The Young Crossdresser Part 2
So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful.
mega orgasm
I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group.
I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass.
Now I was 15 and one weekend my parents went away with some friends and I knew that this would be the perfect oppurtunity to fulfill my strongest urge and desire to be fucked completely by a man.
Friday evening arrives and my parents head out for their trip and I waste no time in getting dressed up.
Tonight I was not going to fuck mom's dildo's but I was going to find the real thing.
I put on a pair of satin purple polka dot string bikini panties a purple bra,black thigh highs and garter,black mini skirt and black blouse,I stuffed my bra with water filled balloons to give me some tits,black heels and a brunette wig,applied my make up and found the keys to the car left sitting in the driveway.
I took one last glance in the mirror and got in the car and drove away.
I didn't care that I had no license,I was only going about two miles down the road to mom and dad's adult bookstore where I knew I would find some to fuck me.
I arrive at the store and park. Once inside I got over to the counter and give Bob,who know's me as the boy but not as the "girl",a five dollar bill and ask for tokens to go into the back where the video booth's were.
He doesn't even bat an eye,just hands me the token's and goes back to reading his book.
My heels make a loud noise as I walk through the halls of the booths looking for an empty one.
A few guys hanging around outside of the booth's grab me and grab my ass as I walk by them.
I continue walking until I find an empty booth near the back,I go in and drop my tokens and find a hot she male movie to play.
It doesn't take but two seconds for a cock to come through the glory hole.I drop to my knees and suck it for all it's worth. In moments he is spewing his hot creamy load across my tongue and down my throat. I milk it for every last drop and he pulls away.
two or three minutes later another cock is poking through the hole,nice and thick. I take him in my mouth ,his salty precum wetting my tongue,he taste good.
I suck this nice peice of meat for 10 minutes when he lets loose with what seemed like a gallon of cum deep into my throat,and being the good girl I am I swallow it all.
Now I am horny as hell and need to find someone to fuck,I leave the booth and scan the hallway's for a potential lover.
I notice near a back corner,an older man 60ish,standing there,rubing his cock through his pants as he stares at me,he looks like a business man of sorts.
I walk over to him,and as I approach,he pulls out a very nice cock,fat and not too long,but very hot looking.
I walk over to him,grab his cock and whisper in his ear, "I want you to fuck me".
He replies "where?"
I tell him "there's a room in the back,I have a key for,it has a bed,porno and anything else you might want."
He ask's me how I know about this and I tell him my parents own the store.
I tell him no one ever comes back here,only my parent's when they meet someone here.
So I lead him into the back room,pretty small space,just big enough for the mattress the was on the floor.
We go in and lock the door behind us. He ask's me if I have ever been fucked before,and I tell him sorta,that it was very tight and the guy came almost immediately.
He then say's "oh...you have a tight pussy huh?"
I smile and say "yeah something like that."
I help him take off his clothes and go down on my knees and start sucking his hard cock,rubing my cock through my panties as I take him in my mouth as deep as I can,gagging a few times.
After a few minutes,he pulls me up and put's his hand on my "pussy" and let's out an "OH I thought you were a girl"
I said "Tonight I am".
His smile gets bigger as he rubs my cock through my panties and he ask's how old I am,I tell him 15 and the smile gets even bigger.
"Mmmmmm...a hot young sexy girl looking to get fucked...I like that!"
He ask's me if I'm ready and I say "I've wanted this for a long time,yes I am ready!"
He pulls my skirt off and says he want's to fuck me with my panties on and this turn's me on soo much. I always wanted to be fucked while wearing my panties.
I root around the nightstand next to the mattress and find some KY lube and hand it to him. I lay down on my back on the cum staind mattress.
He slides my panties to one side and spreads some lube on my awaiting ass,my cock straining in my wet precum panties.
He takes and works one finger into me,then two and he slowly fuck's me with his fingers.Getting me nice and ready to accept his thick hard cock. Once he has three fingers in me ,he tells me I'm ready. Just relax I tell he I'm way beyond relaxed.
He takes and puts some lube on his massive meat and slowly slides it into my ass.
The feeling is incredible comapred to my mom's dildo's. As his balls hit my ass,I start cumming in my panties,soaking them all the way through.
He takes a pillow and slips it under my ass to make it easier for him to fuck me. My legs slightly bent and up in the air. His hands caressing my stocking covered legs as he starts to pump in and out of me slowly.
My fake tit's swaying up and down ever so slightly. His cock feels amazing in me. I moan soflty as he continues to pump me slowly.
After about fifteen minutes he quickens his pace,my legs swaying back and forth as he continues to rub the stockings covering them. Telling me how hot I am,that his wife never dresses this way for him.
I slide my cock out from underneath my purple silky,wet panties and start stroking as he fucks my virgin ass and I soon start cumming again,shooting another big load all over me.
He pulls out,scoops up my cum and puts it all over his cock and slides it back into me,fucking harder now.
Our moans getting louder and our breathing heavier.
He then pushes my stocking covered legs all the way back,pinning them by my head,and now he is fucking me like I always wanted,hard and fast.
Soon his eyes close and and he has one last hard pump and I feel his cock expand in my ass as he dumps his hot creamy load into me. His grunts and moans are really loud as he let's go of spurt after spurt of hot,white creamy cum.
I moan loudly too,as it is incredible to feel this man dump his load into me.
He stops sliding his cock in and out of me he finishes cumming,my lags still behind my ears. I slowly gyrate my hips as his cock grows limp inside of me. He pulls out,lights a cigarette and tells me how great I was.
We make small talk for a few minutes,I tell him I will be here every night until Tuesday when my folks get back home. I then tell him he should leave first and then I will come out a few minutes later,as to not raise any suspicions.
As he leaves the room,I glance out the door and see no one standing around,so I know we are safe.
I straighten up my panties and put my skirt back on and start to head out of the room 15 minutes later,his cum dripping out of me and into my panties.
Before I go home,I need one more cock to suck. As I walk past the booth's,a door opens and a man,in his 30's maybe grabs me and pulls me in.
He is all over me,kissing me,rubing his hands up and down my body. Tells me he saw me go into the back room and heard everything through the door.
Without hesitation,he picks me up and puts me against the wall,slides my wet panties down and slips his cock into my already well fucked ass and starts fucking me like crazy. Saying "is this how you like baby?","you're such a dirty whore aren't you?" all I could do was say "YES!!!!".
My ass squishing with every thrust ,my previous lover's cum being forced out of me by his hard pounding.
It only takes him no more than ten minutes when he shoots his load into my well worn ass.
We both see a cock poke through the hole,he lets me down and forces my head down and tells me to "suck it..suck it dry".
No problem there. He forces my head up and down on this strangers cock and soon he is exploding in my mouth,I am told to swallow every bit of it.
Again ,no problem. Once the stranger's cock is gone,he pulls me up and hugs me,and say's "I hope I didn't frighten you". I tell him absolutely not,that I am a horny little slut and that how we should be treated.
He says "Thank You" and leaves the booth.
I compose myself and head out to the front of the store to leave,and on my way out Bob says "looks like someone had fun tonight". I just smiled and walked out the door,if he only knew...maybe he did,I don't know.
Phyllis, The Litte Redhead, episode 7
Dot was crazy about the cute and shy little redhead
We met Frank in 1969 when he was married to Phyllis. He was discharged from the US Air Force at the desert base near Apple Valley, out in the Mojave Desert. That's where he met her and decided to settle. This was my first stateside assignment after my tour in Vietnam. My wife was quartered at the air base during that year. Dot was a very outgoing person and made friends quickly at every new duty location. The women, especially, liked her. I was always interested in her budding friendships, of course, and she kept me updated by mail. I had a lot of mail.
Frank and Phyllis were part of a camping group my wife Dot made friends with. We became especially close to them because Dot was crazy about the cute and shy little redhead. She was almost five feet tall and tiny but her figure was proportionate. It was perfect, in fact, but small. Dot liked to joke around with her, calling the diminutive redhead her little baby girl. Dot would lift her easily, hugged and kissed her like a small child. Dot on the other hand was almost of six feet, long-legged, a beautiful blond with an ass to match.
We partied a lot with them and many occasions dined and danced till daybreak. Camping trips in the desert were a riot. Sometimes we went with a large group and other times we camped with Frank and Phyllis in their motor home. Camping always started with a bloody mary for breakfast and the bar was open the rest of the day. Many cool desert evenings were spent out under the stars sitting around the campfire enjoying our cocktails and smokes as usual. One such evening, Dot lay comfortable on a mat and sleeping bag with Phyllis snuggled up to her to keep warm. She had begun to return Dot's affection for her lately, and I think she might have been vaguely aware of Dot's intentions.
We were all in a haze around the campfire that dark desert evening. Frank and I were engaged in conversation but very aware of the girls on the mat. Frank was a really nice guy and he had an idea of what Dot was like from Phyllis. I knew he was interested in Dot since she was just as friendly and affectionate with him as she was with his wife. I watched Dot dance with Frank on many occasions and he thoroughly enjoyed the cock teasing she gave him. She told me, with a gleam in her eye, that Frank had a huge cock and that she fondled his erections whenever they danced. She said she wanted some of that and told Frank as much, but he would have to wait for his wife to approve. Frank wanted to fuck my wife. He knew that his patience would be rewarded. Dot concentrated her attention on her little redhead mostly and he looked on in great anticipation. Dot and Phyllis were also engaged in conversation and soon began to feel the chill in the air.
"Come on baby, let's get into the sleeping bag, it'll be more comfortable," Dot said to Phyllis. Giggling and tipsy, Phyllis eagerly agreed. They settled into the bag and got comfortable resting their heads on their arms facing each other. Their conversation continued but soon toned down to inaudible whispers. Dot, idly stroked Phyllis with her free hand then pulled the bag over them and continued the stroking underneath. The whispering stopped. The movement in the sleeping bag did not. Frank and I lit up a joint and kept an eye on the sleeping bag. I saw Frank, sitting across the fire from me spread his legs and adjusted the growth in his pants. Suddenly, the little redhead sat up.
"Frank, honey, would you fix another tequila sunrise for me? And pass that doobie while you're at it." Dot, still l in the bag adjusted her clothing. In the light of the fire I could see the motion of her hands between her legs. Frank saw it too as he moved to fetch his wife another drink. Phyllis took a couple of hits off the joint while Frank went into the motor home. She gave it back to him when he returned. She took hold of his hand and pulled him down to her, pursing her lips for a kiss. She then whispered something in his ear and he nodded in return. Frank, smiling at me, sat down again. We both watched her as she finished off her drink and turned to Dot.
"Move over, babe." She scooted back into the bag with my wife. Dot pulled her close and she resumed her caresses. Phyllis first began moaning softly. Then her breath came rapidly. The little redhead climbed on top of Dot and was soon kissing her about the face and neck. Because of their difference in size Phyllis it was an easy reach for Dot's hands when she cupped the redhead's ass with both hands. Phyllis began humping my wife's belly button. Only their heads were visible but we could see that their lips were now locked in open mouth kissing. I don't know if Phyllis had any experience with other women before, but she was thoroughly enjoying the moment and I knew she was loving Dot's fingers.
Dot told me later that she began to fondle the redhead's ass, then pulled her panty down and then worked her fingers down her crack into the folds of her pussy. Phyllis spread her legs and straddled Dot at the waist. When the redhead was wet Dot inserted two fingers into her from behind then reached underneath with her other hand to find the redhead's clitoris. Phyllis began making small animal noises breathing ever more rapidly into Dot's mouth. Phyllis broke the lip lock and disappeared into the sleeping bag leaving Dot looking surprised at Frank and me. The little one, Dot said, released my wife's breasts from her clothing and took a nipple in her mouth while fondling the other. Dot turned her head to smile at us and licked her lips. Phyllis had a whimpering, grunting orgasm. When it subsided, she poked her head out from the sleeping bag and looked to see if Frank and I were still there. She smiled sheepishly.
"Let's go in the motor home, babe." When they disentangled and emerged from the sleeping bag, Dot's top and the redhead's bottom clothing were missing. I saw in the firelight that she was indeed a true redhead. I hadn't noticed till then, but Frank had exposed and was stroking his enormous hard-on. The women paused to admire Frank's cock. Phyllis held it and pumped it with her small hand. "Come here, Dot. Feel it." Dot grinned at me as she fondled it. She bent down and I thought she was going to go down on him right then and there, but she just kissed his mouth and hurried after Phyllis. Dot's nipples gleamed wet as they made their way past the campfire, laughing, arm in arm into the RV.
"Wow! Was that something or what? She asked me if I would mind if she fooled around with Dot," Frank said.
I replied, "I thought it was something like that and I guess my wife told Phyllis that I was cool with that. By the way, that's some tool you have there, buddy." My fat eight inches was nowhere near his size. It was a good ten inches long with at least a three inch girth. "How do you get that thing into her?
"It's a little difficult and I have to wait till she's really wet and use lube," he said still stroking it. "Most of the time she gets on top and takes as much as she can accommodate, but I've never really buried it to the hilt."
"I think you can look forward to that tonight," I told him. "I've seen Dot take a couple of huge ones." He looked at me like he'd just won the lottery. We heard the girls using the small shower in the motor home and we anxiously waited to see what was coming next. Or should I say, who was cumming next. We waited till they had time to get comfortable then went into the RV. It was darkened except for a small light in the hallway. They must have felt us come in but didn't let that disturb them. When our eyes became adjusted to the light we saw that Dot had the redhead on her back with her small legs wrapped around her shoulders. Dot knelt on the floor next to the bed and was noisily eating the redhead's cunt. Phyllis was writhing and twisting, her hands firmly grasping Dot's head to her pussy.
Phyllis glanced up at us standing in the doorway, but she was looking right through us. It was like a blank stare. Breathing hard, she was totally lost in lusty pleasure. Dot's beautiful ass shone beautifully before us. We saw her fingers flicking between her thighs. Frank looked at me and I tilted my head toward Dot. He quickly undressed and knelt behind Dot. Feeling him behind her my wife reached back with the hand that was in her crotch and felt for Frank's salami. When she found it she grasped it firmly in her slender fingers. She hummed into, then broke the suction from the redhead's cunt and looked back at Frank.
"Oh, fuck yes! Give me that meat, Frank!" He inched into my wife's bare pussy. I watched closely as he brought his enormous cock to Dot's pussy lips and rubed it up and down her wet slit till he found her hole. I wanted to reach over and help him. I placed my hand on my wife's ass and slid my fingers down past her crack. Down further I spread my fingers to allow Frank's cock between then. With my thumb and index finger I encircled it and squeezed. I didn't look up at Frank, but there was no protest so I didn't stop. I grasped it firmly and placed it to Dot's nether lips. Her labia spread to allow Frank in. I rubed her cunt with Frank's cock head and fit it into her. Her pussy was wide open and I smelled the warm aroma it exuded. I've seen my wife this horny when her pussy is wide and hot. I placed Frank's cock there and tugged it forward into Dot.
Then I looked up at him and he said, "I've been waiting a long time for this." Little by little, inch by inch, he pushed gently. My wife's labia disappeared as he pushed in and then extended out and around his cock when he pulled back. He had it half way in then stopped. My wife's pussy was swollen and flushed around his cock and I felt around her engorged labia stretched around it. I wondered what it would be like to suck it. I leasned down to lick at my wife's labia and his cock as it slid slowly in and out of her.
"Give it to me, Frank! Give it to me!"
"It's big, Dot. Take it slow," Phyllis said as she turned to look for me. The pleading look on her face as she watched me stroke my cock made the message clear. I knelt on the edge of the bed next to her and she reached for my cock. She rubed the precum around in her fingers then brought them back to her lips. She opened her mouth and pulled me to her. I brought my knee over her head and began to fuck her mouth. There we were. Frank fucking Dot, my wife eating her little redheaded friend, who in turn was sucking my dick. Frank watched his wife while taking long strokes into Dot. Dot hummed a tune into Phyllis and humped back into Frank. He fucked faster and deeper with each stroke till he finally had it buried completely. He held it there and ground his pelvis into my wife's ass with a guttural sound. Dot could not hold back her orgasm as she usually likes to do. She removed her mouth from Phyllis to release her throaty scream.
"Oh! Oh! Oh, fuck Frank! Fuck meeeeeeeeee! Ted, baby, he's making me cum! I'm cum-cumming now!" Phyllis popped my dick from her mouth while my wife was busy getting porked. She swung her small outspread legs to me. They quickly wrapped around my waist. No preliminaries were necessary. I inserted my smaller but adequate penis into her quickly and fucked for all I was worth. I was pounding her pelvis with mine and she was enjoying a good hard fuck like she wasn't able to do comfortably with Frank. We came together, her arms, legs, and mouth firmly attached to me. After Dot and Frank had their orgasms, my wife sat on the edge of the bed and took Frank's huge and still hard cock in her fingers and stroked, licked, sucked to her heart's content while Phyllis watched in amusement.
"Nice, isn't it, Dot? Did you manage to get it all in? I never could get a good hard fuck with it."
"Yeah, but I think I'm going to be a little sore tomorrow," Dot replied. "Why don't you come over here and soothe it for me?" It had been a while since my wife had another woman's mouth on her pussy.
Phyllis hesitated a moment, then said, "What do you want me to do?" Pretending she was annoyed, Dot said to her, "I want you to suck your husband's cum out of me, baby!"
Now the redhead was smiling. As Dot lay back flat on the bed she pulled Frank's cock with her, Phyllis made herself comfortable between my wife's outspread legs. First she gingerly placed her small hand against Dot's pussy and made small circles.
"I've never done this before," she said, almost to herself. Frank's prick was in Dot's mouth but his eyes were on his wife. This was a new experience for him watching his wife playing with another woman's private parts.
"Have you ever thought about it," I asked her as I leaned back against the headboard to light a cigarette and watch.
"I have fantasized about having sex with another woman, but I've never had the opportunity or met anyone I wanted to seriously consider it with. I thought about you, Dot while I masturbated a few times," she coyly admitted. "You always make me horny when I'm around you," she said to Dot. Frank leaned over and they kissed as he held the back of her head. He then gently pushed her head toward Dot's waiting pussy. Phyllis cautiously licked at it.
"Ummmm, I can taste Frank too," she said and went to it with open mouth.
"Yeah, baby girl, do it, but be careful with the fingers, my pussy is tender."
Phyllis quickly found she really liked eating pussy....often. There followed many good times with Frank and Phyllis. Fortunately, we were destined to reunite with our old friends including Frank who had in the meantime divorced Phyllis and found Maxine, another episode. The redhead had run off with the mailman who was evidently a more comfortable fuck than Frank.
Continue reading Dot And Our Neighbor Jan, episode 8