Tales From My GF's Past Ch. 01-02

My name is Keith and right after college, I went to work at a large health care insurance company. I did back-office support and was paid decent money so I moved 100 miles away and began to establish some new friendships. I'm not the most outgoing guy and making new friends was difficult for me. Our company had several floors in a downtown office building and I'd see people in the elevators or cafeteria but only knew them well enough to give them a "good morning," or "have a nice night."

One Monday morning, I was half asleep when I got onto the elevator and I heard a female voice say, "Hold the elevator, please."

I instinctively put my hand between the doors to trigger the electric eye so the doors would open and a gorgeous long-haired brunette said, "Thank you. You saved my life. I'm almost late for a meeting."

All I could muster up to respond was, "You're welcome."

She smiled at me but I was too shy to say anything more to her. What first struck me about her other than her beauty was the fact that she must have been six foot tall or darn close to it and slender. I'm a leg man so my eyes naturally scanned her long slim legs. I would give anything to see more of those legs of hers. I guessed that she must have played volleyball or basketball in school. She was wearing a business suit with a white blouse and I could see her white bra through it. I could smell the bright zesty fragrance of her perfume as I stood off to the side of her.

She must have noticed me glancing over at her because she turned to look at me a couple of times, giving me a little smile. I gave her an uncomfortable grin in return. I excused myself as I got off the elevator before her. I kicked myself for not striking up a conversation with such a beautiful woman but figured she was probably in a relationship with someone.

Throughout the day, I kept thinking about the beautiful brunette I ran into in the elevator. I wish I had the courage to talk to her more but it's not like there was a lot of time to do so either. I wondered if she worked for our company or was only there for a meeting. Each morning, I hoped to run into her again and I practiced imaginary conversations I'd have to get her contact information so I could ask her out. I kept an eye out for her in the cafeteria too but it seemed like she was only going to be a missed opportunity.

It was a stressful first couple of weeks at work. I had just moved to a new town and was just getting settled into my new apartment. I was struggling to learn all of the aspects of my new job and feeling overwhelmed. When two of my colleagues, Cole and Scott, asked me to join them for Happy Hour on Friday I jumped at the opportunity. I needed to make some new friends and a couple of beers to end a stressful week was just what I needed.

Cole and Scott had been with the company for a couple of years and were telling me some of the gossip about which people were the influencers and which people to stay away from because they were trouble. They both were dating women but it wasn't anything serious.

We were on our second round of beers when I noticed the tall brunette from the elevator walk in. My eyes were immediately drawn to her and I asked the guys if they knew who she was.

"Oh, that's Heidi. She works up in accounting," Scott replied.

"I saw her on the elevator last week. She's fucking gorgeous."

"She sure is, but she's dangerous," Cole added.

"How's that?"

"Well, let's say she's the friendly type. She's dated a few guys from work but she doesn't seem to want a relationship with anyone," Scott said.

"Really? Have you guys dated her?"

Cole smiled and replied, "Yeah, she dated both of us at different times and broke both our hearts but she's great in bed."

"It's not cool to kiss and tell but she sure likes to have sex," Scott added.

They wouldn't give me any details but hearing what little they said about Heidi only made her more attractive to me. She was wearing a pencil skirt that came to just above her knees and hugged her slender frame and a light blue cami top underneath a cardigan sweater. She looked classy and sexy at the same time. I couldn't help but keep glancing over at her. She glanced back at me a couple of times and gave me a slight smile. I wasn't confident enough to go over and talk to her though.

I don't know why I feel awkward talking to women. I'm a decent looking guy who played basketball and baseball in high school. I wasn't good enough to play sports in college but I still go to the gym to stay in shape. I'm not quite six foot tall and have dark hair too. Women have told me I'm handsome but that somehow hasn't translated into a lot of confidence when it comes to the opposite sex. I have had my fair share of women and was in a serious relationship for more than a year in college but it's just the way I am.

As we were finishing our second beer, I saw Heidi set her empty glass on a table and started to walk our way. I kept staring at her as she got closer to our table and was captivated by her beauty. It was like I was hypnotized and couldn't take my eyes off of her. I got a little nervous as she got closer to our table. It was apparent she was coming to talk to us.

"Hello boys," Heidi said.

"Hello, Heidi," Scott and Cole replied almost in unison.

"Who's your new friend?"

"Oh, this is Keith. He just started a couple of weeks ago."

We exchanged greetings as Cole formally introduced us. Her baby blue eyes caught my attention as well as her cute dimples when she smiled. I offered to buy another round of drinks but Scott and Cole declined because they were going to meet up with a couple of ladies later on. Heidi told me she'd like another drink so she joined me at the table.

Over the next hour, I had a great conversation with Heidi. I was definitely feeling sparks developing between us. I could only hope she felt the same. She was beautiful, charming, and had a great sense of humor. During our conversations, she revealed that she played volleyball in college which seemed only natural given her height, and that she was tired of the online dating scene. She had been casually dating a couple of guys but she was clear that they weren't exclusive. That gave me the courage to ask her if she'd like to go on a date sometime.

"I've really enjoyed talking to you this evening and I, uh, was wondering if you'd like to go out with me sometime?

"I was wondering if you were ever going to get around to asking me out. I'd love to go out with you sometime."

I was so excited, I wanted to do backflips but I maintained my composure and told her, "You just made my week."

Heidi was busy over the weekend and I still had a lot of unpacking to do so we made plans for the following Saturday. We stayed for dinner at the bar that night, though. We were having such a great time talking that we lost track of time and we were both hungry. The food wasn't anything special but it gave Heidi and me a chance to extend the wonderful evening we were having.

When we were done for the evening, I walked Heidi to her car and faced that awkward moment when you want to kiss someone but you don't want to push things too fast and scare them off. We didn't kiss that night but I knew it was only a matter of time before it would happen. I felt like I was walking on a cloud as I walked to my car. It was a great ending to my second week at my job in a new town.

During the week, I had the opportunity to have lunch with Heidi a couple of times in the work cafeteria. It happened by chance that we were both there at the same time but it was nice to be able to talk to her. We exchanged text messages during the week but it's not the same as talking face-to-face.

On the Saturday of our date, I knocked on the door of Heidi's apartment promptly at 6:00 PM with a small bouquet of flowers in my hand. When she opened the door, she looked stunning. She was wearing a mini jean skirt that showed off a good portion of her luscious long legs. Her top was a deep V-neck white cropped button-down vest. She was an inch or two taller than me and I was glad that she was wearing flat sandals. Her dark wavy hair was pulled back into a braided ponytail. I stood there in awe.

I almost died when she asked, "What are you doing here?"

I was crushed. Did I make a mistake on the time or day of our date? Were we even supposed to go on a date? Was I dreaming when she agreed to go out with me?

"Um, uh, I'm here for our date," I nervously replied.

"Wow, a real gentleman. Most guys send me a text to meet them outside in their car. You brought flowers too."

"I was brought up to treat a lady better than that. By the way, you look gorgeous tonight."

"Thank you, Keith. You look pretty good yourself."

I prefer a woman who doesn't wear a lot of makeup and has that girl-next-door look and Heidi was perfect in that regard. Her perfume made her smell as good as she looked. I felt like I had met the perfect woman for me. That only upped the pressure on me because I didn't want to blow this opportunity.

I naturally held the car door for Heidi. Not only was I a gentleman but I would never pass up an opportunity to get a peek up a woman's skirt. I wasn't disappointed either. As Heidi got into the car, her legs naturally parted and her skirt rode up higher on her legs. I got a prolonged view of her pink lace undies which I assumed were a thong.

I thought I was being discreet when I glanced between her legs but when I looked up, Heidi was staring at me with a slight smirk on her face. I got caught but she didn't seem to mind. It didn't occur to me that she might have let me look up her skirt on purpose.

On the ride to dinner, I had to remind myself to keep my eyes on the road because I was distracted by seeing so much of Heidi's bare legs. When we got to the restaurant, Heidi got out of the car before I had a chance to rush around to open the door for her. Maybe it was for the better so I didn't get caught looking up her skirt again.

Dinner was everything I had hoped it would be. We talked like old friends who hadn't seen each other in years. We had planned on seeing a movie after dinner but we got so carried away in our conversation that it was too late to catch the movie.

We looked at each other like, "Now what do we do?"

The one apparent thing was that we wanted the date to continue. I suggested that we could go to a bar for an after-dinner drink and I could see her contemplating a response.

Heidi broke the log jam by saying, "If this wasn't our first date, I might suggest going back to my place for a drink."

The date was going better than I expected and I quickly responded by saying, "Well, technically this isn't our first date if you count the dinner we had last week and the two lunch dates earlier this week."

She smiled but her response made me realize she wanted to make me work to go back to her apartment when she replied, "So, you consider those dates, do you?"

"They may not have been the most impressive dates but we could consider them dates if we want to."

The ball was back in her court and she was the final judge and jury.

Heidi looked at me and replied, "So, technically, this is our fourth date."

"Exactly," and I stared at her for a response but deep inside I was trying to send a message through mental telepathy by thinking, "Please, please, pretty please," but trying to act cool on the outside.

After a few moments of deep thought, Heidi gave me a dimpled smile and said, "I guess it would be okay if this is our fourth date."

I wanted to jump into the air and pump my fist but instead, I calmly said, "Do you want to get out of here then?"

"Yes, let's go."

I paid the bill and escorted Heidi out to the car. I made sure to hold the car door again and I got an even better view up her skirt. I was 95% sure she did it on purpose. If she was trying to torture me with her sexuality, it worked like a charm. I figured there was a good chance I'd get laid that night as long as I didn't do anything to blow it. The anticipation was killing me.

There was a nervous sexual tension in the air when we got into Heidi's apartment. It was a small one-bedroom place, about the same size as mine. She got us a couple of drinks and we sat on the sofa. I marveled at her long thin legs as she sat next to me. I kept staring at her beautiful face as we talked.

"Is there something wrong? You keep staring at me."

"There's nothing wrong at all. I keep looking at you and can't believe such a gorgeous woman wanted to go out with me. You're smart; you're charming; you make me laugh; and you're so darn sexy."

She looked at me with a sparkle in her blue eyes and our heads started moving toward one another until our eyes closed and lips touched. My goodness, I never felt anything like it before. Heidi's soft kiss was so good, that it almost made me faint. I also got the beginnings of an erection.

When our lips parted, I opened my eyes and commented, "Wow."

We started kissing again but more passionately. I put my hand on her bare leg that I had been longing to touch. Finding no resistance from Heidi, I began to slowly move my hand up and down her soft thigh, going further up her leg with each stroke. My dick was now hard as a rock.

I reached under her skirt to fondle her firm little ass and she grabbed mine as well. I then cupped her breast through her top and bra.

We were in the throes of an adult makeout session when Heidi asked, "Do you want to take this into the bedroom?"

"Hell yeah."

She took me by the hand to lead me to her bedroom. We kissed some more as we began undressing one other. As I removed each article of her clothing, I felt like I was unwrapping a birthday present. Heidi's pert little B-cup breasts perfectly matched her slender body. Her long torso was highlighted by her firm abs and her legs went on forever. Her neatly trimmed bush matched her dark hair.

My six-inch cock was fully erect and my somewhat athletic body was on full display for Heidi. I have some muscle definition in my arms, chest, and legs but could probably lose a couple of pounds around my waist. Heidi seemed to like what she saw as we embraced again and began to kiss.

Our hands explored each other's bodies as I began to finger her pussy while sucking on her captivating breasts. One of her hands was stroking my erection while the other was grabbing my butt. Heidi stopped kissing me only to lead me over to the bed. She gave me a gentle push and I fell back onto the bed as she dropped to her knees.

Heidi had a devilish grin on her face as she lapped at my balls before moving up to lick and mouth the shaft of my cock. I was in 7th Heaven when she wrapped those pretty wet lips around my dick and started to blow me. She seemed to be enjoying giving me a blow job as much as I was receiving one from her. Heidi had me squirming as she expertly used her lips and tongue on my hard dick. I played with her tits and tweaked her nipples as she blew me. I couldn't help but wonder how many dicks she had sucked to get to be that good of a cocksucker.

Heidi gave my balls and cock a luscious tongue and mouth bath for five minutes or so before she stood up, straddled me while proclaiming, "Now, I'm going to fuck you."

I found Heidi's confidence and take-charge attitude to be an enormous turn-on. She held my saliva-coated erection as she slowly slid down onto it, her tight pussy gripping my cock as she began to ride me. I clutched her compact ass as she was fucking me, with her little titties bouncing in my face. Heidi would only slow down long enough to allow me to suck on her nipples before going back to riding me hard. She was one horny bitch that night.

"Oh, your dick feels so good," Heidi said as she fucked me.

"You're such a sexy woman, don't stop."

When she began to tire, I stood up and laid her on her back on the bed without disengaging.

"It's now my turn to fuck you."

"Oh yeah, fuck me, baby. Fuck me good."

I fantasized about fucking Heidi since the first time I saw her and I was now living the dream. She wrapped her legs around my back and used them as leverage to lift her hips to meet my thrusts. We fucked in unison as I looked deep into her lust-filled blue eyes. She began to fiercely rub her clit with her fingers while I pounded her pussy.

Heidi arched her back and announced, 'Oh fuck, I'm going to cum."

She screamed out in pleasure as she began to climax. Her orgasm triggered mine as I shoved my cock deep into her pussy, releasing almost a week's worth of built-up cum from my balls. When we finished our orgasms, I didn't withdraw from Heidi but continued kissing her. I even amazed myself when my dick started to grow inside of her until it was fully erect again.

"You're a horny little devil, aren't you?" Heid commented.

"You're so beautiful and sexy, you make me horny," I replied as I started moving my hips again.

Heidi asked me to fuck her from behind and I was more than happy to oblige. I grabbed hold of that firm ass of hers and began to fuck her hard. I moved my hands all over her svelte body, enjoying the pleasure of touching her breasts, waist, ass, and thighs. When Heidi began to moan loudly and thrust back at me, I grabbed hold of her hair and spanked her a couple of times.

"Keep spanking me," she cried out as she reached between her legs to rub her clit.

We were both grunting like wild animals in the jungle. This wasn't a lovemaking session, we were downright fucking. I kept fucking her hard while she came to her second orgasm of the night. I was getting tired so she climbed on top of me again and rode my dick until I shot another load into her. By this time, we both needed a rest.

Heidi asked me, "Are you going to stick around?"

"Hell, I'll stay as long as you want."

She went to the bathroom to freshen up and then went and got us a couple of drinks. We sat around naked in her bed talking. I could hardly believe I just fucked this gorgeous lady, not once but twice.

I admitted to Heidi that she caught my attention from the moment she stepped onto the elevator on that fateful morning. She told me she recalls thinking I was cute but was too focused on her meeting to say anything to me until that night in the bar but she hoped I'd ask her out. That's why she approached our table.

I think we felt a mutual attraction and the sexual energy was building the more we conversed. The more I gazed at Heidi's beautiful face and her gorgeous naked body, the more excited I got. It was only a matter of time before my dick started to stir again, a fact that didn't go unnoticed by Heidi.

She looked directly between my legs and commented, "Um, if you're up for more, so am I."

Heidi reached over and stroked my dick to a full erection and grinned but I had other things in mind.

I asked her, "Do you have a pair of stockings you could put on?"

"A girl with long legs always has a pair of stockings in her drawer."

I watched as she went to her dresser and pulled out a pair of black stockings. She sat down on her dressing table chair as I stared while she put on the stockings. She bunched up the first one with her fingers and then placed them over her blue nail-polished toes. Heidi slowly pulled them over her foot and past her ankles. She began to straighten her leg as she pulled the stocking over her calf, past her knee, and up her thigh.

Heidi knew she had my undivided attention as she repeated the process with the other stocking. She stood up and pulled them higher on her thighs while straightening them out. I knew she was teasing me and I loved it. She paraded around the room modeling her athletic legs encased in the nylon stockings.

"Well, do you like the stockings?"

"Not really...I love them. You have stunning legs and the stockings make you even sexier than you already are."