I've had a thing for vans since my teens. Even in my forties and now into my early fifties, I've own a van. I fucked my wife in a van the night we met during a van club party. This fondness for vans started back in the late sixties. Back then a teenager with a van was cool. My brother Rob bought a used van to drive while at college. He figured that it would be good to take his belongings to and from school and help get him laid. It did help him get laid even before he got to college. We fucked in the van while at a drive-in theater.
Getting dressed in lingerie and having my brother fucked my ass was just heavenly, I did wished the opportunities were more frequent. During a late night trip to Rob's room to chew on his a boy bone, the idea came to me to use his van for an affair. After I had swallowed his warm gooey load, Rob said that he needed to fuck someone. His girl would be away for a month with her family on vacation. I took the hint.
I said "if you want to go parking, I up for it."
Rob said the last time he girlfriend went to their parking spot, other people had found the place. A couple cars drove past them as they made out along the dirt road. He didn't feel comfortable going there any longer, especially with me.
I thought a few seconds and blurted out "how about a drive-in in the van?" I thought what a better place to make out at. Besides, anyone who saw us would think that I was a girl from a distant with my shoulder length hair.
Rob laid quiet for a moment then said "that's not a bad idea. We could go to one out of town. Chances are no one we know will be there."
Being it was mid-week we planned to wait until the weekend to go. On Thursday evening Rob found a Clint Eastwood movie "A fist full of dollars" in the newspaper, that was showing at a drive-in about fifteen miles away. We agreed that it would work
Saturday finally came. I was horny as hell. Before I left for work in the morning, Rob told me to be ready when he got back from his job at the local department store, around seven. After getting back from work at six-thirty, I took a shower, than headed to my room to dress. I dug out my boxes of sissy things, and selected the items I would be wearing. I was going to wear my lavender outfit. A bra, garter belt, black stockings and panties. I also picked a pair of white satin panties for Rob. He didn't know it yet, but I planned for him to be wearing panties tonight also. Before I began to dress, I checked to see where my parents and younger brother were. I didn't need anyone walking in on me as I putting on my girly undies.
First came the bra. I reached thru the arm straps and hooked the bra behind. I quickly put my male shirt on over it. Next I stretched the garter belt around my waist and attached the two hooks. I was getting pretty good at hooking stuff behind me now, then the panties. I stepped into the leg holes and slid them up over my sissy hard-on. I pulled the stocking claps thru the leg openings. Sitting down on the bed, I carefully worked the stockings on up to my knees. I stood up and stepped into my jeans. If anyone came in, I could yank the jeans up and cover my undies. Gently pulling the tops of the stocking up my thighs, I connected each to the straps. There was that tug of the stockings that made me feel so sexy that I wanted to prance around wearing only them. I love garter belts and stockings the most. The way they frame my cock, balls and ass it's so sexy. I
I reached for a pair of socks to put on to cover the nylons that would show above my shoes. Suddenly my door opened. I panicked, dropping the socks and started to pull up my pants. With the jeans half way up my legs, Rob poked his head in the door.
Rob said "Good, I was hoping I would catch you getting dressed."
I said, "You bastard, I thought you were mom or dad. You scared the shit out of me."
He laughed and said, "Sorry, I wanted to make sure you had on your lingerie tonight. I asked him if he approved. Rob said, "It's perfect. See you in the van in about a half hour."
Rob had little to be concerned about. Wearing women's lingerie was my true motivation for letting him pound my bum. If I were not wearing my panties, garter belt and stochings, I don't think I would have been as willing a partner.
After Rob left, I finished dressing, filled my bra cups with white nylons, then stuffed Rob's panties in my pocket. I headed to his room to catch him before he took a shower. As I stepped into Rob's room, he was gathering his clothes. I closed the door. He asked me what I needed. I pulled out the panties and tossed them to him.
He caught them then asked, "What are they for?"
I told him "wear them tonight."
He said " What? Hell no. I'm not the one who's into girls underwear."
I said, "If you don't, we may as well not go, because we're not fucking unless you're wearing them."
"What the hell is this about?" Rob demanded.
I said "Just please put them on this once."
This was the first time that I had put any conditions to Rob of our affairs. Rob sensing I really wanted this and the fearing not getting laid tonight, he thought for a few seconds then said, "Alright, you bitch. I'll wear them this once. You've blackmailed me in to it. But I'm not doing this again. And don't try any weird shit tonight, like trying to fuck me."
I smiled saying, "Thanks, I hadn't thought of that. That's a good idea. We both would be virgins at that." He gave me a stare of discuss as I turned and left his room. Little did Rob know, that's exactly what I was planning to do.
While Rob showered and dressed, I grabbed some pillows, blankets and a towel then went out to put them in the van. I figured some cushioning on the floor of his van would be needed. He had laid some carpeting on the floor but it would still be hard on the knees and ass without more padding. Rob also had two large beanbags in the back. With only the two captains chairs up front, he had them for whoever else needed a seat. After I stretched out the blankets and tossed the pillows around, I got in the passenger seat and waited.
About ten minutes later Rob came out of the house with a blanket and a couple pillows in his arms. I chuckled as he opened the side door and saw what I had already done in the van.
He tossed his things in saying, "Looks soft enough to fuck on."
I said "If you're dressed for it."
Rob snapped back "Don't worry, I'm wearing them." Then he went around and climbed in the driver seat.
I looked straight ahead and said "Don't they feel great against your cock?"
He said, "I'm as hard as a lead pipe. You'll pay for this. I'll fuck you raw tonight." I snickered as he backed out the driveway.
I tried not to sound like a fag as we tossed sexual insults and jabs back and forth during our ride to the drive-in. I was so excited I couldn't wait to get stripped down to my panties. As we got close, Rob said that we would wait until the movie had played a couple minutes. The sun would still be setting when as the previews played and the movie began. When Rob pulled up to the ticket booth to pay, I slouched down a bit. I avoided looking at the guy selling tickets. After paying, Rob drove along the back row and parked at the far end. Before he placed the speaker in the window, Rob asked if I would get something from the snack bar.
I said, "If anyone sees me, they'll know that there's two guys in the van."
We were trying to avoid that, because when the windows fog up later, people would figure out what was going on. He agreed that I would stay in the van and he would go.
When Rob got back with the popcorn and drinks, he said he saw a couple cute girls at the snack bar. They were wearing halter tops and hot pants. I asked him why he didn't ask them back to the van.
He said, "I was, but if they didn't put out, we would both be going home hornier than we already are. Besides I know I'm going to get some, so why take a chance and lose that opportunity."
I smiled a shitty smile and said, "That's true."
A few minutes later they began showing the previews and advertisements. The sky behind the screen was pink as the sunlight disappeared. I was so horny from the anticipation that I reached over to Rob's crotch before it was completely dark. I made small circles over his hard cock pressing against his zipper. He then reached and fondled me through my shorts. I stopped teasing him and undid my jean button. Then Rob helped pull the zipper down. I was relieved to finally have my cock freed of its confines. My little sissy cock was poking up just past my opened pants. Rob slipped his hand in and stroked my lavender wrapped shaft. I lift my hips up and pushed the jeans down over my thighs to my knees. I kicked off my shoes and leaned forward to push the jeans off my feet. Rob was forced to remove his hand while I worked my pants off. Now I was sitting in my garter belt, stockings and panties feeling very naughty.
As he reached again for my little dickie, I told him, "Take off your cut-offs." I wanted to see that he did put on the panties.
He asked with a grin, " Don't believe me?"
I said, "Drop 'em."
Rob undid his belt and snap. I pulled on the zipper as he spread his shorts open. With his zipper open, my fingers slithered in. I let out an "aaaaah" when I touched his satin wrapped shaft. I slip my fingertips up to its head and teased it until Rob rose up and took his shorts off. Rob nervously looked around the van to see if anyone was near by.
I said, "Relax, no one cares what we're doing."
We sat back in our panties and watched the movie begin. Our arms crossed as we caressed each other's boy bone thru the satin material. Rob said that he was still not comfortable. He felt exposed.
I said, "Well, go to the back and sit."
Rob nodded a yes, turned the captains chair around, slide out and onto his knees. My hand didn't leave his crotch until he crawled away.
The windows at the side and rear doors were covered with curtains. Rob had put them up after getting the van. There was soft light that shown through the curtains. It was just enough to see as we moved around. Rob moved the bag so he could see the screen then sat in it. I turned my chair to face him. Stretching out my legs, I placed a foot on either side of Rob's hard boner. I could rub his shaft with my stocking covered feet. I teased him with my toes for a few minutes until I couldn't stand it any longer. I slid out of my chair and crawled towards him.
Rob said, "I don't like the front window not being covered. I feel exposed."
I grabbed a blanket and looked for a place to hang it from. I didn't find any place to attached it so I threw it over the chair backs. It covered the lower part of the windows from view. I looked back to Rob and asked him if that was ok.
He said, "That's better."
I crawled to the back and sat between Rob's legs facing him. As I lifted up his legs to my shoulders, he asked me what was I trying to do. I told him to relax and enjoy himself. I crawled on my knees until my sissy cock was laying down against his stiff shaft. Two layers of satin separated our cocks. I leaned against his legs and began to dry hump his dick. Our cocks twitched and squirmed as mine glided smoothly along his. I worked my head into his sack and the sensitive spot behind, just in front of his bum hole. Rob moaned as I poked and rubbed until I was ready to shoot my load.
Rob pushed me away with his legs saying, "That's enough, or I'll blow any second. Then neither of us will get what we came for."
I reluctantly agree then backed up and crawled to the other bag. I pulled the other beanbag over beside Rob. Took off my shirt, exposing my bra. I was now ready for our night at the movies. I helped Rob take off his shirt and he settled back. The bag cradled Rob's backside, his legs bent up slightly. I reached between them and rubbed his cock and balls thru the satin. Rob let out a low "ummm" as he rolled his head back. I leaned over, my mouth above his tummy. Then I began licking the top edge of his panties. As I blew my warm breath down over his cock head, Rob reached behind his bag and brought out a bottle. He twisted off the cap and told me to hold out my hands. It was perfume.
Rob said, "This will make you smell like a girl."
I wasn't insulted. I thought it was a great idea. What a better way to feel more feminine? I cupped my hands as Rob poured a generous amount out. Most of it I caught, but some leaked onto my thigh. After he stopped, with my hands held together, I drizzled some onto my tummy. It ran down to my garter belt and pooled in my belly button. I cupped the remaining perfume in one hand and dabbed my other hand in. With my damp fingers, I reached behind to my bum and rubbed across my cheeks under the panties. The last small amount remaining was rubbed between my palms. I patted my hands onto the front of Rob's panties. The stale van air was now filled with the sweet smell of a woman. I felt so sexy that I buried my face into his crotch. I kissed and nibbled on Rob's shaft like a nympho. After a few minutes rubbing my face along Rob's length, I reached in to his panties and pulled his cock out. I devoured him in one quick motion. I was moaning from the pleasure I felt with Rob's lovely hard cock in my mouth. Rob tapped my waist to indicate for me to swing my hips around towards him. I did a pivot while still holding his boy bone between my lips. Now I was at a slight angle with my head down, buried between his arched legs. My ass was near his shoulders. Rob reached between my legs and up to my sissy cock. As his fingertips tickling my balls, my girly cock twitched inside their satin wrap.
During most of our affairs, Rob was willing the lick me while I sucked on his pole. Not quite a sixty-nine, but close. So I hoped he would do some oral teasing tonight. I raised my leg up over his head and straddled his face. Rob slid my panty crotch to one side, releasing my four and a half cockett and sack.
I wanted to suck the salty cum from his balls. I was so horny I didn't want anything to stop me. But Rob did.
He told me "slow down, we've got plenty of time."
I mumbled "Not long enough."
I would've loved to swallow a load now, then take a load in my ass pussy. But the movie wasn't going to last that long. I figured I better ease up before he shot his one load of the night. I wanted my bum filled more then my stomach. I began to lick his head and balls as I caught my breath. Rob flicked his tongue around my cock teasingly.
Rob shifted in the bag reaching beside it. Pulling out his jar of gel and opened it. Once his fingers were coated he smeared my rose bud and began to poke inside. I rested my face against his rod as I waited for the burning to pass. His first finger entered easily so he added the second. I loved him diddling at my pussy hole. I was going to do it to him. I knew he said, not to try anything weird, but I wanted to see what he would do or say. I dipped my hand in the gel, then over to his bum. I carefully exposed his entrance while he was distracted with stretching me open. I gently placed a gooey finger at his hole. With light pressure, pushed the tip in.
He buck and asked, "What the fuck are you doing."
I said, "Lay there, shout up and relax. Just keep doing what you were doing."
I wanted to do this whether he liked it or not. I think he was curious about how it felt but didn't want to sound like a fag asking for it. So I eased my finger in an inch at a time. When I felt resistance, I would stop then wait a few seconds. His hips moved about and he grunted a bit but didn't protest again. I asked him how he was doing.
Thru his panting, he said, "It takes getting use to."
Rob had laid back with his two fingers still in my pussy, concentrating on my finger at his virgin hole.
When I got the first one in completely, I said, "If you don't keep stretching me, I'll have you ready first."
He snapped out of his trance and pushed the third finger in with little finesse. I was pushed forward from his force. I slipped my finger out and added another. He was taking it better then I had expected. A couple grunts, but he didn't resist. Rob had all four fingers inside me before I had started on my third. I needed to get him to take at least three fingers to accommodate my girly cockett. So as my third finger disappeared in his bum, I now had to somehow get him to allow me to fuck him. I wasn't sure if he was going to go along with that. Holding my hand in his bum, I gave his cock some attention. Kissing and licking along its length, trying to get him in the mood to accept my next move.
Without warning, I rolled off to one side. As I twisted away, Rob kept his fingers in me. I Crawled away from his hand, still with mine in his ass hole.
He asked, "Are you ready?"
I said, "Yes, roll over."
Rob said, "What do you mean, me roll over?"
I said, "I want to fuck your ass."
He protested, but I told him, "Come on, I'll be gentle, besides you'll probably like it once you've try it." Like I said, I think he was willing, but he didn't want to give in too easily. After some more half-hearted complaining, Rob got up.
As he started to turn over in the bag, he said, "Just this one time and don't breath a word to anyone."
I said, "Oh yea, like I'm going to go around telling people that I screwed my brother. We're in this together, so to speak."
I told him to shape the bag so he could drape himself over it. As he leaned over the edge, I wiped some gel all over my cock. I couldn't wait to fuck him. I crawled up behind his bum and stretched his panties to one side. He wanted to take them off but I talked him into keeping them on. I caressed his satiny cheeks as my nob touched his puckered hole. I had a glob of gel at the tip to help grease the way in as I pushed. I asked him if he was ready. Rob let out a mumbled, yes. Placing one hand on his satin covered hip, I took a deep breath. I put the other hand on my shaft to keep it straight, then leaned into him.
I was shaking from the anticipation, my first fuck. I almost hyperventilated. As I pressed into his warm slick bum, I tried to calm down. I felt him resist as the head pushed thru. I held still allowing him to adjust. I wasn't big at all. It wouldn't hurt too much as I slipped thru. Rob slid forward across the beanbag as I pushed in again. His "O" muscle at the entrance was tight around my shaft. I was about to ask him if I should continue.
Before I could, he whispered, "Keep going, I'm ok."
I pushed my hips forward, burying my sissy cock to its base. My stockings were rubbing against his cheeks. I couldn't believe it, my dick was completely inside. My cock twitched as I held tight onto his hips. Rob let out a gasp. He was taking it better than I could have hoped.
Rob whispered, "Get started before I change my mind."
I figured I was now in control and wanted to drive him crazy like he did to me. But I just couldn't wait any longer. I pulled out, than slid back in. I could tell that I wasn't going to last very long. I was so excited about finally fucking, that my senses were over loading. I rotated my hips in and out a couple times then felt my boy juice boiling up in my sack. I wanted this to last a few more strokes, so I stopped and fought the urge to release my load. I was able to hold it off, but not for long. I told Rob to get ready, I was going to shoot soon.
He mumbled, "Fuck me! Just fucking shoot. I can't take anymore."
I took that as he was ready too. I had to be careful not to pull back too far or I would pop out, that would have driven us both nuts. I started to slide in and out quicker. My pace was at three quarter speed. It was a wonderful feeling. My cock was on fire. My leg and stomach muscles burned from this new type of workout. I wanted to fuck all night. But sooner then I had hoped, I lost control. My hot cum shot up from my balls, thru my cock, splashing into Rob's bum. It was a very sexy feeling, to blow my load inside of someone. To shoot deep into a warm wet place. Rob would suck me but never kept me in his mouth to cum. It was always out in the open when I released. This was like nothing I had felt before. I continued to bounce my thighs off his cheeks a few more times. Milking out as much of my juice as I could. Rob laid groaning and sweating.
I slumped over on to his back. Spent from the new experience. I hadn't ever done that much work while being fucked. At that point, I wasn't sure which I liked better. Fucking someone and doing all the work, or being fucked and let someone else wear themselves out.
He laid still as I planted soft kisses on his neck and shoulders. Sensing a gay moment, he said for me to get off. My dickie had slipped out before I moved. I rose up and pulled back. My cockett shrank like a turtle into its shell. I rose up and moved back away from Rob's leaking bum. Grabbing a towel, I wiped off the goo that ran down the crack of his ass. I mopped Rob's tender hole until he rolled over and took the towel from me.
As he cleaned himself, he said, "Grease up, cause you're going to pay for that."
I asked him, "How'd it feel."
He snapped back, "Ok, but I feel like I have to crap."
I chuckled a bit then scooped some gel in my hand. First I smeared gel on Rob's still hard cock. It seemed strange to me that he was hard. I usually lost my stiffness when I was being fucked. He must have been really horny I thought to stay hard thru that. Either that or he enjoyed being screwed in the ass. When he was good and slick I stuck the remaining gel in my bum hole. I was a little tight but it would be ok.
I wiped off my hand and crawled onto the bag. When I was about to lean on it like Rob had done, he said to lay on my back. I sat down, squirming my bum around to get into a good fucking position. Rob, on his knees, moved in between my legs and raised them up. With one hand, he reached for my panties to pull them off.
I asked him, "What are you doing?"
He said, "Take them off. I don't want them to get in the way."
I did as he said and slipped them down off my hips. Rob had left his panties on though. As I worked mine up one leg and over my foot, he rolled me back into the bag, pushing against my extended stocking legs. My legs were up on his shoulders. Rob couldn't wait for me to take the panties off completely. Here I was again with my panties, hooked on one foot swaying in the air. Rob's cock head bobbed around my hole. It smeared gel all over my balls and ass cheeks. My bum was at the perfect height off the floor. He didn't have to lean over to slip in. He pushed forward, his cock head poked past my sphincter muscle and sank deep inside. I grunted and sighed as his shaft filled me. Rob stated to saw in and out at a steady rhythm. My eyes were closed. I laid back enjoying the cock that was pounding my pussy. While semiconscious, and being thoroughly fucked, I thought how I would sleep well afterwards. He picked up his speed, slamming into my ass pussy. I moaned and whimpered like a girl. I loved to be pounded in my ass. The taboo of two guys having sex was a rush. I would love to fuck a girl, but I knew I also would want to be fucked too.
Rob's strokes were starting to become irregular. He was getting close to releasing his load of goo. I suddenly rolled sideways off the bag. Rob was completely surprised by my move. His hands still held my caves, but his cock was out of my pussy.
He mumbled, "What the fuck are you doing now?"
As I twisted on to my knees, I crawled back on the bag. I said, "I want to finish doggie style.
Rob said nothing as he re-entered my ass. His head would reach farther inside in this position. I hugged the bag as Rob rammed me hard and fast. It would only be a short time before he released his milky cum. I was biting the bag to keep from squealing like a sissy. I was ready for him to fill me.
I pushed back as Rob tensed up. I felt the first blasts of his juice splash inside. I held my ass up to accept all of his hot cream. He was trying to keep fucking but the shots of cum threw off his rhythm. I pushed into him a couple times until I had had enough. After what seemed like minutes, Rob's pulses of cum became weaker and less often. Then they stopped. Rob let out a groan then I felt him shivered while still buried inside me. I smiled to myself thinking of how good it was for me too.
Rob, realizing that the credits were playing on the screen, pulled out and leaned back on his heels. We could hear cars begin to leave the drive-in. I lowered my sore bum and reached for a towel. Rob started to clean himself off. He quickly wiped than began to pull on his cut-offs. After he put on his shirt, He yanked down the blanket and got in the drivers chair. He started the engine and put the speaker back.
Rob turned back to me and said, "You can dress while I drive to the restroom. I gott'a go."
I finished cleaning and pulled my panties back on as he pulled up to the building. Rob hopped out and slammed the door shut. I laid in the beanbag with my eyes closed, trying to regain my strength. A few moments later I heard voices. A couple guys sounded near by.
One guy said in not quite a whisper, "Man, look in the van. There's I chick half naked."
The second guy said, "No way."
The first guy said, "Come see for yourself."
I knew they were at the front window. I laid still but slowly opened my eyes to slits to see who they were. I was nervous and excited at the same time. Silhouettes of two heads were at the front of the van.
The first guy said, "Looks like she's been royally fucked. She's lying in her underwear."
I slowly rolled onto my stomach to give them a view of my ass. I spread my legs open striking a sexy pose.
I heard, "Holy shit, look at that ass. I might just climb in and fuck it myself."
The other guy said, "Not before me."
Seconds later I heard Rob say, "Hey, Jim, Mike how'ya doing."
Jim said, "Rob is this your van?"
He said, "Yea, why?"
Mike said, "Looks like you got lucky tonight."
Rob laughed and said, "More then once."
Both guys let out groans and laughed. I was giggling as I listed to their reaction.
After a little BS and more bragging, Rob said, "Sorry guys, I gott'a get her home. See you guys later."
They said their goodbyes and Rob got in. I asked him, "Were you nervous when you saw the guys outside looking in?"
He said, "Yes, but I also thought you might be giving them a show."
I smiled then sat up and put on my shirt. As he drove out of the drive-in lot and we headed home, I got in front seat and finished dressing. We said little most of the way home. Rob turned the radio on to break the quiet. I was spent and he had to be also. We left the van as it was, a mess, and went in the house. Without saying a word headed for our rooms.
That was our only trip to the drive-in. We had one more affair before Rob left for college. I'll write about it soon.