If the Shoe Fits, Use It!

Weezie, a comely city girl from Chicago was a very sexual creature. Her boyfriend Sal owned a large and successful adult business on Halsted Street in Chicago. A large part of his trade was exotic underwear and clothing for hookers, transvestites, and fetishists not just in Chicagoland but nationwide. They were en route to a lingerie trade show in Los Angeles and picked me up along Interstate 40 just west of Albuquerque. I was hitchhiking out to Santa Barbara in the summer of 1976 from New England.

I assumed her given name was Louise, though she never said; and Sal just called her Weezie. The lady cleaned up well. By the time we had arrived in Flagstaff she was dusty, dirty and sweaty, as were we all. Me, especially. The El Camino they were driving had air conditioning but the cooling systems in that 1970 vintage wagon had little chance against the 100 degree plus temperature of the southwest in July.

However when she emerged from the bathroom showered, dressed and painted for an evening out she turned my head. She was pushing 40 judging by her eyes, which definitely had years in them. Probably those eyes had seem plenty, and judging by her reaction to our sexual escapade several minutes earlier so had her body.

Sal, the exotic apparel peddler from Chicago was still asleep on the floor after having reamed my gender bending asshole for a good ten minutes. She and Sal had returned to the motel early from their evening out. They found me flouncing around in some of their merchandise; specifically, a camisole, silk panties with belt, stockings and white stiletto high-heels. I had become increasingly aroused the longer I wore that stuff and when the door of the adjoining room flew open my hard cock was straining against the silkiness of the panties. Being in that state I was ripe for anybody who wanted to pluck me and Weezie picked up on that immediately. Sal appeared more focused on the fact that this hitchhiker they had rescued was tampering with his merchandise.

Apparently Sal had wanted to fuck a guy for a long time and Weezie must have been anxious to see it happen.

In minutes they had me in their bedroom and Sal was made me pay with my ass for allowing myself to be drawn to (and into) female lingerie and footwear. He ordered me to bend over the foot of the bed. Then he tore off the pink panties I had adorned and with my shapely butt in the air he sprayed some cool liquid onto my rear. Before I had time to prepare myself mentally I was startled by the searing pain of a penis being pushed into my bowels by a man filled with a cocktail of rage, lust and maybe a beer or two. I had eaten less than two hours earlier and there was lots of gas inside me. His piston packed my bowel with air, which is typical in the earliy stages of anal sex. A couple of involuntary farts later the pressure was relieved and I started to groove on it.

This was my second fucking and this time I reacted differently. Something inside me decided years ago when a hot cowboy had his way with me that getting butt-fucked was something to enjoy. As soon as the pain subsided I caught up with his rhythm and I was giving as well as I was getting. I was moaning, groaning, and grunting clasping the bed linens in my fist and trying to avoid suffocation due to my face being pushed into the bed. Before long I was prone, my legs were splayed, and my lower torso was grinding my pulsating cock into the bed spread. However, through it all those white pumps remained on my feet.

Weezie began shouting at Sal about not cumming yet.

I soon realized she had positioned herself practically astride my head. She grabbed my long blonde hair and pulled my face up. “Eat my pussy while he’s fucking you, you sweet little queer.”

Yeah I guess I was a queer; but at that moment I was relishing my deviance. If being “queer” was this great then let it be. Right then I had a mouthful of swollen clitoris, and my tongue was darting in and out of her musky vagina. A bear of a man was covering me from behind and filling my body with warmth that I welcomed with every thrust and parry. Had I been in charge of this scene I would have backed him up against the wall and impaled myself the way I do now to the dildo stuck I stick on the wall or the cocks that protrude through the glory holes at the video store where I frequent.

Eventually we all came at about the same time. His hot spunk bathed my rectum in warmth of a liquid nature. Hearing Sal emit a loud and long “o-o-o-h” was enough for Weezie to pop her cork and my tongue was soon awash in her pussy juice. So much that I had to swallow as if I had taken a man’s load. I think I actually started the process by stretching my stiletto clad legs and pumping against the bedspread in order to induce an orgasm for myself. As I gulped air in between tongue swipes of Weezie’s clit, my cock filled with thick cum and then blew it out. I must have pumped two tablespoons onto that bedspread.

Fast forward five minutes.

Sal is passed out on the floor—still. Weezie however, was just getting started. She shouted: “Fuck me with a shoe.” At first I was perplexed. Then she repeated herself. “Fuck me with that goddamn shoe!” I pulled the left shoe off and lifted it up as if to ask How do you want me to do it? “Stick the toe in my cunt,” she said with a breathless urgency that I took seriously. “Stick it in there all the way to the heel.” I obeyed. To my amazement it went all the way in. “Oh, fuck yes…that’s it,” she said throwing her head back and lifting her buttocks several inches off the bed clothes. “Can you get it in any farther?”

“I don’t think so, Weezie.” I’m sure I looked like an inexperienced virgin to her

“OK, come up here so I can suck your cock.” I hesitated. “Don’t worry I’ll fuck myself with the shoe. I just want to suck on that cock while I’m doing it.”

My weapon had just fired only a few minutes prior but once it got into her mouth it quickly hardened up. And could that woman suck cock? Her left hand was pumping that shoe into her cunt. Her right hand was squeezing my ass cheek, and her mouth was taking me to Heaven. Imagine a baby calf suckling on your finger.

She went into ecstasy, but never stopped bobbing her head and working her tongue. I remember wondering how this would look to Sal if he were to awaken. I wished I could I could be watching it and doing it. It occurred to me that there was a mirror on the wall behind me. Since her eyes were closed I stole a peek backward and I’ll never forget the look of a summer-white woman’s pump half buried in a dark hairy pussy.

At that point she had let go of the shoe and both her hands were now on me. I reached back to help her with the shoe but she grabbed my arm and shook her head as if to say no, and gave me a close-mouthed “um-um.” Right about then she picked up the pace of her fellatio. Both hands were on my ass cheeks pushing my cock deep into her throat. She started writhing and vocalizing. I began to pump her mouth furiously until I got a tingle and a hot flash. Just as I began to fill my tube with a fresh load of poon she pulled off my cock and grabbed it with her right hand. She pumped it three or four times and then put her face in position to both see the ejaculation and to get a facial. Her left hand had gone back to the shoe.

I loosed a load all over her nose and upper lip. I had good volume considering I had cum no more than 15 minutes earlier.Just as the jizz was hitting her face she arched her back, threw back her back, and let out a long soulful groan. Then I heard a squishing sound, followed by a small crack somewhere behind us. However I was still in the throes of orgasm, collapsed against the headboard so as not to crash down on her, spent and semi-conscious. By the time I opened my eyes she had started gathering up my spunk with her fingers and was licking them. After the usual post-coital superlatives and exclamations I got around to asking her about the noise I heard.

“It was the shoe,” she said with a smile and then a little giggle.

“The shoe? Whaddya’ mean the shoe?” I couldn’t tell whether she was messing with me or not?

Giving me a little shove she said: “Look around.” I turned backwards. “Do you see that shoe anywhere?” There was a look of both pride and bemusement on her face.

I scrambled to my feet—careful not to step on the still prostrate Sal—and found the shoe on the floor between the foot of the bed and the dresser. I bent down and picked it up.

She was till beaming as I jumped back on the bed and began to present the shoe to her, still incredulous. Her eyebrows were raised.

“Go ahead put it in your mouth. It’s covered with my cum.” Those brown eyes were as big as her grin.

By then I was satiated. I had exorcised myself. The demons had been banished, and the fog of sexual madness had cleared. I began to ponder what had just taken place. Here is this wet shoe that had been used as a sex toy and then launched four feet out of a violently contracting vagina. I am wearing a garter belt and nylon stockings. There is a guy passed out on the carpet. My ass is dilated from having been well fucked by a thick penis. And the guy’s wife is naked, has just finished blowing me and a shoe out of her vagina and onto the floor, and is lying there blissed-out.

In the course of taking stock I realized my throat was parched—maybe from the arid air, maybe from the altitude of Flagstaff—probably due to dehydration. “Are there any more beers left in the cooler?” I asked Weezie.

“There should be,” she replied. As I walked toward the cooler she added: “Grab one for me while you’re there.” I pulled a couple of Coors Banquet brews from the now melted-but-still cold water in the cooler. There is nothing like barley pop when you’re dehydrated; and Coors was always a great palliative for desert mouth. I remember those beers we drank there in Flagstaff well because it was the first time I had seen a push tab on a beverage can. Coors had just introduced them (they never grabbed hold) and I struggled with them. Weezie ended up opening them smoothly and I ended up slightly embarrassed. I should say more embarrassed. I proposed a toast to “new experiences.” We banged our aluminum cans together and she answered with: “To another experience.” After her first sip she turned to me and said, “You know, I can tell you’re trying to make sense of what just happened.”

After thinking for a second I said, “I’m…no no…I’m OK with it.” Her response with the words I don’t believe you were exactly what I suspected she was thinking. “I had gotten horny wearing that stuff and wanted something to happen…anything, I guess.”

“Yeah, well you can take the stockings off now.” She said with that impish grin. With a sniff and a snort, I popped the garters and carefully rolled down the nylons careful not to cause a run. She watched me intently. As I stood up she whispered. “You have great legs.” Her voice trailed off. I felt myself blush. Then she completed the thought: “In fact, you have a great body overall.”

“Aren’t guys supposed to be lean, muscular, and shaped like…” I paused. “You know, like men.” I know I must have had an inquiring look as I said that.

True to the increasingly androgynous 1970’s (this was 1976) she answered: “All that macho shit.” She nodded at Sal now snoring on the floor. “He’s really like that. He has wanted to fuck a boy for a long time. Truth-be-told, he probably already had—maybe more than one. And when we talk about it, or some of the cute boys who come into the store, he goes through this thing where he questions his masculinity.”

She went on to tell me that she works the front of the store and Sal stays in the office handling the business end of things. She told me that he had two-way mirrors. One looked out on the sales floor. The other looked into the changing booth. “He is such a voyeur,” she said matter-of-factly with a hint of frustration in her voice.

“You mean he can watch people trying on stuff?” I said, astonished.

“He can, and he does, all the time.” I was so amazed I was speechless. More amazing was that my battle-weary pecker was starting to stir again. “He takes his penis out and whacks off right at his desk. I have caught him doing it a couple of times.” I could see a myriad of possibilities in that kind of set-up.

“I can tell when he’s done it because he has no interest in me that night.” I answered as most men would with that sucks. I listened intently as she continued. “We actually get more men in the shop than women but that doesn’t seem to matter to him. A couple of times I have actually gone into the dressing room and done guys ‘cuz I knew was watching. I even did a girl one time.”

“Oh fuck, Weezie” I said breathelessly, now very conscious of the erection I had.

Her eyes dropped. “Yeah, you like that don’t you. You guys are so fucking visual. That’s what Sal always says: Sorry, Weezie, but I’m visual.”

“We are, I guess.”

She continued. “I really lovethat those guys have an outlet for their true selves. They are really sweet, and oh so good looking.” She got this dreamy look as she stared into space for a second or two. She turned to me with a smile. “ If you came to our shop, I’d make you look killer.”

I smiled, “I’d need lots of makeup. You do make-up too?”

“Oh yeah,” she said, “On Fridays and Saturdays they need appointments to get with me. And of course, Sunday is the amateur day at the drag club down the street.” She turned to me and inspected my face. “You had acne, didn’t you?” I nodded. “But you have this little boy face and I love your eyes.” She grasped my face and planted a kiss on my right eye. “The minute our eyes met out there on the road I started figuring how I could get my hands on you.”

“I bet you’re surprised at the way you got your hands on me.” I said off-handedly.

“A little. You know how rock stars sometimes dress and act like girls. I really like the New York Dolls, Lou Reed, Bowie, and all those dudes. I love Mick Jagger, too, and Steven Tyler from the new band Aerosmith. You carry yourself that sort of way.

“You mean I’m girlish?” I said that not wholly sure I wanted to hear the answer. But I had discovered there was something very erotic about prancing around in that lingerie. And I had often look at musicians and wondered what they were into sexually, and I suspected that whatever it was I would probably like it, too.

“You have a female side. I have a male side. Trouble is most guys are afraid of their female sides.”

“Sal didn’t seem too afraid of his female side a few minutes ago,” I answered sarcastically.

“What he did wasn’t female it was a power thing, a very male thing. He had you in a compromising place and he took advantage of it.” I told Weezie that I had not only allowed myself to be taken by men before but that I had provoked it. I shared stories of all the playing I had done with the same sex. Her answer was: “Hey, you like cock. Cock is good. I like pussy, too. We’re all human and what feels good to one gender feels just as good to the other gender.”

It was so nice being able to talk to Weezie. Looking back I couldn’t imagine having to process that evening alone in that room next door. And talk we did. We talked in depth about sexuality and truth. I’ll always remember another thing she said: “You can bullshit people and you can bullshit your brain. But you can’t bullshit your body.” From that evening and our 50-minute girl take I gained new perspectives. She lived in a huge city. She worked with people every day that had kinks in their hoses. Some indulged them, some battled them, some denied them; all were aware of them and she got so she could almost classify each the second they walked into the store. It sounded like a satisfying business.

After about an hour had passed Sal started coming back to life. “Does he always just collapse on the floor after sex?” I asked in a whisper.

“Fucking is tough on his back. He has a screwed up spine and stretching out on the floor prevents his going into spasms.”

His head popped up. He looked over at us sitting on the bed. “What the fuck?” he asked, but we both understood that he knew the fuck.

Weezie put on her best compassionate expression. “Hi, babe, how’s your back?”

“It’s OK.” Then he looked at me, looked at Weezie, then his eyes cut back to me. “How come he’s still in here?” Sal’s reaction wasn’t unexpected. Weezie had prepared me.

“Sal, is that any way to talked to someone who just took your dick in his ass?” Weezie came to my defense and I appreciated it.

“He fucking raided our product without asking me. I’d do the same thing to any of those Halsted hippies who came into the store and stole from me.” That went to the point she made about gender-bending guys with long hair, slender bodies, and a feminine side.

“It’s a good thing I’m there, Sal. Who knows what you might have done.”

“You liked it didn’t you, you little slut.” He stared hard into my eyes. His look was intimidating but I had the presence of mind to answer yes, and succinctly diffuse the situation with the one thing that universally puts out fires: The opportunity to make money.

“I guess I’m no different from most the guys you get your store. I’m beginning to see that I get pleasure from being girly. I could become a good customer of yours.”

“Well you still owe me $25 for that stuff.” He said as he walked in a huff into the bathroom.

Weezie gave me a look that said everything was cool. She then lifted her voice toward the bathroom. “Sal, his bed is covered with boxes. Can he sleep in here?” She shouted to him over the sound of a healthy piss stream flowing out of that big peephole that graced the end of his heavy meat. No answer.

“Ok, but I’m sleeping in the middle. I don’t want him getting at you in the middle of the night.”

“How do you know he hasn’t already?” She looked at me and we both sort of giggled.

“I know you Weezie. The way you scream and carry on. I would have waked up.”

I asked for permission to go brush my teeth and splash my face. I could hear them talking in low tones while I was in my bathroom. Since I was still unsure about things, before I re-entered their room I asked again: “Are you sure it’s OK?”

Weezie was giving him a look that said only one word could be uttered: Yes. “Yeah, what the fuck.” He said with a dismissive sigh. Sal motioned me on in. He had climbed into the middle of the queen bed. In those days king beds were to be found only in the better hotels. His eyes followed me as I gave him my best feminine strut. “Maybe I’ll fuck you again.” Weezie punched him in the arm and called him a shit. Then I sat on the edge with my back to him, closed my legs like a lady and pivoted on my rounded shapely ass giving him a quick glance at my legs and the blonde bush between them. My penis had contracted and was accordioned along with my scrotum between my thighs pretty much out of view.

Weezie was right on that comment with the typical response: “If anyone gets fucked tonight it’s gonna be me. You hear that Sal?”

“He’s got a better ass than you got, Weezie.” He chortled and surreptitiously grabbed my junk. Afraid of getting a rise from it, I pulled away and rolled over, turning out the lamp on the end table. I made a mental note that the bottle of Anal-Eze lubricant was still on the end table. Anal-Eze, strange that they kept it handy ( I later learned the Weezie liked it in the ass, too).

We all went to sleep quickly and remained asleep for five hours. As the first light of a desert dawn began filling the gaps between the blinds I awoke to find myself spooning with Sal. Despite my dalliances with the same sex I had never actually slept with a man. His body was big and it was warm. The air-conditioner had been running full-blast all night and it was actually a little cool in that room. My right hand was draped over his hip resting on his abdomen. He had a blaze of hair over breast bone and the feel of that was an entirely new sensation for my tactile fingertips. Weezie was still deeply asleep on the other side of him.

I think Sal may have sensed that I was awake. He adjusted his body in such a way that I could easily slide my hand down his belly to his crotch. I, in turn snuggled and pushed my thighs up tight against his. At that point nature took over and my hand began it inevitable journey a few inches to the south, to the promised land of thick male meat and big balls. By the time I got there I was rewarded by a completely tumescent penis that welcomed my hand by giving up a couple droplets of pre-fuck that I pilled around the head of that sweet scepter with my thumb.

Of course, I returned the favor by teasing his naked ass crack with a similarly hard and hot rod that I deftly maneuvered up, down, and all around his bunghole. At the point where my cock hit the bull’s-eye he moaned and backed up as if to encourage me to push that cock in. In a move that I still marvel at I managed to twist my upper body to the right while keeping my dick positioned squarely at the gates. I grabbed the bottle of lubricant and expressed a copious amount of the cool liquid into my hand. I then pulled back, slathered his bottom with some of it, put the stuff in the palm of my hand on my dick. Again I knocked on his back door. With a loud grunt and an “aaaah” that I am surprised didn’t wake Weezie his ass easily gave way. Instantly I was in his spacious rectal chamber and I suspected I wasn’t the first to go there. I emitted an long drawn out “oh.” He immediately began grinding his ass back as I began pumping, slowly at first. All the while I was stroking his hard cock almost in rhythm with my hip thrusts. Before long he was in a state where lust had taken hold. We both were.

Weezie suddenly stirred and whispered something neither of us could understand. I stopped the fucking. Which I think was probably a good thing because we were both Hell-bent for orgasms by that point and needed to slow our roll. The room was thick with endorphins that even a sleeping beauty could sense. Instinctively, she rolled toward Sal and reached out for his groin they way good partners do. I am sure she was used to morning glories but the fact that she found another hand wrapped around Sal’s root must have startled her.

Her reaction was actually a pleasant surprise.

“I see you two are getting better acquainted,” she whispered, a smile coming over her face, eyes still closed still in a state of half-sleep. Rather than compete with my hand on his shaft, she simply began stroking his balls and perianal region, only to discover that his back and forth movements were attributable to a cock in his asshole. “Oh my God, Sallie he’s fucking you.”

Once the horse bolted from the barn things got wild in that bed.

Weezie woke up in an instant. She threw back the covers and took a closer look. As she peered over his hips I stopped shagging. “No, No, baby don’t stop. I want to see this. Fuck him. Really fuck him, Michael.” I started up again. “Oh my fucking word. Sallie does it feel good.” All he could muster was a moan. “Oh yeah, I bet that cock feels real good in your tight little ass.”

I just pumped and pumped his well-lubed exit hole. I was also glad I had cum twice the night before because so far there were no signs of an impending orgasm, but I thought he was about to pop from the workout I was giving his prostate. With a quick move Weezie rolled onto her left side and backed up her butt to Sal’s turgid cock. In no time she had coupled with him and the sandwich was complete.

I can only imagine what it might have been like had there been anyone in the next room or above us. The three of us were lost in total ecstasy, carnally carrying on with an abandon few people can imagine, much less ever get to experience. Sal was getting it and giving it, which is an experience that almost defies description in any language.

Had I been next door I’d have been jerking off and envious as Hell.

There was heaving breathing; moaning and groaning. Sal had been right about Weezie. Once his cock got inside her she went bananas. At one point I felt her arms reach behind me and her finger penetrate my ass. How could she…how could we be doing all this stuff and not lose it.

Then like a clap of thunder, Weezie popped with that squishing sound I had heard before the shoe flew across the room. She soon rolled over on her back instantly pulling Sal off my cock and onto her body. She was writhing out of control, her legs flailing wildly, her heels kicking the mattress. Sal was struggling to keep up with his freak of a girlfriend. But, oh! What a sight it was. He pumped her. Slap, Slap, Squish. All the sounds of wild sex were coming from those two sybarites. The smell sex was in the air. I clamored to my knees and started furiously pounding my cock above them. . I wanted to loosen my load. I wanted to cum all over them. Before long it happened. A massive wave began to build. My body went into catharsis. I aimed for Sal’s ass. The first spurt crashed against his right cheek, the second one rained in his ass crack only to drip down to the still distended orifice. Feeling what he knew was cum was all it took to start his orgasm. He banged Weezie four or five more times. Then his body stiffened. With a loud groan he emptied his balls into her hot flooded femininity. As I continued to pump the last few droplets of joy juice out of my cock, the two of them fell into a languorous, delicious afterglow.

Once satisfied that there was nothing left inside me I dropped onto the bed and burrowed my way into the flesh pile the way a young puppy does at feeding time.

Exhausted and sated all three of us closed our eyes, not to re awaken for two more hours.

TO BE CONTINUED IN THE CONCLUDING CHAPTER: ON BEING HIS SALES ASSISTANT AT A LINGERIE TRADE SHOW