Danny had been acting weird for the past three days. He was jittery and excited, easily distracted and very cryptic about what he’d been up to. I was vacuuming the carpet and watching him out of the corner of my eye as he tried closing out the register. This was his own father’s shoe store and Danny had been closing out the cash drawer all summer but tonight, in the peculiar mood that he was in, he just couldn’t get it right. I wrapped the cord around the old Hoover and put it in the stockroom. As I walked over to the counter I heard Danny muttering, “Damn, damn, damn,” and hitting keys like it was his first time using the cash register.
“Get out of the way.” I said, shouldering him aside. “What’s with you, anyway? You’ve been screwing up and acting like an asshole for the last couple of days and now you’ve gotten so stupid you can’t even do this.” I realized how harsh I must have sounded, especially to the boss’s son, but Danny and I had been friends forever and I felt that he was hiding something from me. I pulled the tape, tallied the total and quickly counted the money. “You’re twelve dollars short,” I informed him.
“Shit,” he said as he scribbled an I.O.U. and signed it.
“Are you gonna be a mess for much longer? What’s up with you anyway? Are you getting laid or something?” I barked at him as I prepared the deposit and tomorrow’s bank.
Danny looked from my fast moving hands to my face and paused, as if gauging the strength of our friendship. I was a little hurt that he’d even feel the need for that second’s worth of appraisal. Finally he sighed and said, “Uh, sorta.”
“What question are you ‘sorta’ answering?” I asked.
“The last one. I had sex but it was more of a practice than the real thing.” He grinned at my perplexed reaction.
“What are you talking about?” I asked, intrigued and annoyed by his beating around the bush.
We went through all the usual vowing and swearing secrecy that we’d done since childhood before he finally said, “Listen, let me make a call first, then maybe explaining won’t be necessary.” While he used the phone in the back I took care of all the last minute details that had to be done to close shop for the night. He emerged from the stockroom looking more gleeful than he’d been all day. “It’s okay, you can come with me. If you don’t want to join in, it’s cool, but remember your promise to never ever say anything about this to anybody, ever.”
All through the fifteen minute drive through parts of town we usually avoided, he kept making me swear; on my mother’s grave, my eyes, the heads of my children (when I had them. I hadn’t even gotten into a girls’ pants yet). I couldn’t’ recall him ever being so emphatic about anything in all the years we’d been friends. Finally, we pulled up to a rundown motel and parked the car. He turned to me, again assessing my trustworthiness and sighed. “It’s like a practice run for when we get girls,” he said solemnly. “This way we’ll know what to do and how to act. Like I said, you don’t have to participate if you don’t want to, but you’ve still got to strip down to your underwear if you want to watch. That’s the deal I made with her and if you’re not sure you can just wait in the car until I finish.”
I was dying of curiosity and agreed to the conditions he had outlined. We got out of the car and headed towards the last door of the shabby motel, Danny squeezing his cock in anticipation. I was nervous and hesitant but watching Danny maul his member through his chinos made me excited, too.
When we entered the room it was dark and smoky and there was a thin woman lying on the bed wearing only a pair of stockings. Danny began quietly stripping off his clothes and motioned me to follow suit. The woman on the bed seemed vaguely familiar but it wasn’t until I was down to my briefs that I realized that it wasn’t a woman at all. It was a shoe salesman who’d come into the store earlier in the week trying to convince Danny’s dad to carry his line of ladies’ sandals. My boss had been curt and dismissive with the man, later telling Danny and me that he didn’t deal with “fruits.” This guy, Ronnie, now lay stretched out on the cheap motel bed, nude, except for the silk hose encasing his feminine legs and he was making silly little woman-like gestures towards us. My stomach lurched at the significance of us being in the same room as this person but Danny was suffering no such pangs of disgust. He shucked off his drawers, his large cock already swollen and swaying as he guided me to a chair near the bed and gently pushed me into it.
“Remember, just sit and watch if you’re too chicken. It’s good practice for later,” he whispered before turning his attention to the person in the bed.
It was kinda hard to see anything clearly because there was a red scarf draped over the lamp and there was almost a fog created by five or six burning incense sticks around the room. Danny lay on top of the guy and began kissing and humping him while the salesman cooed and encouraged him in a somewhat husky but feminine voice. I wanted to look away, because I didn’t want to see my friend in such perverse circumstances but I couldn’t stop gawking in morbid fascination. When Danny rolled off Ronnie I could see his thick, rigid cock bobbing before him. He caught me staring and gave me a wink and a wicked smile. Ronnie had produced a jar of Vaseline from somewhere and was rubbing the greasy substance into the crack of his ass and was coating Danny’s throbbing tool with more of the pungent jelly. Ronnie rolled over on his stomach and wiggled his buttocks, as Danny got on his knees ready to mount him.
“Oh, yes, stud,” purred the females substitute, “I’ve been dreaming all day about your cock in my pussy. Put that big dick in my juicy cunt. Make me feel like the woman I am.” Ronnie’s throaty moans followed as my buddy pressed his boner into the slick gap between his ass cheeks. Danny started fucking the mewling he/she, pounding and thrusting into the mock vagina. My own prick was hard and leaking as I rose from the chair to better watch the sticky hunk of veined meat penetrating deep into Ronnie’s cunt. Danny would pull the shaft all the way out, just leaving the helmet imbedding in the grasping ring of Ronnie’s “pussy,” so I could get a good view of the proceedings. Danny must have been getting a lot of “practice” because it sure looked like professional fucking to me. When he came, his grunts drowned out the whimpers emanating from Ronnie’s suspiciously red lips.
Danny got up, squeezing a last glob of his semen onto Ronnie’s quivering ass cheeks and smiled broadly at me. “Go ahead, Dean. I got her all warmed up for you. She likes to make out for awhile before giving it up because she’s one of those ‘nice’ girls, aren’t you, Ronnie?”
As Danny headed off to the bathroom to wash his gooey, dripping cock, Ronnie rolled over on his back and beckoned me to lie on top of him. I was really horny, having never done more than kiss a girl and jerk off by myself, but still I hesitated.
Ronnie gave me a sulky smile and leaned forward, pushing my underpants down to my knees. “I can see you’re afraid. Don’t be. A woman like me knows how to treat first-timers,” she murmured as she stroked my rock hard prick. “Are you shy because your penis isn’t as big as your friend’s? I think it’s pretty and it will grow, you’ll see. Now come over here and lie down with me and give me a kiss.”
I kissed Ronnie’s lips; tasting the lipstick and feeling his tongue slide past my front teeth. My boner touched his as I began humping into his bush. I was still so nervous about this activity that I wasn’t sure I’d be able to continue and it was hard trying to imagine Ronnie was a woman when I could feel our penises bumping together. I started licking Ronnie’s titties after he muttered that I should and when I repositioned to get some more tongue-kissing practice I was shocked to find Danny’s prick going in and out of Ronnie’s mouth. It was right there in front of me, his long, hard cock being licked and sucked. I felt Ronnie’s cool fingers pressing my buttocks, mashing our cocks together and I could smell the soap scent coming from Danny’s recently washed genitals and I shot my sperm all over Ronnie’s belly.
For the next week it was all I could talk about with Danny whenever we were alone. I even started referring to Ronnie as “she” the way Danny did. Ronnie had checked out of the motel by the following day so I never got to actually put my dick inside her so I was bugging Danny about how it felt and what he thought about the whole incident. I pestered him about the stockings that Ronnie wore also because the silk felt so incredible against my thighs while I was pumping her. When Danny’s family headed out west to visit his married sister for two weeks, Danny suggested I stay over at his place. Of course, being lifelong friends, I had spent many nights at his place. They had a guestroom which they even dubbed “Dean’s Wing.”
After the first day of working alone we went back to his house and had dinner and then played cards while the TV droned on in the next room. I kept talking about Ronnie, but Danny said we’d discuss it later. Around ten o’clock we headed upstairs, took our showers and met in his room to talk before going to bed. We sat on his bed and I immediately brought up the subject of the stockings. I told Danny that Ronnie probably wore them to disguise his leg hair but he must have liked it, too.
Danny looked at me and said, “you’re probably right. It does feel pretty sexy to slip into a pair of stockings.” He reached into the drawer of the nightstand and pulled out a crumbled ball of beige, transparent nylon. “You’ve been talking about it so much I found these in my sister’s old clothes. I even tried them on. It felt nice all right but my legs are too hairy and the hairs were poking out everywhere. Why don’t you try them on and see how they feel?”
“You tried them on?” I asked.
“Yeah, go ahead, it’s no big deal.” Danny put the hosiery in my hand. I looked at them. Slowly, I began pulling them on the way I’d seen my mother do. The sheer fabric made the little blond hairs on my legs disappear and the sensation was startlingly exciting.
“Stand up and let me see,” Danny said in a stranger, lower voice than usual. I got up and stood in front of him. He stroked my legs. “Wow, your legs look fucking great. Really, and they feel really nice.”
I felt kind of strange having Danny feeling up my nylon-clad legs, but I also liked the feeling. He leaned back and I noticed that the front of his underwear were obscenely distended. I also noted that I had a growing bulge.
“That just doesn’t look right with those white jockey shorts,” he said as he opened the drawer again, fished around and selected a pair of black, lacy panties. He held them out to me.
“I’m not putting those on!” I exclaimed. “That’s ... I don’t know ... but it would be ... ” I was choking on my words.
“Come on, relax. What’s the big deal? I put them on a couple of times and it really got me hard. It feels sexy, that’s all. Come on; put them on for a minute. You’ll see ... it’s not such a big deal.” Danny pleaded with me.
He’d always been the guy in charge. He could talk me into anything. I tried to ignore the heat from my blushing ears and neck and slowly pushed my underwear down to my ankles. Then I stepped out of them. I didn’t look at Danny again until the panties were snugly fitted around my ass and hardening cock.
“Feels really good, doesn’t it?” Danny asked, gazing at my panty- and-nylon-clad lower half and lightly fingering his obvious hard on. I just nodded, afraid to speak.
“Turn around and let me see the back,” Danny said. I did as he requested and was about to call off this whole bizarre session when he came up behind me and began rubbing my lace-covered butt cheeks with tentative fingers. “Goddamn, you look more like a girl than Ronnie did, from the back. And you feel so soft and sexy. Turn around.”
When I did, I saw that he had taken off his briefs and was sporting a roaring 10-inch hard-on. “Push your cock back between your legs,” he whispered excitedly. I did and only the wispy hairs of my pubes showed through the panties. Pushing my hard cock back that way created a fold in my crotch that looked like a cunt. Danny came up to me and pressed his cock against my pubic bone and then he sighed and put his arms around my waist as he ground his meat against the hairy V created by my cock tucking. My arms were up and I didn’t know what to do with them so I held his shoulders and we stood there, ear to ear, both of breathing irregularly. Then Danny reached down and inserted his cock through the leg hole in the panties. Now there wasn’t even the pretense of material separating his tool from my bare flesh. The tension from the leg band pushed his thick hard-on against my bare skin and I shuddered, clutching him tightly to keep from toppling over because my legs were suddenly weak. Then Danny licked my neck and ear and soon his mouth found mine and we began kissing wetly, sliding our tongues inside each other’s mouths. We stood that way, swaying and sliding our sweaty bodies against each other.
“Okay,” I said, “we’d better stop.”
“Well, for one thing, my dick is beginning to hurt, twisted like that.” I said. Before I could say anything else, Danny had maneuvered us onto the bed.
“Put your cock where it’s comfortable,” he said. “Why don’t you lie on your stomach? God, I’m so fuckin’ hot!”
For some reason, I couldn’t speak. I knew this was wrong, yet it felt so fucking good. I just couldn’t stop what was happening. I turned onto my stomach. Danny began stroking my legs and butt and back. I felt him climb on top of me. Once again, he slipped his big, thick cock through the tight leg hole and was pressing it into my moist ass crack. I was beginning to sweat, big time. His huge dick felt like velvet as he slowly sawed it back and forth between my plump, panty-clad cheeks. He licked my neck and ear, nuzzling me with his hot breath.
“You okay?” he whispered.
“I dunno ... maybe we should stop,” I said. He reached under me and squeezed my cock.
“Tonight, you be the girl. Then we can switch later. You okay with that?”
“Uh, guess so ... if you ... ” I garbled my words. My thoughts were fragmented as my skin sent electric messages all over my trembling body.
“Yeah, you’re my girl,” he whispered, continuing to slowly slide his now-slick boner between my ass cheeks. “If I want something from my girl, I can have it, can’t I? Don’t you want to please me?” His weight and motion of his thick cock sliding back and forth across my fluttering asshole prevented me from speaking. “Tell me that you like it. Tell me that you love my cock against your hot pussyhole! Tell me that you love my big cock touching your pussy,” Danny chanted as he dry-humped me.
“Yes,” I whispered. “Yes. I like your cock next to my pussyhole,” I found myself saying. I was mesmerized at his cock so close to my cunt ... I mean, my asshole.
“Are you my girl?” he whispered.
“Yeah, yeah Danny. I’m your girl,” I answered and felt like crying.
“You know what I want,” he growled, pulling his cock from the panties. “Let me get some Vaseline. You want it, don’t you?”
My body stiffened in response. I knew what he wanted. He wanted to fuck my virgin boy-pussy the way he’d fucked Ronnie. He began kissing my neck again, and licking my ears, tonguing my cheek and I relaxed again as he got up and went into the bathroom. Soon he was back and he spread my legs as he knelt behind me. My eyes were tightly shut as he yanked down the sweat-soaked panties to mid-thigh. The sound of the cap of the Vaseline being placed on the table made my body tremble. He responded by whispering softly as his greased fingers began massaging my crack. He moved really slowly as he slathered the tender valley between my round cheeks and then he began working a glob of the stuff right over my asshole. I gasped as his finger poked through my oiled asslips and I felt it slowly entering my ass.
“Yeah, that’s it. Squeeze your pussy tight,” he instructed as his finger began probing and sliding back and forth. I tried to relax, and felt another finger enter my ass. “Oh, yeah, I love that pussy,” he whispered. “I love my girl’s tight pussy hole,” he crooned as he finger-fucked me, his fingers going deeper and deeper.
He mounted me, guiding his huge prong to the entrance of my greased cunt. As I felt his big cockhead slide past my tight cuntlips, I felt cum spurting from my cock. Danny was so intent on packing the entire length of his monster bone into my Vaseline smeared orifice that he didn’t notice. I lay there motionless while he painlessly finished stuffing that huge dick into me and then he began slow, swirling fuck thrusts into my pussy. “Squeeze your ass, tighten you ass,” he whispered as he fucked me. My pussylips grasped and clutched at his pistoning plowboy and I began to feel a delirious thrill swelling from inside my guts with each stroke.
He reached under me to grope for my boner and instead, found my limp cock swimming in a thick pool of cum. “You came, you came already,” he whispered excitedly. “Wow, I’m gonna spray your cunt with my cockjuice.” He thrust harder and faster. “You want it? You want my cum in your hot pussyhole?” he panted.
“No ... ” I moaned as he began dicking me even more vigorously. “Don’t ... please ... stop ... no ... I don’t want you to ... ” I panted. For some reason I didn’t want him to shoot inside of my ass. Maybe if we stopped now ... maybe this wouldn’t be what it seemed. “Danny, please ... no ... ” I couldn’t finish because I was crying, sobbing with shame and fear ... ”
“Shhh, it’s okay ... don’t worry,” he whispered. “I won’t come inside you. I thought you wanted it ... Shhh, don’t cry. I’ll stop. You’re my girl and I want you to be happy. Don’t worry, baby. Maybe you’ll want it later. I’ll go real slow ... I want my cream inside of you ... maybe later ...
And later, he shot his load into my ass. And he’s still fucking his girl, who loves it. And you should see my lingerie collection.
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