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Pumped While Wearing His Pumps

Hitching A Ride with the Lothario of Lingerie
What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst.

I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier and was starting to tire of the road. My most recent ride had been with a guy who picked me up in Denver. A hand made “CAL” sign had served me well to this point but by now the sign was so beat up that I no longer could use it. I had been stuck there since about 7:30 that morning and it was now well past noon. For hours it had been just me and…All of the graffiti from hitchers before had been read and reread. “Been here for two days, will probably die here” was one of many etchings on that metallic highway sign post, scratched by a guy with a knife who knew how many torrid summers back. The hot July sun was slowly baking me and I had actually begun to keep an eye to the sky for buzzards that might be circling overhead.

At about 12:45 a car finally stopped. Specifically it was an El Camino wagon looking like something that had been lowered but it turned out be just loaded to the hilt. Inside were a driver with longish black hair and a three day beard and a woman with bleached blonde hair and crooked teeth. The vehicle had Illinois plates. They had one seat up in the back while the other was down flat and covered with boxes. There was no way they could have used the rearview mirror.

“Where are you going?” The guy said once the woman rolled down her window.

“California”, I shouted so as to be heard over the roar of a passing semi-truck.

“You’re in luck we’re going to LA.” My eyes lit up but I waited for the formal invitation. “Go ahead, get in.”

The guy totally looked like an eastern city dude and the woman to his right had nice hair and full, young-looking breasts but an old face housing gentle hazel eyes. Frank Serpico comes to mind. I told him I was actually going to Santa Barbara: “Well, I can take you as far as highway 101 then you’ll have another 100 miles or so to go.”

I thanked him, expressed my gratitude and relief at his stopping, and tried to settle in. He saw me look longingly at a half-buried ice chest. “Help yourself to a cold drink. We got cokes,” he paused thinking for a second, “and if you’re old enough to drink it, some beer.”

I could see him smile in the rearview mirror. I was actually 22 but looked about 18. My face was somewhere between tanned and burned and I was just covered with dust. No telling how old I looked at that point. I would have loved a beer but wasn’t sure that it was good hitchhiking etiquette to drink a guy’s beer until at least we got to know each other. It required some rearranging of stuff to get to the cooler. His cargo appeared to mainly shoe boxes and some flatter, thinner boxes of the shape and size you’d walk out with from Victoria’s Secrets. On closer inspection I saw the words New Exotica on the red box covers. I made like I didn’t notice, opened the cooler, and pulled out a bottle of Coca-Cola.

“Do you folks want anything while I’m in here?” I asked.

He turned to his companion “You ready for a beer, babe?” Since she appeared to be reading a magazine she sort of mumbled in the affirmative. “How about grabbing her a beer. There’s ’a church key stuck to the side of the cooler.”

This was the 1970s before twist off caps were extant. Pop went the bottle cap and I handed the cold, wet brew forward. She didn’t just say thanks; she turned around locked on my eyes and sweetly cooed , “ thank you,” lifting her right eye brow as she said thank. She asked me my name and asked me where I was coming from and they both seemed to take great interest in my tale.

I finally got around to asking them where they were from and what was taking them to California. “We’re from Chicago and we’re on our way to a trade show.” The guy replied. I went on to ask what business he was in wondering if he realized that I had noticed the name on the shoebox.

“I own a store on the north side.” He paused then added. “On Halsted Street.”

Halsted Street? Halsted Street has now become one of the most famous gay ways in the world, although in those days it was just eclectic. I had walked Halsted Street the summer before when I visited Chicago soon after my 21 st birthday and there was a definite weirdness to the neighborhood. Halsted Street and the brand New Exotic sounded like something I might want to learn more about. I was thinking it was interesting that he would mention the street. Something about my visage must have signaled recognition because he then said: “You been to Chicago?”

I related the fact that I had spent the summer of my 21 st year there and that I loved Chi-town. I went on and on about how much fun I had there. I talked about Rush Street, New Town, and Old Town. I said my friend had lived on North Wells Street near Lincoln Park

“Oh, then you know Halsted.” He looked over at the woman and she said something softly that I wasn’t able to understand. From there until well into Arizona we talked about Chicago. I didn’t tell him that I had had some fun at a couple of sex houses a few blocks south on Wells. Or that I had an encounter with a transvestite not far from there, or that I had spent a very hot night in the Chicago YMCA.

As we passed through Winslow, Arizona he announced that they were going to stop in Flagstaff and call it a day. He asked if I had enough money to pay for a hotel room. I said that I did (and in fact I did) and it would be really nice to be able to take a shower and sleep in a bed instead of a car seat like I had two of the three nights I’d been out there. But then as we drove on into the sun it occurred to me that maybe if I had said no I might have been able to share the room with them…or they might dump me at the exit.

They were an interesting pair. His hair was more salt and pepper and his style of dress would best be described as disco chic. He had on the style of shorts that Richard Simmons used to wear on his exercise TV shows and a black muscle shirt. From the legs on down I couldn’t tell. She was wearing denim cut-offs with the frayed threads creating a fringe that showcased her shapely thigh and a tie dyed shirt, more in keeping with the 60s than the 70s but I thought they were stoners, so it was cool. As I handed her the beer I got close enough to pick up the sweet traces of Ciara perfume, one of the great fragrances of the 60s and 70s.

They said their names were Sal and Louise—he called her Weezie with an ersatz urban accent that was actually Southside Chicago. And he treated her sort of like George Jefferson treated his Weezie.

By the time the lofty San Francisco Peaks outside Flagstaff, AZ came into sight we were all in accord that it was time to stop. Sal spotted a Holiday Inn that looked decent. He asked me to walk in with him so I could register and pay for my own room. He asked for adjoining rooms. If I recall it was about $10 for the night. As we were driving around to the back of the property Sal said: “These rooms are probably pretty small so some of the stuff will have to go in your room.” Again this trip pre-dated car alarms so smart travelers always tried to stay on the first floor and empty their cars each night.

“Oh sure, whatever works,” I said anxious to get into a motel room and peel off those dirty dusty jeans.

Weezie went straight into their room while he and I went around to open the gate on the El Camino. He handed me an armful of boxes that I took to his room. They were pretty light and as I walked in the room I asked Weezie what all this was.

“It’s very sexy lingerie, hon.” She said that while standing at the mirror tweaking her blonde tresses.

“You’re kidding,” I said setting the pile of boxes down where she pointed. I looked up incredulously.

“Oh no, open up the box on top.” She had turned to me breasts out, hands on hip. Her legs were long and shapely despite wearing white flat-soled sandals.

“No, that’s OK Louise it’s none of my business.” I turned and walked out the door. Sal was still organizing things in the back of the car. I just blurted it out to him: “What kind of shoes are New Exotica?”

“Our best customers are exotic dancers, strippers, and transvestites. The name of our store is New Exotica Emporium and this is our private label. But we ship worldwide under several different brands.” He closed the trunk and then asked me if I had a girlfriend. I said I had a couple. “Make sure I give you a catalog when we get to LA.”

This was starting to get strange and I was beginning to like it. By the time we had completely emptied the wagon half the load was in their room and the other half ended up in mine. “Grab the cooler and come on in to our room,” he said with a big smile. Those things were metal back in those days and much of the ice inside had turned to water. It made the thing heavy and unwieldy. It was still hot outside and I had actually broken into a sweat just carrying the thing 20 feet. The air conditioning in the room felt good as I pulled up the chair.

“Now I’ll have a beer” he said lying back on the bed. He offered me one again and this time I accepted, taking took two out handing him one. He reached over to the bag beside him and pulled out a container that contained marijuana cigarettes. He lit one up and passed it to me. This was after all the 1970s and smoking marijuana was in vogue. The wild weed was also a form of social and (sexual) currency, in much the same way cocaine was.

“Oh wow, Sal, it’s so great of you to share your weed.” I took a long deep toke and let the smoke tickle the bronchi and ciliae in my lungs before slowly exhaling. The rush I felt told me this was quality shit.

After a couple more hits I leaned back in the chair, now well under the influence. “Sal, man, it seems like you really know how to live.” He looked at me as if to say what would a kid like you really know about living? Then he kind of laughed and yelled to Weezie who was still in the bathroom. “Are you gonna want to smoke before we go out?” He lit up another number and now there were three stops that doobie had to make. That was a good thing for me because I was pretty wrecked just from sharing the first joint.

They had made plans to go to this famous steakhouse in Flagstaff. “We go there every year on our way to the convention. They only have waiters and they’re all cowboys.” She was beginning to beam as she described the place. “They’re wearing tight jeans and boots, why some are even wearing chaps.”

“If she had her way they’d be wearing spurs, too.” Sal added with a deep stoned laugh. She punched him playfully.

I was thinking a place like that in Flagstaff? I wondered if it was like that place in Denver Joe had described.

I could see they had a big night planned so I decided to take my leave. “Thanks, guys, for the buzz and the beers. I’m going to take a shower myself and then go across the street and grab a burger.” He offered me another beer to take with and I retired to my room. Then the munchies had a hold on me at that point so I chose to eat first. They had a Blake’s Whattaburger across the street and it was calling my name.

Once back in the room that shower was first in the order of priority. I had been toying with the idea of taking a short walk up the street to a bar at the end of the next block. I could hear its jukebox as I crossed the street to Blake’s. There were pickup trucks parked diagonally in front of that old brick saloon and in my stoned state they actually turned into horses; tied to a hitching post 100 years ago. Too stoned, I better not I thought shaking my head.

Back in the room the warm water cascading over my body was a welcomed sensation. So welcome I almost felt like a flower that had closed against the cold of an April night opening to drink in warm morning rain. Though the food had taken the edge of my condition I was still in a severely altered state.

Sometimes when I got stoned I would allow a little femininity into my life. My body was hair-free except for the blonde patch at the base of my belly. Since I wasn’t muscle bound there was tone and firmness. My physique had a shape and definition but my flesh was supple. My shoulders were broad and my legs were well-formed and strong from skiing and climbing hills as a kid. Now that I had washed away the road filth I was going to let the tub refill and take a bath as well. In those days Holiday Inns gave you a selection of toiletries in the bathroom and there was small bottle of bubble bath in the basket.

Soon after I slid into the bubbles and had enveloped myself with warm scented water the sensuality of it all turned my THC influenced mind to thoughts of sex. Soon my shapely penis was standing and sticking out of the water like a periscope. I found myself arching my back and sort of fucking the water. I grabbed it with my left hand delighting in how it filled my hand its proud helmet crowning my fist. Sometimes in such a stoned state I would have masturbated to climax but on this particular evening I wanted to be ready for anything. It wasn’t easy freeing myself from such a sybaritic indulgence, but I managed to towel off and to treat my dry skin to the body lotion they had. I applied the stuff liberally, trying not to miss anywhere.

The masturbation session in the bathtub had released a few hormones adding fuel to the fire that always seemed to be smoldering in my loins, stoned or sober. I was still hard and my scrotom was drawn up. When I got really stoned I always got horny. And when I got horny I sometimes got reckless. If I had a hard-on I would do anything. I had fantasized in the tub about Weezie sneaking into my room later that night wearing one of their negligees hot for my dick because Sal had passed out in a stoned stupor. Cock still hard and my mind on sex I found myself drawn to the stack of boxes along the wall. They were mostly shoe boxes. I opened several of them and the contents inside did not disappoint. True to the brand these shoes were exotic.

I found a size 9 and took one out of the box. It was jet black, patent leather, and spiked the full 5 inches. Holy Shit I whispered to myself. I sat down in the chair and put the right shoe on my foot. My heart was beating so loud I could almost hear it. My mouth had gone dry and my cock was throbbing. It fit! It fit perfectly. I grabbed the mate and put it on the other foot. Then I stood up. There was no pain from the toe box or slippage in the heel. The vamp of the shoe was cut just right so that I showed some toe cleavage. I carefully walked the two or three steps over to the full length mirror. I then rooted through the boxes looking for a pair of those fishnet stockings and a pair of lacy panties.

I copped a woman’s pose and spun around. If it weren’t for the cock I’d have a very appealing female body, I thought. At one point I lost my erection so I tucked my junk between my legs giving myself a fat pubis. I definitely would have fucked myself. In fact, if there were a male around I know I would have tumbled for him.

Images of the girls on the Rue de la Huchette in Paris came into my mind. I had gone there with my college French club. Not far from that street there was Boy Alley where I saw my first transsexual. They had the same thing working. Guys were in those windows showcasing their charms through transparent silk undergarments. Since most of the women on Huchette were old and gnarly, the boys were more attractive—they were slim and painted and pretty. Their male organs didn’t seem out of place at all. Their outwardly feminine bodies actually showcased their male equipment.

As the window curtains rustled in the early evening breeze, just like in Paris, I stood in the window. A hard cock filled the pink panties while the stilettos gave me 5 more inches of height. I had become six feet of hot nubile flesh. Clad in long nylons clad gams with patent leather high heels I think I could have lured a BYU football player in there. Soon dusk gave way to dark and I was still flouncing around like a girl in that room getting hotter and hornier and more reckless.

I heard the key being inserted but the door threw open too fast. It was them. Sal and Weezie stood there.

“Fuhhhhhhhk me!” Sal exclaimed incredulously. Weezie broke into a smile while Sal just stared.

I got that warm rush you feel in your stomach as adrenaline pours into your bloodstream. But I couldn’t fight and I couldn’t flee. My mouth got real dry once I had swallowed hard. I can only wonder what I must have looked like. I know my toes were pointed in like a nervous teenager. My skin was goosy and I was so petrified I couldn’t move. What I later learned was rectal flutter gripped my backside and I felt the sudden urge to defecate. What I was facing seemed the scariest of my young life.

There I was, my darkest side had been freed from an already flimsy tether and there I stood in a motel room in Arizona wearing provocative women’s undergarments and stiletto heels that belonged to people who had been kind enough to pick me up, and were intended for sale at a trade show.

“He’s got a boner, “Weezie said as she stood just behind him. “He must beliking this a lot.”

“Aren’t you a queer little bitch?” Sal just stood there slack-jawed but I could see the wheels turning as he was trying to process what he was seeing. Finally his face got red and a look of rage seemed to come across his face. “You love them; you just bought ‘em. Those shoes, the stockings, and the underwear are going to cost you $25. I hope you have it.”

“I do, I do, Sal,” I stammered. I didn’t really. “I have the money and I’ll pay you for them…for all of them.” My eyes cut from Sal to Weezie and back to Sal. If I had to give them $25 I wasn’t sure I’d be able to get to Santa Barbara.

“Now look at him,” Weezie said as she pointed at my groin. I had lost my erection. In fact my cock and my balls had retracted to the point where there was hardly any overt sign that a male was wearing those panties. “Now he looks like a real girl, doesn’t he?”

Sal’s eyes traced my body upward. The heat of his gaze could be felt as he went from south to north. I became aware that my bee sting male breasts were erect but my cock still stayed down. By then I had crossed my legs in self-consciousness and sat down on the bed, never taking my eyes off the two people who could (and would) completely have their way with me.

“Here’s our chance, baby.” Weezie whispered with her left hand on hip. Her body attitude was starting to turn sexual and after she uttered those words her right hand went up and finger-combed her long tresses. “You know, we’ve talked about all the boys who buy our stuff and how you’ve wanted to see them wear the stuff in our presence.”

He didn’t answer but it looked like he was started to get a rise from his own cock. A second or two later I was certain about his arousal, though it didn’t look like he had a big one. Good, I thought at least he won’t split me in two. I got the feeling almost immediately that this boy was going to get fucked like the girl I was allowing myself to be. It appeared I was going to be right.

“Turn around and let me see your ass.” Sal’s voice had a more even tone. It was low and slow more like a guy with a hard-on than angry. I lifted my arms up and turned on my toes. I actually wiggled my ass as the flush of arousal came back over me.

“OK, turn around,” he said.

I hesitated because I realized I was hard again. I turn slowly squeezing my thighs together and dropping my hands to cover the bulge. Weezie almost squealed in delight: “He’s hard again, Sal!”

“Michael, Michelle, whoever you are, get into our room.”

I moved in the direction of the adjoining door, quick timing it past the two of them. As I made a beeline toward the bed I felt their stares on my ass. I sat down facing them both as he starting tugging at his belt. “We should find out how much of a girl you really are.” Within seconds his shorts were down and a hard shapely penis was presented. He wrapped his left hand around it and ordered me to suck it.

By then I was so feminine and compliant I could have done a fraternity house. I wrapped my arms around his torso and took that six-inch beauty in my mouth. I took it all the way to the root and started going up and down that shaft like a bobble head. Maybe it was the lack of length of girth but I had no gag reflex to fight. His cock felt so incredibly natural and I was suckling like a baby on a mother’s breast.

Weezie stood off to the side giving me encouragement. “Suck it baby, just like a girl…that’s it baby, good good.” I began to hear moans and guttural groans from Sal as he was vigorously fucking my mouth.

“Sallie don’t you come. I can tell you’re about to come. Don’t you dare, Sal.”

He was about to cum. Twice I got a pre-cum appetizer that told me that the tangy entrée was about to be served. Then he pulled away and ordered me to bend over the back of the bed.

I felt the coolness of some kind of lubrication jelly applied to my anus followed by the sudden piercing of my rectal cavity by a foreign object of the kind I hadn’t experienced since two summers before in Colorado. It was better this time as if my body welcomed the return of a penis in the ass. Again, there was that uncomfortable bloating you get initially as the piston pumps air into your bowels and my rectal muscles still wanted to expel the intruder but in an instant that urge gave into the joy of receiving and pleasing another.

Face down; I was in an ideal position to orally work someone else as Weezie quickly surmised. She had by then stripped and jumped up onto the bed and positioned herself in such a way that her crotch was in my face. I stretched my body to try to reach her snatch but she kept inching back, almost taunting me with the sweet musky aroma of aroused pussy. All the while Sal hands held my hips the way butt-fuckers do (to keep the fuckee from pulling away) so I couldn’t get at her.

“Weezie, don’t do that. Make him lick your ass. If he wants something to lick, let him lick your asshole. Roll over.” I don’t think he ever broke rhythm while uttering those words. He pounded me and pounded me.

Her move was like the beautiful woman on the beach blanket beside you who makes a performance out of the simple act of turning over. The whole thing clicking into a man’s brain at the rate of 32 frames per second. Each one a snap shot of feminine grace and pulchritude. Each one would qualify for inclusion in the photo spread in some erotic man’s magazine.

Again she played keep away with me. Now I had her pink cherry and brown butt hole just beyond my tongues reach. Mercifully, she relented and the dank smell of poop residue and butt sweat hit my nostrils. Then my outstretch tongue hit the bulls eye and she squealed with delight at the tickling sensation of tongue on touch hole and involuntary jerked. I reached my arms forward and grasped her hips, which seemed to relax her and let my tongue glide north up her long butt crack. Once at the top I took a moment to lick her coccyx region and then brought the tongue back down, retracing my path. This time when my tongue got to her hole I rimmed her several times.

All the while, Sal kept reaming my ass from behind. By then I notice his balls were no longer slapping my perio region. He had picked up the pace. His breaths were now audible, and again Weezie turned and called out “Don’t come Sallie,” almost shouting over her shoulder but this time I was afraid he was too close to the edge to hold back. Then I realized I was getting close myself. The backside of my hard cock had been rubbing the bed spread and now there was more than just the sensation of a turgid cock. It was like every drop of blood in my body had descended on my groin and the pressure was building.

I loved what I was feeling now. With every thrust I parried. He was fucking me and I was fucking back and the frenulum nerve cluster just down from my pecker head was screaming in delight from the friction. With every withdrawal I followed him back, unwilling to allow his cock to leave my blissed out body.

“You bastard Sal, I want that come.” This time she flipped like a fish in a boat and just as I felt a blast of heat from Sal and felt him stiffen her muff was in my face. I recall that Weezie actually screamed as I pressed my nose against her clit and rammed tongue as far as it would reach deep into her sweet slippery vagina. Sal now had no control over his body and lunged forward on me like a dog. Weezie was then in an ideal position to lock us both together with her powerful legs. That girl was strong and hot.

No sooner did I inhale her engorged clitoris that she began to quiver.

Just as Sal’s tight body went loose I felt the familiar sensation of hot fluid pouring into my innards. He emitted a guttural “Aaah” as he drained his balls in my ass in three spasms the combination of all this sensory stimulation sent my own body into paroxysm and I felt the tingle. My prostate could no longer withstand the stimulation of Sal’s hard hot penis banging on it. A load of cum poured into my urethra and began the hot crawl to freedom, pushed along by long waves of deep muscle contractions I could feel from my calves to my upper torso..

Every time a man ejaculates he also expires a huge breath of uric acid laced carbon dioxide. That is always preceded by a big gulp of oxygen right soon after the semen is emitted by the prostate. However, in this case my nose and mouth were smothered by Weezie’s hot wet femininity and I was forced to experience for the first time the sensation that some gay men call ODO, oxygen deprivation orgasms.

Even though I couldn’t take that big breath, I still exhaled when the cum reached the end of my shaft, projecting a hot wave of breath in the direction of her entire genitalia. It was then that the sound of her screams went tinny and muffled. Lights flashed behind my closed eyes as wave after wave of spasms wracked my body expelling what felt like a quart of never ending spunk. For those brief seconds I have to think I was literally on death’s door, in a momentary state of suspended animation, and if I were to have died I think I might have even embraced it.

As quickly as I went out there, I returned.

Sensing that I might have been in distress, they both quickly cane to their senses. Weezie hitched back enough so that I could catch a breath and her right hand went down to her pussy and start working her clit in a circular motion. Back went her head and she moaned again, then again, humping the air, squeezing her legs together on her pumping hand and rolling onto her side still humping and shaking.

Meanwhile Sal had managed to roll off me and ended up on his back on the floor his chest heaving, eyes closed. Eventually, I began to get myself together. The first thing I noticed was a wet clammy feeling all over my belly and lower chest. I discovered that I had shot all over the bedspread and then rolled in it during the afterglow. I scooped what I could onto my two fingers and stuck them in Weezie’s mouth, for which she moaned with delight and then snapped her lips.

“Oooh, you have sweet cum, “ I heard her whisper.

As I clamored to my feet Sal remained on the floor, momentarily passed out. “Weezie is he alright?,” I asked part out of fear and part out of amazement that my little body has given him such pleasure.

“Oh yeah, he always passes out after sex. He’ll Wake up eventually. You must have been a great fuck he was really enjoying it.” It was then that I realized I still on those high heel shoes.” Bring those shoes over here I want to put them to another use.” I


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