This is a print version of story Daddy's Popper Challenge by gypsy61 from

Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossdresser Hosting, Submissive and Kinky, Hosting." Good description but no pictures, still though, but I had a good feeling. It had just gone up twenty minutes ago; suddenly a little horny I filled it in my "maybe later" box and went back to work. Around 4 work slowed and I took another look at the ad, on just a gut feeling I replied "Did you get any gentlemen callers? I’m getting off work soon, want me to come over and play daddy for a while?” I included two decent pics and sent it off, either she was already engaged or I might get a decent blowjob to get my mind off work.

A little later she responded, her name was Danielle and one person had already flaked on her. I said I could come over right after work, let's meet and see what happens. She said to call and gave me her number. It was 4:30, fuck it, I'll leave 30 mins early and make it up on the laptop later tonight. When I got in my car I called her, she had a really sexy voice, almost passable. "So what do you like?" Standard question, kind of irks me but no way around it.

"On first encounters I can go all the way if the person's right." We talked porn and other kink, when there was a good break in the conversation I said "shall I come over and see if we mesh?" Cheesy, but I like to lay on the chivalric charm.

"You want to play daddy?"

"If you want to be my baby girl, daddy will teach you what he likes." She made a sound between a chuckle and moan in her best high octave girly voice, she said she needed to get ready and to come over in 30 minutes, call before coming up. A quick jaunt to the Rite Aid for some condoms and lube (I cannot fathom how often hosting girls don't have this). Nearly 30 minutes later I drove past her house in a decent neighborhood in San Jose. I parked in an office lot two doors down and got organized, cash, burn phone, car keys (without house keys), condoms, and lube into the pockets. Wallet, work phone, and anything else I don't want to lose gets locked in the glove compartment. When I opened it, I saw a little brown bottle, poppers from a booty call she left. Why not, into the pocket with the other stuff and I dialed her number.

"Just need a few more minutes, come in and have a seat on the couch, I'll be out in a few." Scanning the hood on the way in, I didn't see any red flags. Green grass, late model cars, decent sidewalks, all good signs. Up the stairs (recently swept) of a four unit complex to the second floor and as she said the door was open. I entered and said hello in my nicer voice. "I'll be out in a bit, just have a seat." Inside was a nice bohemian decorated post war until with modern amenities. The decor said straight but artsy, dim mood lighting, I assumed she was a part time dresser. I sat on the couch to watch the porno she had playing on the flat screen.

When she came out I rose to greet her, she carefully walked toward me in her heels, definitely new to exploring her feminine side, daddy it is then. We exchanged smiles and hugged, feeling each other’s bodies out. Danielle was around 40, 5'5, smooth and slim. Passable from the neck down, she did her best with the makeup but practice was needed. The effort put in impressed me and I made the decision to proceed. She offered me a beer and I accepted, she offered some smoke and I took a hit. Soon we were making out. She liked her nipples treated rough and a good spank the ass. For safety I gave her a safe word, "if we go to uncomfortable territory, call me 'Poppa,' if you like what I'm doing all me 'Daddy.'"

"You're experienced aren't you Daddy." I offer a reassuring smile. Then soon she asked for "Daddy's cock." I told her to show Daddy what a good girl like her can do. New to this or not, she had good technique.

I sat down on the couch and had her face me, legs straddled across my lap. I gently peaked in her panties to glimpse her pussy stick and she blushed, putting her fingers over her lips. Inside her panties was a cute little light brown cock with a pink tip, cut, shaved and soft to the touch. "You have a cute clit baby girl, mind if Daddy feels it out." She blushed again but leaned back to give my hands more room. It appeared it wasn't going to get hard for a while and a quick look at her pupils said it probably wouldn't. "You know, totally random, but Daddy has some poppers left over from a party a while back, have you ever tried them?"

Eyes wide and smiling she exclaimed "I love poppers!" I took them out and gave her a wiff. "Mmm, not bad, want to come to the bedroom and try mine?"

Of course I do, I kissed her tenderly and bid her lead the way. From her haphazard makeup table she grabbed a brown vial. You know the type, brown translucent glass, black plastic cap, could contain anything a crazy chemist decided cooking that day. One light wiff proved that her amyls were clearly of a better quality. "Very nice baby, quality like that isn't legal. Let me guess, came over from Tijuana in someone's shoe?"

"Who knows, my friend has them in a shoe box with the Nike logo going the wrong way. Does Daddy like?"

"Indeed, Daddy approves." We took a wiff and kissed. I sat her down on the bed, gave her a wiff and played with her clit while I kissed her from above. She went for my cock again and I gave it to her, she looked up at me with expectant eyes, "Good girl, you service Daddy well."

She moaned and said "I'm Daddy's good girl." I stood there for a while as she sat on the bed and worked my shaft; she was good enough that I had to do some calculations in my head to keep from coming (I find mentally calculating the squares of odd numbers stops any rising orgasm cold). He took a wiff and returned to work, I reached over to the night stand and grabbed my beer. For some reason my mind wandered back to my naive and way under the age of consent days when an older man took advantage of me and I woke up with my first facial.

"Want to try something with Daddy?" I said with my best trust me/mischievous grin. I told her the story of the man and what he did with me. "Think my baby girl is up for it? I'll hold your hand, if you let go I'll stop right away."

She leaned back on the bed and thought about it a minute. I leaned in and kissed her, twisting her nipples a bit, reaching down to her cock which was getting a little hard. "If I let go, you'll stop?" she asked.

"Absolutely, I don't want anything to happen to my girl, use your safe word, or just let go." I kissed her neck, kind reassuring kisses, a firm hand on her hip.
"You are a fan of poppers..."

"Ok Daddy, let's do this, I'm your girl."

"Wonderful sweetheart, grab me one of your hair ties and cotton ball." What happens next is pretty much what happened to the young me with the horny old man, except for the safe word and secondary stop.

"Alright sweetie, lay on the bad, face up and shoulders on the edge of the bed." She lay down, curious but a little on guard, can't blame her, what I described was kinky and a little risky. I took my pants completely off and leaned over her for a quick kiss, "this is where the good girls part ways from the ones who are all talk."

"Show me Daddy, I want to please you." Those words squeezed as much bl**d into my cock as could fit. With my dick and balls where she could see, I wrapped the hair tie around my scrotum, just once, for a loose fit that won't fall off. Then I took the cotton ball, put it on the end of her brown bottle of amyl and gave it a light soaking. I tucked the cotton into the hair tie around my balls but kept my cock from touching it.

"Scoot towards me, so your head hangs back of the bed." She did and I made a few adjustments so her mouth was perfectly in line with her esophagus. I held her hand in mine, "just let go and I'll stop." She nodded while I brushed my cock on her cheek. When she licked her lips I backed up my hips, lined the tip of my dick up with her ruby lips, and slowly slid it in. My cock held in one hand to keep it off the cotton ball and her hand in my other to offer reassurance of a quick stop to this new activity. She looked beautiful on her back; my eyes followed her neckline down past her puffy nipples, to her belly and cute leopard print panties where a tiny bulge twitched. I backed out and eased in, a little deeper each time until I didn't have to guide my cock, her lips providing the course. I squeezed her hand and she squeezed back. I a little deeper and the amyl cotton ball held by the hair tie around my scrotum reached her nose and she got a dose. Her back arched but she held my cock and made a circular motion with her head. I eased out then slowly back in, my scrotum almost toughing her nose. Five more thrusts and she let go of my hand.

I pulled out and held the back of her head for support, she smiled with closed eyes. I gave her a kiss and she put her arms around my neck. After a few seconds she said, "I liked it, but too much, can you get a new cotton ball and use less."

"Sure thing baby girl." Not letting go of her head I reached back to her table and shook another ball out of the bag. "You add it, use what you want." She sat up and puzzled out how to get the right amount on the cotton. I grabbed a baby wipe, took the hair tie and cotton ball of my sack and tossed them. I grabbed another tie and after tying it around my balls she had the new ball ready. "One sec, put your butt under this." I slid one of her larger pillows under her butt and lower back as she got back into position. I gave her a quick kiss and smile then placed the ball back in the tie in front of balls. Without a prompt she arched her head back and opened her mouth, this time grabbing my cock and guiding it in herself. I took her hand and with my free hand started caressing down her cheek. With her hand around my cock she set the pace, I loosened my hips and with her hand around my based she bobbed my cock in an and out. She would go deep on one stroke to get a wiff on the amyl then back me up and work my tip, sucking hard while moving her head in a circular motion. I worked my hands down her neck to her long nipples. I pinched, twisted lightly, messaged a bit. I pulled up on the right one and she took my cock deep, my balls and the amyl cotton right against her face. She gently pushed my hips back and worked the mid shaft, she squeezed my hand. "You like Daddy working your nipples?" A light moan through my cock and a squeeze of my hand. I went to work on the other one, pinch, twist, rub, then pull up. She took her hand off my cock and reached around to my butt, grabbing it firmly. With my free hand I reached for her panties and pulled her little pussy stick out the top. It was almost fully erect now. There was some lube on the night stand I could barely reach, I put a generous dose in my hand and worked her clit, and it sprang up in my hand. Then, with her hand on my ass, she pulled me in deep and held me there for a good ten seconds. I felt her hand in mine weaken and I pulled out, careful to hold her head, I sat on the edge of the bed and rested her head on leg. She looked at me with glazed eyes and smile. "Breather deep breathes sweetie."

She came around with a case of the giggles, rolling her head, smiling, giggling.
"I've passed out on poppers before, but that was so intense, it was like..." she trailed off failing to find the proper analogy. I sat her up and gave her some water, keeping a firm reassuring arm around her mid-section. She nuzzled her face in my neck, shaking off the last of the amyls. More water, a kiss, a hug, put her head back on my shoulder. "Did I do it right Daddy?"

"Indeed by baby girl, you were fantastic, my good girl, taking on Daddy's Popper Challenge." Squeeze kiss.

"One more time, I want to go one more time, you don't have to hold my hand, I'll just push you back when I want to stop." She starts to play with my cock.

"Wait a few minutes babe, breathe the residuals out of your bl**d stream, here come close." I laid her across my lap with my right arm around her shoulder and my left down her panties, while I fiddled with her little brown clit stick I was monitoring her pulse. It was nearly back to normal. I must have hit a nerve in her clit because she moaned and curled up against my chest. I put her lips on one of my nipples and her whole body began relaxing. My mind debated if she could safely do this one more time, last go around she committed to it and took a sustained dose of Tijuana amyl. "Relax sweetie, when your pulse has normalized for a few minutes we can try again."

"But I want Daddy's cock now!" she moved down to suck my cock but I maneuvered her up onto my lap, facing me again. She pouted, lips smeared with red matching the stains on my cock. For a middle aged crossdresser Dani pouted like a valley teen.

Squeezing her hips I pulled her in close, "you’re such a good girl, but Daddy wants you safe. I see your little clit is excited." I rolled her beside me reached down, it was still almost hard, but sensitive enough to make her moan. I put some more lube on my hand and held her firm with my left arm and fiddling her clit with my right hand. Her little joy stock almost fit in the four fingers of my hand. She began to squirm, I could feel the corpus cavernosum swelling, she was on the road to orgasm. "If you hang your shoulders off a little more and use another pillow under your but, Daddy can get naughty with clit while you take him deep" I squeezed her "want that?"

"Mmm, yes...." Her shoulders arched back and her eyes closed, I could tell her mind was focused on her genitals. Snapping out of it she looked me in the eyes, "yes Daddy, give it to me, I want it. You don't have to hold my hand, I get it, what to do."

I pulled her in close for a kiss, grabbed another pillow and with lips still locked began moving her into position. She arched herself right on to the extra pillow and began wiggling over the edge lining herself up. "Hold onto on of butt cheeks, I need some sign your still with me. Is the popper ball still good?" I waved my balls back in forth in front of her face.

"I think it’s good now, right intensity. Oh Daddy, I want it." She settled into the right position and took fold of my cock. It throbbed in her hand reaching full erection. I took her spare hand and planted it on my butt cheek, with the tip entering her mouth she nodded up that she understood what to do. I let my hips go loose, again giving her hand at the base control of depth and cadence. I reached into her wet, lube soaked panties and took her pussy stick and girly balls between my thumb and forefinger. As I squeezed I used the fingers on my other hand to rub the dorsal artery and nerve. Dani's little joy stick was as hard as it had been all night, still soft, but pulsing and warm. I adjusted my grip with my left and so the index and forefinger where just around the base of her clit and worked the four fingers of my right hand on the shaft while there was enough lube for my thumb to rub the head. Then I became suddenly aware of the orgasmic sensation coming from cock. Dani had worked herself into an incredibly rhythm where she would take me deep, get a wiff of amyl, then move here head in a circular motion up the shaft, shake her head a few times, then go deep again. She never broke suction and I never felt a tooth. Closing my eyes I enjoyed her cyclic technic, made a mental picture, and then returned to her hot little clit. I added a twisting motion to my right hand and felt her whole member throb and pulse. She made grunting moan as I felt her legs tense. Her little clit popped once, more grunts, she added her other hand to me ass cheeks and pulled me down her throat, to the balls where the amyl cotton lodged next to her nose. Another spew of her white funk flew high by my face, her shaft still throbbing I stroked faster. She had both of my ass cheeks in a death grid, my cock well past her tonsils. With the another throb of her clit about a teaspoon of white shot out and onto her belly. Finally, with a final tense of her torso and legs, her watery last bit of cum oozed up, out and over my hand. Her hands dropped and I felt her go limp.

Worried I held her head, whipped my cock out and looked at her face. With glazed eyes and a barely lucent mind she said "oh my god...." I maneuvered her sideways so her head rested in my lap, with my hand on her chest feeling her heart beat, which wasn't as fast as last time. "Oh my god..." she repeated, regaining control of her hands, or remembering she had them, she wove them lazily around until they found an arm or should of mine they could rest on. "Oh my god..." again, she stared up at the ceiling like it was a hundred miles away. She praised god two more times, twitched a bit with post orgasmic aftershocks, then promptly fell into REM sl**p in my arms. I held her for a while making sure her breathing and pulse were solid, gently I laid her head on a pillow and went to the kitchen to help myself to another beer, still hard cock swinging back and forth. I drank the beer in the bathroom while I washed up, cold water beating back my erection enough to put underwear back on. After my pants went on I could hear Dani's contented moaning in the bedroom. I grabbed my shirt and walked in, with a smile I sat down next to her. "You’re going Daddy?"

"Yes sweetie, I've got work to finish up, you played hard, Daddy's proud. Lots of girl's are all talk on the internet then flinch when the time comes. But not you baby girl, you went all the way." There was that blush again, the shy look away. "But Daddy didn't cum,” shook my head feigning sternness. Her mouth opened a little but no words formed. "Don't worry baby girl, Daddy is going to come back and claim that ass of yours for his, you will feel this cock for days. You going to serve me when I come back? Give that cute ass up, ride Daddy and suck him till your cute little mouth is full?"

"Yes Daddy, please, I'm your good girl, I want to make you happy."

"Yes you are my sweet girl" I kissed her on the check and locked the door behind me. And I did go back and take her in every way I could think of. She's such a good girl.

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