Jimmy meets Miss Victoria

Mar 27, 2024 // By:analsex // No Comment

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Anri Okita

This is my first submission to Literotica. It is based on fact, but not entirely true. There was a Victoria in my life, but the Victoria in this story is a composite of three women who introduced me to the pleasures of sex and being sexually and sensually submissive to women. I’ve also compressed roughly three years of events into a single year.


It started innocently enough. I was a shy, skinny kid, 5’9″, 140 lbs, 18 years old and a freshman in college. I wouldn’t turn 19 until the following spring. The combination of my being at least a year younger than my peers and being extremely baby-faced led to my almost total lack of experience with girls. So far, that experience consisted of a few quick feels of bare tit and a couple of hand jobs at the local drive-in.

I had a partial academic scholarship to college, so I was working part-time at a local running store to help my folks out with my tuition. I had noticed a few of the female customers (and a few of the males as well) eying me as I helped them pick out their shoes and running gear. My tight shorts showed off my attributes quite well, but I was always too shy to act on the opportunities that were presented to me.

One of our frequent customers was a tall (6′), mid 30’s, self-assured goddess named Victoria. She had short black hair and not an ounce of fat on her trim, fit body. Her ass was tight, round, and muscular, and her medium sized breasts barely jiggled when she walked around the store. Every time she looked at me I would blush from head to toe and quickly turn away. If she asked me a question, I would stammer a quick answer while I looked at my feet. My co-workers teased me constantly about my having a crush on her, which I would fiercely deny. The truth be told, she was often the object of my nightly masturbation fantasies.

One Sunday afternoon, I was working alone in the store. I had a half hour until I could close up shop and I was deeply involved in a running magazine when the bell rang indicating someone had entered the store. I looked up and there she was – the goddess. She was wearing a pair of running shorts and a tank top. Her braless breasts pushed against the top and I could clearly see her nipples poking against the thin fabric.

I stammered a quick hello and asked her if I could help her find something. “Hi Jimmy. I need some new shoes” she said with a smile, obviously enjoying my visible discomfort. I asked her what type and size she was looking for and she quickly told me the names of several models. While I went in back to get the boxes, she sat down on one of the benches. I came out with her shoes and stammered out “Which ones do you want to try on first Victoria?” She looked at me, smiled and said, “My friends call me Vicki.” I smiled, blushed and quickly said “OK Vicki” as I handed her the first pair to try on. She looked at me with that same amused smile and asked me if I could help her put them on.

I knelt down and slowly reached for her bare feet with trembling hands. She grinned and said “Don’t be shy. I won’t break. Besides I’m sure you do this all the time.” I grabbed her feet and slowly started putting her shoes on her, all the while thinking “I can’t believe I’m touching her. Don’t screw up. Don’t let her know how nervous you are.”

As I finished tying her shoes, I looked up and started to say “Why don’t you stand up and we can check the fi….”. I stopped, unable to continue. I was looking up her slightly spread legs and through the gap in the leg of her running shorts I could see the white lace of her panties. I couldn’t believe it, I was looking at a woman’s panties. Not the boring cotton panties that my mom and sister wore, but real lace panties on a real woman. I couldn’t move. I couldn’t talk. Hell, I could hardly breathe. I forced myself to look away as she stood up. She slowly moved around and I asked her how they felt. “They seem OK, but let me try on the other two pair.”

I continued to kneel at her feet as the routine was repeated for the other two pair of shoes. However, I noticed that with each pair, her legs ever so slightly spread further and further apart. With each pair, I fought the urge to steal a glance, but that was a losing battle. After the last pair of shoes were on and laced up, I noticed that her panties had a small damp spot and I could smell a heady aroma coming from crotch.

“So, which ones will it be?” I asked. “These ones I have on will be just fine” she answered. I quickly grabbed the boxes and stood up. A slight chuckle came from her as I stood and I noticed she was staring at my running shorts. “Is that for me?” she asked with a sparkle in her eyes. I looked down in horror as my erection pushed out at the front of my running shorts, a large wet spot clearly visible. “Oh my, god”, I thought. I had been hard since the first glimpse of her panties and I didn’t even notice it until now. “I….I’m….I’m sorry….” I stammered as I blushed again and tried to back away.

“That’s okay sweetie. I’m flattered.” Then she reached out and gently grasped my erection Antep Bayan Escort through my shorts, all the while looking deeply into my eyes. I couldn’t turn away from her gaze and after two quick strokes I shuddered, as my cock exploded and cum filled my shorts. She leaned forward, gave me a quick kiss and whispered in my ear, “I’ll be in my car in the parking lot. Close up the store and don’t make me wait too long.” With that she was out the door.

My first thought was “she didn’t pay for the shoes.” My second thought was “you dumb fuck, pay for them yourself and get your ass outside.” I was on autopilot as I closed up shop in record time and rushed out the door. She was waiting for me as promised and I jumped in the passenger seat. She looked at my shorts again and smiled. “We’ll have to get you cleaned up.” My face flushed again as I realized that in my haste to close up I hadn’t stopped to clean my cum soaked shorts. “I….I’m….I’m sorry….” I stammered again.

“Don’t apologize. Besides, you’re cute when you blush.” I turned an even deeper shade of red as she continued “I think I’m going to have fun with you, I hope you’re ready.”

The short drive to her house was silent as I wondered what she meant with that last statement. She pulled up her driveway, shut off her car and turned to look at me. “Follow me” was all she said, and with that she was quickly out of the car and on her way into her house. I did as she told me, all the while watching her ass in her running shorts. I couldn’t believe my luck, but at the same time I was nervous, unsure of what was to follow.

Once inside, she turned and told me to go in her guest bathroom, put on a robe she had in there and give her my clothes so she could wash them for me. I came out, still embarrassed about what happened at the store and sat down in her living room, where she was waiting for me. She handed me a glass of wine and said “I know you’re not supposed to have this, but you’re a college man now, so relax and enjoy.”

Leaning back and sipping slowly from her wine glass, she continued. “So Jimmy, I’ve seen you at the store for a couple of months now and I hardly know you. Tell me all about you. Where are you from, what are you taking in school. Tell me everything.” I proceeded to tell her about my family, about being in college, how I enjoyed it, but didn’t seem to fit in because of the age gap. She asked if I had a girlfriend in college and I blushed again and told her no. She then asked me about my high school girlfriends. I stammered a quick reply, “I didn’t really have a girlfriend in high school” and took a big drink of wine, trying to calm my nerves.

“So, you don’t have much experience with girls?”

“Not really.”

“Have you ever slept with a girl?”

I hesitated, dropped my head and stammered the beginning of a reply. “Nu….nu….no.” I could feel the flush spread over my face.

“What about a blow job? Surely you’ve had some sweet young thing give you a blow job?”

I didn’t think it was possible, but my face got even redder. I gulped down the rest of my wine and quietly answered “No.”

“How about a hand job then? Hasn’t a girl jerked you off?”

I almost whispered my reply. “No one has ever touched me that way…..except for you, today.”

“Don’t worry sweetie”, she said, reaching out to grab my hand. “I’m sure you’ll find the right girl soon enough.”

“How?” I asked with a degree of irritation. The wine had kicked in and my normal shyness seemed to melt away. “In case you haven’t noticed, I’m 18 years old, I look like I’m 14 and I can’t growth facial hair to save my ass. I’m surrounded by college girls who all want to be with older guys and I look like their little brother! Even worse, every time I’m near a girl I like, my brain freezes and I turn into a stammering idiot. At this rate I’ll die a virgin.”

Vicki was silent for a moment, and appeared to be in deep thought. Then she smiled, leaned in close to me and took my face in her hand. She stared into my eyes and she had the look of someone who was in control and knew it. “Here is the deal Jimmy. You have two options. Option 1 — You can stay, and I can help you with your little problem, but if you stay you have to do exactly as I tell you. No exceptions. One refusal and playtime is over… you leave immediately. Also, no one is to know about our agreement. No shop-talk at work, no bragging to the boys at school. Option 2 — You can get dressed, I’ll pay you for the shoes and you leave. We’ll be friends, but ONLY friends and what happened this afternoon will just be a nice memory.”

She looked at me, waiting for my reply, but the slight smile on her face told me she already knew my answer. “I’d like to stay, Vicki” I quietly answered. Her smile grew even larger. “Okay, but remember, you MUST do as you’re told and from now on you will call me ‘Miss Victoria’, ‘ma’am’ or ‘Mistress’. Oh, one more thing, I promise you it will be worth it.” I lightly licked my lips and shyly answered “Yes, Miss Victoria.”

Vicki stood up said “Good choice Booby. Now come with me” as she headed upstairs. I quickly followed her, nervous, but at the same time excited about what I thought was about to happen.

We entered her bedroom and Vicki sat at the end of her bed and motioned me forward.

“Strip.” One word. One command. That was all she said. That was all it took. “Yes Miss Victoria” was my reply as I quickly removed the robe. Within seconds I was standing nude before her, erect and trembling. Vicki looked me up and down with an appraising eye and then slowly twirled her finger, indicating that she wanted me to turn around. I did as she wanted and finished up facing her again.

“You have a nice body Jimmy. You have a nice sized cock, not too big, not too small, and it’s nice and thick. Your balls are extremely big for a boy your size.” My face flushed deeper as she continued, “Your ass looks good enough to eat and I really like that you don’t have much body hair. You’ll look even better with it all gone.” I wasn’t really sure what she meant by the last comment, but I was pleased that she wasn’t disappointed with my cock (like most guys, I secretly thought my cock was too small).

“So tell me Jimmy, have you ever seen a naked woman? Not pictures, but a real, live naked woman?”

“No Miss Victoria. I only saw my sister naked once when she was 10, but never a real woman,” I answered.

“Would you like to see me naked Jimmy? Would you like to see my tits and pussy? Would you like to see my ass? I guarantee it will be better than looking at your little sister” she said.

“Oh god, yes Miss Victoria.”

“Then back up and watch Jimmy. But no touching. That means no touching me and no touching yourself.”

Vicki slowly stood up and with a twinkle in her eyes, she started undressing. She turned around and put her feet on her bed to take off her shoes. I never imagined that watching someone take off their shoes could be so hot, but it was. Her shorts rode up her ass and I gasped out loud when I caught another glimpse of her pantied pussy. She then turned and pulled her top over her head, dropping it on the floor. I could hardly breathe as I stared at her perfect breasts. Next came her shorts, slowly working their way down her legs. All that was left were those white lace panties that had started all of this. As she turned around again I could see that she was wearing a thong. Vicki looked back over her shoulder and smiled as she pulled down her panties, bending over to show off her ass and quickly giving me a glimpse of her bare pussy lips. She turned around for the last time and stood still before me, hands on hips, proudly displaying her nude body to me.

She was beyond any of my late night imaginations. Her athletic body was perfect. Her breasts were firm and her nipples were hard. Her pussy was completely shaved, her inner lips swollen and hanging slightly lower than her outer lips. Her clitoris was clearly visible and her wetness glistened on the insides of her thighs. My cock grew harder (if that was even possible), and pre-cum began to drip from the end. My balls ached to release the load that I was close to losing. It took all of my willpower to keep from jacking off right there.

“I take it you like what you see” she asked, smiling and looking at my throbbing cock.

I quietly whispered back, “You’re beautiful Miss Victoria.”

Vicki moved closer to me, not quite touching. She leaned in close and whispered “You look like you’re ready to explode Jimmy. Let me take care of that hard cock for you and then we can get started on the real fun.”

With that, Vicki sank to her knees and quickly engulfed my cock, sliding her hot, wet mouth all the way to the base. My knees nearly buckled as I grabbed her head for support. This caused her to groan out load and she began to move her mouth up and down my cock.

I would love to lie and tell you I lasted forever. Tell you that she had to beg for my cum before I finally gave her what she desired. However, I was like most young boys faced with the reality of their first blow job. I lasted all of 10 seconds before I exploded in her mouth. I tried to warn her, but all that came out was a strangled “I’m cuuuum….” before my hot cum jetted into her mouth.

Vicki took my load like a pro, holding the end of my cock in her mouth as I filled her with spurt after spurt of cum. I knew from my past sessions of self pleasure that it would be a big load. She looked up at me and as my glazed eyes took in the vision of her sucking my cock she made a point of opening her mouth to show me the cum pooled inside. She swallowed my load and rubbed my still leaking cock across her lips before putting it back inside her mouth, cleaning up the last few spurts and dribbles.

Vicki rose to her feet and gently brought her mouth to mine, kissing me deeply and lovingly. I realized that I could taste my cum on her lips and in her mouth, but I didn’t hesitate, I willingly let her kiss me as long as she wanted.

Vicki slowly broke off the kiss, looked into my eyes and asked me “So Jimmy, what did you think of your first blow job?”

“That was incredible Miss Victoria. I don’t know how to thank you.”

Vicki’s eyes sparkled and her smile widened as she said “Oh, I think we can come up with some way for you to thank me. Sit down Jimmy” she said as she sat on the bed, patting the space next to her.

“Do you trust me Jimmy? I want you to think about what I have to say before you answer me.”

“I can show you so many different ways for you to feel good. I can show you ways to make your partner feel good. Some of the things I will show you may seem strange or different at first, but if you trust me, I promise you that in the end they will all feel good.”

“So, Jimmy, the question remains. Do you trust me? Are you willing to do exactly what I say and trust that in the end it will lead to that same good feeling you just had? Do you want to be a good boy and trust Miss Victoria?”

I quickly answered “Yes Miss Victoria. I want to be a good boy. I want to learn how to please you.”

With that, Vicki smiled, took my hand and led me into her bathroom.

“First off, we have to get that hair off of you. I like my boys smooth and hairless” she said as she got some things out of the cabinet and put them on the counter. There sat a bottle of hair remover, shaving cream and a razor. Being a late bloomer, I only had a small patch of pubic hair, and no chest hair to speak of. Even my legs were sparsely populated. All that didn’t matter as Vicki led me to the shower and quickly covered me in hair removal cream.

While she waited for the cream to work its magic, Vicki explained to me that while my being hairless was mainly for her personal pleasure, having a smooth body would make me even more sensitive. She told me that she shaved all of her lovers and once they got used to it all of them ended up keeping the look.

With that she turned on the shower and proceeded to rinse me clean. She then grabbed the shaving cream and lathered up my cock and balls. My erection had returned and as she grabbed my cock, she told me to stay still because she didn’t want to nick “my boys.” I stood perfectly still as she went to work and before I knew it I was as bald as a baby.

Vicki looked up at me. “Almost done sweetie. Turn around.”

“Turn around? Why?”

Her voice suddenly grew hard as she said “Jimmy, do as you’re told.”

I turned around and was promptly smacked hard on my ass. I yelped loudly and Vicki said “That was for not doing what you were told the first time.” She smacked my other cheek and said “That was for not addressing me in the proper manner.” Another hard smack was followed with “And that was for getting me upset. That was your first and last chance Jimmy, do you understand?”

I hung my head and quietly said “Yes Miss Victoria. I’m sorry.”

Vicki stood up, put her finger under my chin and lifted my face up to look into her eyes. With a stern voice, she continued, “I don’t like to punish you Jimmy. Spanking should be done for pleasure, not for punishment. That’s why I told you that I require complete obedience. Are we clear on this, because one more slip up and playtime is over.”

“I’m sorry Miss Victoria. I’ll be better. Please don’t make me go.” I couldn’t stop the tears that began to form at the corner of my eyes. I had been with this beautiful woman for barely more than an hour and already I couldn’t imagine being without her. It wasn’t just the thought that I could be turned away without finally losing my virginity. I realized then that I wanted….. no, I needed to be controlled by this woman. Vicki had flipped a switch deep inside my psyche and I knew that submitting to this goddess was what I truly desired. I knew then that I would do anything to please her.

She reached up and wiped the tears from my cheeks, as a motherly look came over her face. She reached for me and drew my face into her chest, my tears continuing to flow. “Don’t cry baby. Momma only wants the best for you.”

Momma? Momma? My tears slowly stopped as I realized that hearing her calling me baby and herself momma was strangely exciting. I wanted to be both commanded and mothered by Vicki.

She covered my face with little kisses and when my crying finally stopped, she drew back and asked me if I was ready to continue.

“Yes ma’am. I’ll be good”

“Good answer Jimmy. Now turn around and bend over sweetie, because I’ve got to get that tasty little ass of yours as smooth as the day you were born.”

I smiled and did as she told me. Vicki spread shaving cream in my ass crack and quickly removed what little hair I had growing there. She gave my ass a playful smack and proclaimed “All done baby. Now rinse off real quick so I can see how nice you look.”

The shower made short work of the clean up and as Vicki dried me off I marveled at how nice her touch felt. I wasn’t just the new found joy of being touched by a woman (a naked woman at that), but it was amazing how nice her hands felt on my smooth skin. Vicki quickly rubbed lotion all over my body to “help keep you smooth.” With that she took my hand and led me back into her bedroom.

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