Kelly's First Date Ch. 02

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Kelly gets taught by older men.
4k words
4.18
19.5k
14

Part 2 of the 4 part series

Updated 02/23/2024
Created 06/03/2023
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hoover789
hoover789
306 Followers

Kelly Two

I had a rotten night's sleep. I was sore all over; my privates were red and painful. I had bruises on my arms and legs where he had grabbed me. My boobs hurt so much that I couldn't imagine wearing a bra.

As I lay there, I wondered what would happen next. I was supposed to go home soon. I couldn't imagine living there again.

I glanced at my watch. It was a little past eight o'clock. I could smell coffee, but I hadn't heard Vicky. She usually made some noise. She was definitely a morning person, but not today.

I slipped my robe on. I had slept naked for the first time in my life.

I walked into the kitchen and poured a cup for myself. Walking down the hall, I noticed Vicky's door was closed. I knocked lightly. There was a pause, and then she said to come in.

It was the first time I had seen her without makeup. She looked tired and sad. Vicky sat up and patted the bed beside her for me to sit. She spoke softly.

"I feel so bad about last night. I should have never put you in that situation."

"It's not your fault, Vicky. I should have known what to do. I'm a big girl now. I have to learn about guys and what they want, and won't get that at home; I want to stay with you."

"We'll see. It will be hard to convince your mother; I don't have to tell you how she is. Now come here and hug me; I really need one."

As I leaned forward, my robe fell open, exposing my firm boobs. Vicky gasped,

"I didn't realize he roughed you up so much. Your poor tits are all bruised."

Vicky pulled me closer and gently nuzzled my firm boobs; I welcomed her hot mouth despite the pain. Her tongue snaked out to my sensitive nipples, her lips enveloping my hard nubs. I moaned softly, wrapping my arms around her head and mashing my tits on her face. My pussy was on fire. I needed to cum. Letting my robe fall off, I straddled one of her legs and rubbed myself. Vicky was naked under the covers. We embraced, our lips finding each other, her tongue invading my mouth, kissing me deeply.

I started to trail kisses down her body, working on her nipples and then her belly. She took my head and guided my face to her shaved mound.

"Use your mouth," she hissed. My tongue snaked out and found her clit. She was moving her hips, forcing me deeper. I kept licking and biting gently, not knowing if I was doing it right. I could only go by Vicky grunting with pleasure. Her long legs gripped my head. She finally tensed up and held me tightly while her body shook with an intense orgasm.

We lay quietly, arms and legs entwined. With a sly smile, she kissed me tenderly and said, "Your turn."

Half-heartedly I said no, but she knew what I wanted.

Vicky took something from her nightstand and put it under her pillow.

"What's going on?"

"Don't worry, just relax."

We kissed, my tongue finding hers as her hand strayed to my tender pussy. I opened my legs, inviting her fingers to explore.

I was wetter than the first time she had touched me, my body aching for release.

"Close your eyes," she said, reaching under her pillow. Afraid to open my eyes, I felt her move down. I was trembling, waiting for her hot mouth to find me. Instead, I felt something hard probing my soft pussy. My eyes popped open. Vicky had a flesh-colored cylinder that was pointed at one end. She slipped it into my dripping slit a few inches.

Smiling, she said. "Bend your legs a little I'm going to go in a little more."

It wasn't as big as Fred's dick, but it felt good. She was rubbing it on my clit and then in and out, each time going a little deeper. I was in ecstasy. Pulling it out and concentrating on my clit she switched it on. The gentle vibrations drove me crazy; I reached down and put my hand over hers. Guiding it to the right spot. I moved it by myself, hitting the most sensitive spot. The size and vibrations were unlike anything I've experienced. Finally, I tensed up and exploded. I lay there trembling with my mouth partially open. I love this thing.

"Vicky, may I keep this in my room?"

She smiled and kissed me softly on my neck.

"Sure, it's yours to keep." Then chuckling, she said, "What have I created?"

"Let's stay in bed all day," I said, wrapping my arms around her.

"My thoughts exactly," Vicky said, nuzzling my neck.

We slept most of the day in each other's arms. Vicky was the first to get up. Wrapping her robe around her, she said. "Come on, sleepy head, let's go out to dinner."

Wiping the sleep from my eyes, I headed to my shower.

I felt sexy and wanted to show off. I wiggled into the corset Vicky had bought me. It fits me perfectly. My tits were supported but not hidden, with the tops exposed. I slipped on sheer brown stockings and put my hair in an upsweep.

Just as I was zipping up my dress, Vicky walked in.

"Look at you, you're gorgeous."

I turned bright red.

"Stop it. It's all thanks to you."

We decided to eat downstairs to drink and not worry about driving. After eating, we lingered over our drinks. Vicky seemed to have something on her mind. Finally, she leaned toward me.

"I have to go away this weekend with a client. And I've got a job for you."

My stomach did flip-flops as I reached for my wine.

"You know how we never pay for our meals? Well, they're not free. I spend the night with Perry, the manager, once a month when I'm here. Before you get nervous, he's very kind and doesn't expect much."

"And you want me to take your place?" I whispered.

"You'll be fine. We'll talk later; let me get you another glass of wine; you look pale," she laughed.

Later in her apartment, we sat on the couch. Vicky took my hand.

"You had a bad first time. Most men are easy and quick."

"What do you mean quick?"

"Play around with them a little, show them your body, then a little cocksucking, and they'll last about two minutes when they get their dick in you. And with your tits, maybe only one minute. Now stop worrying and go buy a new dress tomorrow."

Friday rolled around, and Vicky left around nine o'clock, leaving me very lonely. I wore a pale-yellow garter belt with a matching bra and panties. I chose a light white sleeveless dress, suntan stockings, and white heels. Thankfully the doorman knew the address of the shop and hailed a cab. I felt very grown-up.

I picked out two black dresses. One had a plunging neckline that looked super sexy, the other was tight and short; of course, the staff fawned all over me. I felt so empowered.

I had just finished lunch when Perry called, told me his room number, and asked if eight o'clock would be all right. He sounded so polite. I said, "Sure." Hoping I didn't sound too scared.

I chose my waist cincher, a demi bra, and sheer black stockings. The dress was snug and highlighted my hourglass figure. The scoop neckline left little to the imagination, showing the tops of my boobs nestled in the lace cups. A black choker completed my outfit.

The door to his suite was partially open. I knocked lightly.

"Come in, Kelly. Good to see you." He was tall, very tan, and a gentleman, but looked much older than I remember. I noticed how much heavier he looked in casual clothes.

He brought a glass of wine and a drink for himself. We sat on a couch overlooking the city.

We talked about the weather and his restaurant, which he was very proud of.

We sat quietly for a minute. He turned toward me and lightly ran his fingers over my cheek.

"You're a very beautiful young woman."

Turning my head, I leaned to him, and our lips met, our tongues probing each other.

His fingers moved to my tits, giving them a light squeeze. I lay back, holding him close as we kissed deeply. He wasn't as gentle as Vicky, but my pussy still tingled, begging for a touch.

We relaxed momentarily, finishing our drinks, his hand resting on my knee. I spread my legs slightly, offering access to my thighs. He kissed me again, starting to slide his hand up my legs. Reaching my stocking top, he paused briefly before brushing my mound. Then sliding under my panties, seeking my tender pussy. Gently his finger slid into my wetness.

"Aaaahhhhh, don't stop," I groaned as his fingers explored me. He found the right spot, manipulating my clit. He kept gently massaging my tender folds until I had an intense orgasm.

I was still panting when he took my hand and led me to the bedroom. I was trembling as he unzipped my dress and let it fall to the floor. He sat on the bed and told me to turn around. He stopped me when my ass faced him, taking time to explore my taut butt. I felt so self-conscious, like I was being inspected.

He quickly stripped; his dick looked huge; after more experience, I would realize it was just average.

Standing before him in my nylons, bra, and panties, my waist cincher nipping my waist in. He surveyed my body.

"Your perfect," he smiled. "Take off your bra; they shouldn't be covered." My hands shook as I reached for the clasp unhooking it, and my firm tits leaped out. He pushed them together, putting his face between them, slobbering on my tender boobs.

He alternated between biting and sucking my tortured nipples.

His hands were all over my body. Pulling me onto the bed, he guided my head to his cock.

"Put it in your mouth."

Gingerly I licked the tip of his cock. Almost immediately, clear liquid started dripping out. It tasted salty; I guessed I was pleasing him.

He held my head, guiding me up and down, telling me what a good cocksucker I was. I guess I should be flattered. I really wasn't sure what I was doing.

He kept jabbing at my throat, causing me to gag.

I was beginning not to like it.

"Abruptly, he pulled me up and laid me on my back, getting on top of me, his dick probing at my wet slit.

I spread my nylon-covered legs, urging him in. He took his time, entering me carefully, savoring the moment.

I was nervous. It felt too big but at the same time, just right; I wrapped my legs around him, my heels scratching his back. I loved the assault on my clit.

He slowly moved in and out of me while sucking and biting my nipples.

He picked up his thrusts, going faster with a painful expression on his face. He tensed up, and I could feel his cum squirting in me. He kept thrusting and finally lay on top of me, breathing hard, covered in sweat.

"You're quite a girl. I hope you'll be staying on."

Perry said, getting up. He sat in a chair, lighting a cigarette. I looked at his flaccid dick and proudly thought I had done that. I pulled my panties on and reached for my bra when he held his hand up and said,

"Not yet; I enjoy looking at you."

I didn't know what to do. I felt very self-conscious. I was standing before him in just my nylons, heels, garter belt, and panties. He sat back, sipping his drink. Finally, he said,

"Kelly, play with those big tits."

Vicky had told me that guys sometimes get mean after they cum. So to please him, I cupped my tits, unsure what to do. He wasn't smiling anymore.

"I SAID PLAY WITH THEM, you dumb bitch! pinch your nipples and kiss them."

I was petrified; I got the feeling he would hit me If I didn't do as he said. I started squeezing my boobs and pulling at my nipples, moaning for him. I lifted one to my mouth, sucking noisily, and began feeling sensations in my pussy.

He started playing with his dick; when he stood up abruptly and walked over to me, his dick hardening.

"On your knees, you're not done yet. Now suck my cock.

I dropped to my knees; my stockings pulled tight by my garters. I ran my lips over his dripping cock, looking up at him, trying to please. He gripped my head, forcing his dick deeper, making me gag. He was relentless, jamming his cock in my throat. I was getting to the point of fainting.

The room was spinning, black spots before my eyes. I was jolted back to reality when I felt his cum shooting down my throat. He pulled out, and I fell onto the floor on my side, coughing and gagging.

I lay there for a couple of minutes, not realizing how much cum I had on me until it began to gel. I sat up, wondering if this was what sex was all about.

I could hear Perry in the next room on the phone, but not what he was saying. I took my heels off and put my bra back on. I found my dress under the bed and slipped it on. He was still talking as I put my shoes on and approached him. "Thanks for a lovely night," I said, forcing a smile. He stood up, kissed me on the cheek, and slapped my ass. He sat down and continued speaking on the phone. I opened the door; I could only guess he thought I was gone when I heard him say.

"Oh, she's just some whore from the building. All I can say is she's one talented cocksucker."

My ears burning, I slammed the door.

Later Vicky called to tell me she would be home tomorrow and wanted to know how the date went.

"I mumbled ok." And said I was getting in the shower. Afterward, I made myself a drink, something I'd never done before. After a second drink, sleep came quickly.

Vicky got back around lunch. Neither of us liked the idea of going out, so we ordered from room service. We ate in silence, both too tired for small talk.

Sooner or later, I would have to tell Vicky I didn't like sex with men; they hurt me. The only time I enjoyed it was with her. I put off telling her until tomorrow. We both slept through the afternoon, waking at six o'clock.

We both agreed to go downstairs for dinner. In all the time I was here, we never cooked. I could get used to this life.

I chose a tight tan skirt, a black sleeveless light sweater, and suntan stockings with black heels. While I waited for Vicky, I teased up my blonde hair. I really liked my new look. I could never go back to my old clothes.

Vicky looked glamorous in a form-fitting dark blue dress that ended above her knees, displaying sheer blue stockings.

We ate a light dinner with a couple of glasses of wine. Thank God Perry wasn't there. I did not want to see him now. We went into the bar for a nightcap.

There were mostly couples and a few single men in the darkened bar. Vicky pulled out a stool, and we sat at the bar. If I were alone, I never would have sat there.

The stools were tall, and we showed quite a bit of leg. It was a combination of being with Vicky and the wine. I hitched my skirt a little, letting my stocking tops show to the point of my garter clasps. Vicky looked over and said,

"Good girl, you're learning. Here comes your first fish."

A middle-aged, overweight man came up behind us, putting his hands on the back of our stools.

"Are you ladies alone?"

Vicky ran her hand over her thigh, inching her dress higher, exposing the first of the two darker bands of her stockings.

Vicky turned and flashed her perfect smile.

"For now, what did you have in mind?"

"A drink in my room, for starters. Shall we go?"

"What makes you think we would want to go?" she replied with an icy tone.

"To be truthful, two women alone in a bar showing your legs, I figured you were hookers. I'm sorry if I offended you." He turned quickly and left.

My face was beet red. I couldn't look Vicky in the eye.

"Is that what I look like, Vicky?"

"Don't be silly; he's just a horny old man seeing if he could get lucky. Now let's go back to our apartment.

As we were leaving the bar, Perry walked in. He looked so different in a suit. He hardly looked at me other than to say it was good to see me again. He offered us a drink; Vicky said sure, but I excused myself, saying I had a headache.

When I returned to the apartment, I went straight to Vicky's room and the full-length mirror. I pulled off my sweater and skirt. Looking at myself, my mother would have a fit. My garter belt cinched my waist tight, tugging my dark stockings high on my legs. My bra did little to contain my firm nineteen-year-old boobs.

I was in four-inch heels. I never thought I could walk in them. But now I like them. Maybe I did look like a hooker, but I liked it. I wished Vicky was here to caress my body. She knew just what to do to make me feel good.

I headed toward the bathroom for a shower when there was a knock on the door. Vicky must have left her key. I didn't put my robe on, it was only Vicky, and maybe seeing me in my underwear, she would take care of me.

I foolishly unlocked the door without checking the peep site. Instantly, the door was pushed open, knocking me on my ass. I sprawled on my back, my legs bent. It was the jerk from the pool, Rick, and another guy. I tried to get up, but they kept pushing me down, laughing at my feeble attempts to stand. I was mortified lying there in my stockings and heels. Rick reached down and roughly pulled me up, pinning my arms behind my back.

"You should have let me play with your tities the other day," He snarled. The other guy jerked my bra down, my boobs springing free, bouncing like crazy. "You better get out. My roommate will be back soon."

"Don't worry about that; we're leaving now, and you're coming with us!"

I cried, "You're crazy. I don't have any clothes on." They pushed me to the door. Rick opened it and checked the hall. They half-carried me to a room on the same floor. He opened the door, pushing me in; I went sprawling on the floor. The room was furnished, but no one lived there.

Rick locked the door. As I struggled to my feet, standing before them, I crossed my arms, trying vainly to cover my tender boobs.

"Put your hands behind your back."

I complied, making my tits leap forward, tears flowing down my cheeks.

"Please let me go. I won't tell."

Rick smiled. "Who cares if some whore gets fucked. Now get down on your knees. I dropped quickly, scared of what they might do. He pushed me further down so my butt rested on my nylon-covered legs.

They started jamming their dicks in my mouth. I tried sucking, but they were moving too fast. Much to their delight, I gagged uncontrollably, tears mixing with spit and pre cum dripping on my jiggling tits.

"Let's have some fun with her."

I cried, "PLEASE...Please let me go!" They ignored me.

Rick pulled my arm up and dragged me over to the bed. Roughly spreading my legs and, without hesitation, he ripped my panties off and covered my pussy with his mouth, licking and biting. I gasped; it felt good, and I might have enjoyed it more if his friend wasn't forcing his cock into my mouth.

My hands gripped his head while I spread my legs, giving him more access. Rick looked up, grinning, his face covered in cunt juice.

"I told you, girls that dress as she does; love to fuck."

He went back to licking my clit. I couldn't hold back anymore; I squeezed his head between my stocking-covered legs and had a wild orgasm.

"Lady, it's time for you to fuck."

He pulled me to the edge of the bed, dropping his pants and exposing his throbbing cock. He guided it into me in one motion, knocking the wind out of me. But I recovered and thrust back, meeting his.

"You won't believe how tight this snatch is. You have to get some of this."

They talked about me like I wasn't there.

Rick speeded up and then froze, pumping his cum deep in me. He rolled off of me as his partner erupted down my throat. He pulled his cum spewing cock out of my mouth with a wet pop and wiped it off in my hair.

Rick had a bottle of whisky they were drinking from, he offered it to me, but I shook my head no.

"Come on, loosen up; we're not done yet."

He held it to my lips and said.

"If you spill any, I'll be very unhappy, and you don't want me unhappy."

With that, he poured some into my mouth. I sat up and swallowed it. He kept my mouth full until I told him I was getting sick.

It had just the effect he wanted; I didn't complain when his friend told me to get on all fours, doggy style. He got behind me, probing my swollen cunt with his dick while snapping my garter straps.

He entered me with ease and started pounding me.

hoover789
hoover789
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