start a simple conversation with him. So I sat quietly figuring out how I was going to get to my room with the stain in my jeans.
As we pulled into the driveway I thought I would jack-off later, maybe before I put my sissy things away in my closet. I would wash out the pair of panties I was fucked in tonight after the parents went to bed.
When Rob stopped the car he told me "wash the blanket and put it in my bed room". I sat gathering up my things as he got out. He stopped, turned around before closing the door, leaned his head in and said "it was nice tonight. Don't get weird about it. If you're ok with it, we'll keep doing it until we're ready to move on. Its not like we'll be doing this our whole lives. Its just for the sex". I smiled weakly and nodded.
We did it a few more times. I'll write about the next time soon.