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CRISSY

The summer after high school I moved into this cheap hotel downtown. I’d been working in the mailroom for a large company, and really needed to get my own place, but I didn’t have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I had one large room, with a small bathroom, and a tiny kitchen. It was the cheapest one they had. After work I’d dress up and watch tv, then sleep in my little black nitey. A couple weeks after I started living downtown, I ordered a vibrator in the mail, it quickly became my favorite toy. By the beginning of summer I had fallen into a steady routine of coming home from work, dressing up, having something to eat, then masterbating myself to sleep. I went through a lot of batteries, falling asleep with the vibe buried in my virgin sissyhole. I had also got a few really sexy outfits, and a great pair of clunky heels.

I became a little daring after awhile, there was a trash room down the hall. I started to take out the trash dressed up. I’d leave my door open, then dart down the hall and back. It probably didn’t take more then two minutes, but it really got my heart beating. One night I was coming out of the trash room, I was startled to see an older black man, about 30 standing in an open doorway. I froze the minute I saw him. He smiled and asked if I wanted to come inside and smoke a joint. Startled, I mumbled “no not now,” and fled back to my room. I heard him say “stop by sometime cutie, just knock.” My heart was pounding when I made it back to my room. I sat down, wondering what to do. Did he know I wasn’t a real girl? Did he want sex? Should I give him sex? Would I want to suck him? Fuck him? Should I go back? What if I got ****d? What if he and a bunch of his friends ****d me? I couldn’t sleep a wink all night. I was a mess the next day at work, wondering what I should do. The more I thought about it, the more tempting it became. After all the hotel was on the seedy side, there were a number of residents that looked kind of shady. Pretty much everyone seemed to mind their own business.

That night, after shaving my legs, so they were smooth and sexy, I carefully painted my nails a fiery. I dressed up in my sexiest outfit. A blue skirt, that came down to just a little above my knees. A tight blue and white sweater. Underneath I wore a white bra, 34b, stuffed with some old nylons, white bikini panties, and pantyhose. Of course I had my clunky shoes on. I put on a pair of clip on dangly earrings, and a little heart necklace. I took my purse with my keys, some lipstick and makeup, and a few dollars. Working up my courage, I left a little earlier then usual. I must have stood outside his door for five minutes before I actually knocked. He wasn’t there, my heart sank. I must have went back a dozen times, before I gave up. Filled with disappointment I sat in my room. I thought, I can leave a note! Carefully I started writing one. After a few tried, I finally settled on, “stopped by to see you, I’ll try again tomorrow night.” When it came time to sign my name, I paused, I couldn’t give him my actual name. I needed a girl name. “Crissy, that’s a good one,” I thought. So I signed it that way, with a little heart over the “I”. I slipped out of my room and slid it under his door.


The next day seemed to drag by. Finally I went home and changed, repeating the same process as the night before. I again stood before his door. Timidly I knocked. The door quickly opened. Before me stood the man from two nights ago. He smiled, “Hi Crissy, come in cutie, my name is Charles, but my friends call me Hollywood.” Hesitantly I entered, trying to remain as calm as I possibly could. No one had seen me like this, except this guy. Hollywood? What kind of name was that? Swaying in my heels I found my way towards the couch. “Sit down, want something to drink?” “Y-y-yes, p-p-please” I managed to say. I sat at the edge of the couch, trying to primly keep my knees together, as I tugged my skirt down.

Bringing in two glasses, along with a bottle of beer, and a bottle of Pink Champale, Hollywood sat down on the couch, near me, but not too close. Nervously I took the glass, and slowly took a sip. Talking as he rolled a joint, he asked, “How long you lived here? “About s-s-six w-weeks.” “Mellow out girl, I ain’t gonna hurt you, just wanna get to know you.” “Been dressing up long?” So he knew, “as long as I can remember” I said, pretty much telling the truth, but still scared to death, but glad at least I didn’t have to awkwardly explain later. Lighting the joint Hollywood took a couple long drags, then handed it to me. Daintily I took a small toke, then started coughing, not having smoked it too often. Handing the joint back, I drank more from the glass. Passing the joint back to me, I took a couple tokes, not coughing this time. As we smoked, and talked I started to feel a little more at ease. Finishing the joint and the Champale at about the same time, Hollywood brought me another bottle. After filling my glass Hollywood rolled another joint. As we finished the second joint I started to feel really fine. Hollywood moved a little closer, and put his arm around me. I snuggled up to him and sipped my glass. Running his fingers through my hair, he said “I really like you Crissy, you’re really a pretty girl.” I could feel myself starting to get aroused.

Turning my head, he pulled me close and kissed me. Hesitantly I kissed him back. Opening my lips, his tongue slithered into my mouth. Slowly I started sucking his tongue. With one hand on the back of my head, and the other, wrapped around my waist, I was powerless to resist. His hand slowly slid down my side, lightly caressing my knee. I put my hands around him, kissing him back, sucking his tongue into my mouth. My arousal was overcoming my fears. My mind was racing, here I was kissing some guy I just met, dressed up like a typical teenage girl. It was almost like a dream, I felt just like a girl out on a date, making out a little. Gently he pushed me back on the couch, his kisses taking my breath away. His hands slowly sliding up my leg, slowly up, undr the hem of my skirt. Politely I took his hand away, once, twice, three times, but it always returned after a couple more kisses. Each time, letting him get a little further. His fingers slowly flicking across my crotch. Starting to moan softly, as he sat back, taking a swig off his bottle of beer. Breathlessly I sat up and tried to compose my self a little as I drank down my glass of Champale. Hollywood asked if I wanted another, “Yes please” I said as I straightened myself up.

Taking the glass, I drank a little more before sitting it down. Hollywood sat close by. Kissing me again he took my hand. Placing it on his swollen crotch, I froze. Knowing what comes next I squeezed him through his tight polyester pants. Kissing me, whispering how pretty I am, telling me how much I was turning him on. Forcing myself to say “I-I=I’m a v-v-ir-gin. I.ve never done anything like this.” He whispered back, “I’ll go slow Crissy,” as he slowly pushed my head down. I wasn’t sure if I really wanted to do this, but I didn’t resist. Instead I was on my side, kissing the lump in his pants as he undid his belt. Taking my hand, he placed it on the snaps on top of his pants. I took a long pause, before unsnapping his pants and slowly pulling the zipper down.

Reaching in, I grasped him through his underwear. Slowly I ran my hand up and down his shaft. He wasn’t too big, about six inches, but he was thick. Hollywood leaned back in the couch, sipping his beer as I slid my hand into his underwear. I lightly squeezed him as I slowly started to jack him. My head rested on his lap as I pulled his thick dick from his pants. I watched from inches away as I slowly jacked him. After a couple minutes, I felt his hand gently against the back of my headed, pushing me closer. Hesitantly I kissed the top, flicking my tongue on it. The hand pushed down a little harder, slowly I parted my lips, as his meat entered my mouth. Working the head inside, I took as much as I could, before slowly sliding my lips back up the shaft. I worked my lips slowly up and down a few times, somewhat shocked that I was really giving a blowjob.

Letting him slip from my lips, I slid to the floor, positioning myself on my knees in front of him. Looking up as I took him back into my mouth. Slowly I worked my lips up and down on his dick. Hollywood laid back, giving me encouragement, “that’s it Crissy, take your time,” as his hand pushed against the back of my head. I sucked him for about five or six minutes, then he moaned, sending spurt after spurt of cum into my mouth. I swallowed as much as I could, the rest dribbling off my chin. He smiled as I looked up into his eyes. “Good girl Crissy, we’re going to have lots of fun.

We spent the night together, snuggled together in his bed. He rubbed my crotch, making me fill my panties with cum just before we dozed off. Before I left in the morning, I gave him another blowjob, then left for the day.

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The morning after Paula had called with the terrible news, I was hung over, sleep deprived and deeply depressed. The flight to Seattle and then to Eugene had to be the worst I ever experienced. Sandy stayed up with me the night before sharing drinks, listening to Vy's and other punk rock music and listening to my reminiscences until she passed out. At the time between steady girlfriends, even if I had one, it would have been Sandy I would choose to comfort me or share the burden of my pain....

2 years ago
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The Half LilinChapter 9

It was a demon! A demon was sitting with her legs stretched out on my couch, watching a rerun of The Simpsons on my tube! A demon that looked just like me, save that her wings were more reddish in colour and her horns curved down and forward instead of swirling to the sides like mine. She also had hair that appeared to be long and blonde, unlike mine, not to mention the fact she was also smaller than me, and—sad as I was to admit it—cuter than me in my lilin form... I was staring agape from...

4 years ago
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The Most Wonderful Punishment

Hey ISS readers! I am Sanjay and I stay in Chennai. I am 19 years old and I am gay. I am a fat round guy and I have big butts and boobs too. I have a fetish for clothing. I always have felt horny when I see men wearing lungi and walking on the road. I also feel aroused when I see men pissing on the road wearing lungi. This lungi fetish of mine drove me to great experiences. I myself do not own a lungi because I’m too shy to wear one in front of my house people. But this extreme affinity to this...

Gay Male
3 years ago
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Face to Face

The party was just beginning to wind down. This was the first time that most of these people met face to face, instead of video chatting over Discord or Skype. Everyone knew each other, which was a saving grace, but when you are introduced to a live person, a person you may have talked to through the miracle of the internet with, the game changes a bit, and anxiety sets in.This was never the case for Thomas, or Mac1800 as his online friends knew him. He was always the life of every group call...

1 year ago
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Do you REALLY want to be broken

The following is my response to a Craigslist ad. The secret sissy in question claimed to be a young, successful man, heading his own department at work and living the good life. But he yearned for his teen years, where he would passably dress up and meet men off the internet. He wanted to be completely broken and feminized to the point of no return. Here is what I had to say, and after writing the little scenario at the end I thought it might be a good enough start for my first...

3 years ago
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Hot Sex With My Favorite School Teacher

Hi ISS story readers. I am Akhil and I am a daily reader of ISS. Today I am going to tell you all about my sex experience with my school teacher. I am very much interested in boobs and any housewife who is unhappy can contact me as I can make you happy. Coming to the story, the name of the teacher is Sangeetha who is a Maths teacher in our school. When I was in 12 class she has joined our school and came to teach Maths. She used to wear a transparent blouse where her bra was visible. She looks...

1 year ago
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Return To Pleasant Street Ch 05

DEBBIE’S ALL GROWN UP Larry Tilton lives three doors down from me on the East side of Pleasant Street. Larry has been divorced for about three years, now. He and his ex-wife were married for eight years, and have a couple of wonderful kids. The marriage came apart because Larry’s ex-wife, Monica, developed a drinking problem. That led to Larry having a short affair with Debbie Lawrence, a cute neighborhood girl who babysat for them. I’ll give him credit, he broke off the affair in an effort...

1 year ago
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GirlsWay Quinn Wilde Monique Alexander Love And Hate

Monique Alexander is on the phone with her lawyer yelling at the top of her lungs. She’s about to lose her company to her business partner who is suing her for everything. When her lawyer reminds her that they need some evidence, Monique has just about had it with his incompetence. She needs results and needs them now! While she’s on the phone with him, her business partner Quinn Wilde walks in the room. She yells at her lawyer and hangs up the phone. When Monique demands to know...

xmoviesforyou
4 years ago
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Big Brothers Little Woman

Adriana felt the delicious touch of her boyfriend Jeremy's hand under her top. This was her chance to finally be able to lose her virginity to one of the hottest guys in school. Adriana was 16 and felt so ready to be able to let loose. This was a perfect opportunity as well since her parents were not home that afternoon. She'd skipped her last two classes to bring Jeremy home with her. "Mmm baby, you smell so good! I can't wait to be inside of you," Jeremy exclaimed kissing her...

2 years ago
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Maa Chudi Gair Mardo Se 8211 Part 7

Namaste mitro. Aap sabne is kahani ke pichle bhag pehle padhe uske liye aap sabka bahut bahut dhanyavad. Ab main aage ka bat aap sab ko batane jaa raha hu. Dadaji aage aake let gaye meri mummy ne apne tang ko hawa mein utha ke faila diya. Dadaji ne kaha, “Bistar ko pakad lo hath piche karke.” Meri mummy ne dadaji ke hukum ka palan karte hue bed ko piche se pakad liya. Ab dadaji apna muh meri mummy ke fuddiya ke pass le gaye aur sunghne lage. Aur dadaji dhire dhire saans lete hue mummy ki...

1 year ago
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ChameleonChapter 1

Yeah, I'm a jerk. I always have been a jerk. And I was destined to remain a jerk for the rest of my life. Then I got lucky. This is the story of how that happened. You need some background to understand how I got this way. I am a 16-year-old high school dropout-to-be named Josh Logan. I stand 6 feet-2 inches tall in my socks, when I have socks to wear and I weigh 185 pounds, none of it fat; if fact, I can't remember when I ever had any fat. My hair is long because my mom is rarely sober...

1 year ago
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Blacked Carolina Sweets Rich Girl Desires Part 2

For as long as she can remember, Carolyn’s friend has always had everything she wanted materialistically. But when her friend manages to take advantage of their private tutor, it’s the last straw. She knows that Carolyn has always had a thing for him, and now it’s her turn for revenge. After inviting him over for a private session, she makes sure that she is dressed to impress. Once they have eaten a nice meal that she has specially cooked, she asks whether he wants dessert. No prizes for...

xmoviesforyou
2 years ago
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Ryan comes to surprise

Completely fictional, names made up Ryan had just pulled up in the driveway when he saw his twenty-eight year old neighbor washing her car in her driveway. She had just moved in eight years ago and he was now a junior in college. They got along good, when he was younger she would sometimes ask him to rake the leaves in her yard for some cash or clean the gutters. Once during summer he had accidentally seen her change into her bikini while he cleaned out the gutters. Although, she said it...

4 years ago
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Tag Team

(I wrote this story with Odink. This is a 50/50 collaboration. Thank you, Odink. Your input was sensational!) Kim's phone rang early that morning. She looked at the caller ID and noticed it was JD. With a groan, she picked up the receiver. “I know that you are my best friend, but prepare for an ass whipping. Do you realize it is 7 am?” she grumbled. “Yes, and you need to get your lazy ass out of bed. I reserved us a spot at the lake, but we need to get there early. So, get up and get to...

Group Sex
3 years ago
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Coffin Duty

COFFIN DUTY(A Sequel Of Sorts For A New Haunt)T.S. FESSELNDisclaimer: This is a work of amatory fantasy. Any resemblance to people living or dead is purely coincidental. If you are under the age of 18, please stop reading here. If you are a bit squeamish about graphic depictions of sex and bondage, please stop reading here. The author takes no responsibility for those who wish to reenact anything written below.Permission is granted for private use. The author wishes any agencies that wish to...

2 years ago
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Teresa 1 She Begged For It

TERESA, 1SHE BEGGED FOR IT,This Story Is True,, Starts Slow,, Ends Nasty… I used to go to a bar/steakhouse called MARMAC’S. I knew the band, (good music) and I would go there after work to dance & unwind. The joke at the place was the name M,A,R,M,A,C,'S stood for Middle Aged Raunchy Men After Casual Sex. I worked swing shift so it was perfect for me. I still got to party and it kept the party under control. There was this one woman who’s name was Teresa. She had blonde hair, big...

1 year ago
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Bhai Se Chudi

Hi indian sex stories dot net doston , me shweta from ahmedabad. . .Meri figure 34-32-34 hai…School me thi tab ek ladke ne muje propose kiya to mene us time to use reject kiya or next day rakhi bandh di…Usne b sry bola aur fir hamare bich me bhai behn ka relationship continue hua…School ke bad hamara admission alag alag college me hua par vo aksar meri college aata rehta… Vaha meri ek friend thi pooja usko vo bahot pasand aayi thi aur dhire dhire pooja b use like karne lagi aur dono ka...

4 years ago
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A Sister With A Dragon8217s Flame 8211 Part II

Hello and lots of love to all the amazing readers of ISS, I want to firstly say a big thank you to all the wonderful users who read my first true story and just fell in love with it, you motivated me to share more of myself with you, and thought of all the guys and girls here playing with their cocks and clits to my words really captivated me, a few people had the same experience as me, it was eye opening, so please get in touch, This next Chapter is dedicated to all of you, and if you already...

Incest
1 year ago
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A Broader Palette The Conclusion

A Broader Palette By Becky [email protected] geocities.com/beckymagi Chapter 6: A Clean Slate "You didn't really think I was cheating on you, did you Jim?" Stacy asked as she hung up her coat. "Brendan's been such a mess since his parents died in that terrible accident. I thought it would be good to spend some time with him. You're not the only one who needs me, you know." Her cheeks bore the glow of one who has just come in from in from the cold... or warmed up to an...

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