All That I'm Living For

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Shy man, transgender woman get together.
2.3k words
4.37
26.5k
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It wasn't my decision to go to the Midwest. But when one works for a corporation in this day and age, you go where they tell you to go. And when their Executive Manager in Chicago was poached by another corporation, they transferred me to the Windy City.

I wasn't new to the position, having been the Executive Manager in Los Angeles and having won 3 awards there for my work. And probably I was sent because I had no ties. No family, no friends outside of work, and no romantic entanglements. I didn't believe in that stuff - there would be time for it after I retired. Or so I thought.

I let the manager of the apartment complex I was living in know, found a 1-bedroom in a suitable area of Chicago, and arranged for the movers to help pack my stuff and get it shipped. And on my first day of work in Chicago, I felt right at home. I had meetings with my new subordinates and let them know my expectations. I didn't have much to move, so unpacking was easy. Within a few days I was all settled in. And with everything unpacked, I could now buy food and cook it instead of living on restaurant food. (Though the Chicago pizza was as good as advertised: I resolved to order it at least twice a month for dinner.)

I drove out of the work parking lot on Friday evening and went home, then looked to see what sort of grocery stores were nearby. Saturday morning, I went to one that seemed to have good reviews by the locals and was only a few blocks from my apartment.

And everything changed. Because that's where I first encountered Vicki.

She was dressed in the store uniform, stocking shelves with various flavors of Ramen. Slim, not large-chested (as far as I could tell), toned, with legs as long as mine (and I'm 6-foot-1), with straight black hair, just past shoulder length, and a very pretty face.

I didn't see the face at first. I had a question. "It's my first time in here. Where can I find the tortellini?"

She turned from her stocking to address me, and that face, with her charming smile and soul-capturing eyes, imprinted itself instantly into my brain. I was overwhelmed at once.

"Aisle 11, sir."

I dropped my eyes to the floor, and in the loudest voice I could muster - a barely audible croak - stammered, "T-thank you."

Now I had an issue. I knew from previously working "on the floor" in stores that because of the power differential, I couldn't just walk up to Vicki while she was working and ask her out. But other than that she worked at the local grocery store, I knew zero about her.

While I pondered that, I made trips to the store almost every day, just buying a few items at a time. On the occasions I saw Vicki, my face would turn bright red and I would be unable to speak. I could only admire her from a distance, as I couldn't even summon up the fortitude to walk my cart past her.

One day, I was next in line to be checked out. The cashier finished with the customer in front of me, then said politely, "Excuse me for a moment: I'm scheduled to go on break. Someone will cover for me."

10 seconds later, that "someone" appeared. Vicki.

"Will that be cash or charge, sir?"

I attempted to form words, but couldn't. I managed to hold up my card in my hand while staring at the floor.

The woman bagging turned to Vicki and said in a low tone, "He's got a huge crush on you."

I don't think I was supposed to hear that, but I did. My face turned even redder and I managed to nod. I lifted my face back up long enough to run my card.

When I got to my car, I loaded my purchases in the back and then just sat on the hood, burying my face in my hands for a while. What was it about Vicki that turned me into a stammering cretin? Why had I made a total fool of myself by being unable to say one doggone word? All I had to do was say "Charge." I couldn't even manage that.

Cars came and went in the parking lot. I remained seated on the hood of mine, cursing myself for being a fool. I shut my eyes and tried to figure out what was wrong with my brain.

"Are you all right, sir? You've been sitting there for an hour."

The friendly voice broke into my dark thoughts. I unloaded all my frustration on the employee.

"No, I'm not the least bit all right. I'm a damned idiot and my brain won't work around Vicki. Why can't I function around her? It's not the first time I've seem beautiful retail workers, but something about her is different. I've never not been able to speak before." I pounded my fist on the hood in frustration. "I want to ask her out, but the power differential means I can't do it while she's working. But even if I could, how am I supposed to when I can't talk? WHAT IS WRONG WITH ME?"

A long, sharp fingernail jabbed my neck from behind.

"Nothing. You're not the first man who my beauty has made tongue-tied."

How long had Vicki been standing behind me? How much had she heard?

"I heard everything."

I started looking to see if there was a nearby hole in the ground I could crawl into.

"Here's my address, shy boy. I'm off work tomorrow. Be there at 6 p.m. on the dot."

She handed me a slip of paper. I carefully pocketed it.

"T-thanks, Vicki." My face was still red, and I couldn't look at her. "I'm Joe."

"OK, Joe. See you tomorrow. And you can dress casually. Well, I have things to do now that I'm off work."

She flashed a smile and sauntered away. I got back in my car and drove home.

The first thing I did was MapQuest the address Vicki had given me, to plot my route. It was only about a 5-minute drive from my place.

The next evening, I showered, put on clean casual clothes, combed my hair, checked the directions one more time, and proceeded over. I rang the doorbell of Vicki's apartment at 5:58.

"Hi, Joe. Come in." She held it open for me.

"Thanks, Vicki." I still couldn't meet her eyes with mine.

She took me into the living room and we sat on a couch. The smell of pizza emanated from a box on the table, and there were two paper plates. She opened the box up. "Dig in."

The next 10 minutes were silent except for the sounds of two people chewing and swallowing. Only two pieces out of the 8 that had originally been in the box were left.

"This will surprise you, Joe, but I haven't been on a date in 6 months."

"What?"

"People are either too shy to approach me (like you were), or they don't want to date me."

"Why?"

I was making progress. At least I could speak.

"I'm packing." She lightly kissed my neck. "But don't worry. I'll be gentle."

My brain seemed to shut down. What had I gotten myself into here? But it didn't matter, I decided. Vicki was gorgeous and I would be thrilled to be with her.

"Okay."

We both made a stop in the restroom, then Vicki led me straight to her bedroom.

"Normally I'd suggest we get to know each other. But I haven't had sex with a live person in way too long."

"I'm not complaining, Vicki."

We stripped down and climbed into her bed.

"Kissing is the usual starting point."

I took the hint and moved my lips to hers. We kissed, softly at first, then more insistently, parting our lips and twining tongues until we had to break for air.

"Not bad, Joe. You may kiss my chest."

I slipped my body downwards a bit, tentatively kissing her cleavage.

"While I appreciate your gentleness, right now I'm really horny. You can speed up the foreplay."

Vicki guided my mouth to her nipple. I suckled on it, and she moaned appreciatively. She helped me move my mouth to her other nipple, and I suckled on that one as well.

Vicki disengaged me from her chest and lay me on my back. Then she kissed her way expertly down to my chest, tracing intricate patterns with her tongue on my skin that sent shivers through me. I hadn't realized my own nipples were so sensitive.

She noticed my stiff rod and teasingly reached a hand down to it, lightly brushing my balls with her fingertips. I shuddered.

"How long has it been since you've cum last, Joe?"

I had to actually pause for thought. I had never been much for masturbating. "At least four months."

"Then before you fuck me, I need to take the edge off. Otherwise you won't last a minute."

She wrapped her hand fully around my rod and sensually stroked it. The cum began boiling up in my balls right away.

Vicki slowed her pace. I was already practically on the edge. Moving her hand gracefully, she eased a few spurts of cum out of my cock.

"That's better." She used the cum to lube my pole. "Now I ride you."

She repositioned herself so that she could wiggle her bumhole downwards onto my rod. It felt very tight. She was facing me, so I could see her pert, firm breasts and stunning face with the soul-capturing eyes.

"Vicki, that feels wonderful."

"Then you'll love this, Joe."

She slid very slowly up and down. Her back-channel gripped and squeezed my rod like I was inside a velvet glove. The moans I was making let Vicki know exactly how much I was enjoying it.

I noticed that her pole wasn't quite fully hard. "How about you?"

"This is wonderful, having someone to fill me up again."

She continued to ride me, placing her hands on my chest to assist in keeping her balance. I tentatively placed mine on her hips. She gave me a smile. I helped guide her up and down as my balls started to tighten.

"Oooh, Joe. Are you going to cum inside me?"

"Yes, Vicki."

"Do it. I want to feel your cock throb as you blast your load."

Her dirty talk turned me on even more, and she squeezed me more intently. My body tensed up.

"Vicki..."

I injected my sperm into her rear. She pinned me down and squeezed my cock until I stopped spurting.

When my pole started softening, she climbed off me. "That's exactly what I needed, Joe."

"But you didn't cum," I protested.

"Oh, but I did. I just didn't shoot sperm. The hormones make that harder for me, you know."

"But..."

"I suppose I did kind of promise to be inside you. I'm an honorable woman, so I better keep to that."

She dripped a bit of lube on her pole and spread my legs. Then she slowly worked her rod, now fully hard, into my rear.

"This'll take a while. And it's a special thing. I prefer to take it in the ass rather than give it. In fact, eventually I plan to have the surgery."

"In that case... thank you, Vicki, for going out of your comfort zone for me."

"Thank you, Joe, for being such a sweetie and letting me use you for sex right away."

We both fell silent except for the sounds of our increasingly heavy breathing. Vicki was very gentle, just like she said she was going to be, and it felt surprisingly good. In fact, my cock was getting hard again.

"Even two wasn't enough, huh? I guess you had a lot built up after four months."

Vicki reached a hand down and began pumping me in the same rhythm as she was fucking me. Her other hand was caressing my balls.

"Vicki, you're amazing."

"Flatterer."

She continued her steady rhythm. I lay still and let out a series of moans as waves of pleasure flowed through me. Vicki gradually sped up the pace of both her hand and her hips.

I looked into her eyes. They were smiling, and I felt happy. She continued thrusting into me and pumping my pole. I moaned more intensely and my body began tensing up. Her cock began twitching.

"Ready?"

"Yes, Vicki."

She squirted into my back-channel right as my balls gave up yet another load of cum, this one fountaining into the air. She kept moving her hand until she was sure she had all of it out.

"I think this time you're drained."

I pulled her face close and gave her a kiss. "Thank you, Vicki. That was... amazing."

We climbed off the bed and cleaned up together in the shower. I coundn't resist kissing her nipples and groping her butt.

"Time to rest, hon," she murmured. We got out, dried off, and slipped under the covers. Vicki held me from behind and gently kissed my neck.

"Thank you again, Vicki."

"Thank you, Joe. You made me feel great."

We fell asleep and I woke the next morning still securely in Vicki's strong arms. When I climbed reluctantly out of her bed, she gave me a smile.

"I'd love to spend more time with you, Joe."

"I'd love to be in you more often, Vicki." Then I realized what I'd said. "Belay that! WITH you more often."

She held my gaze with hers. "In me works. Y'know, I can barely afford this place on my minimum-wage salary. And you seem like a nice guy. Perhaps we can make a deal."

"What sort of a deal?"

"You let me move in with you. I quit my job and in lieu of rent, you can fuck me as often as you want. I'd prefer it to be every day, but if you're not up for it..."

"I think I can manage every day."

So I moved Vicki in with me. Keeping up with her sexual needs isn't easy, but the rewards are well worth it.

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2 Comments
DianeTGDianeTGover 5 years ago
A cute story

I really liked this but I think after the very realistic and tantalizing beginning, the consummation came too soon, (No pun intended) I would love to have seen more of a courtship and some emotional struggle before Joe and Vicki ended up living together.

AnonymousAnonymousover 5 years ago
5 stars

I love this story, IF only things worked like that. Surprised at the unsafe sex to start the relationship though.

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