Love on the First Date

Story Info
Joel finds true love with petite Tracey on their 1st date.
2.5k words
4.38
29.5k
20
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
BrettJ
BrettJ
4,749 Followers

I certainly did not expect to fall head-over-heels in love with Tracey Wynde on our first date.

The thing about that was that I shouldn't have been on a date with Tracey in the first place. I was still living with Diana and as far as anyone knew, things were fine. A lot of our friends were expecting us to announce our engagement any time soon. We were still having regular sex and going out together and with friends. On the surface, everything was great.

That's all it was –on the surface. The sex that had once been phenomenal was now lackluster. We were still friends and still cared about one another, but I felt as if all of the passion had left our relationship and I think Diana felt it too. Both of us knew we were speeding towards an end, even if neither of us had voiced that opinion as yet.

Before I tell you about Tracey, let me tell you about Diana. She's a gorgeous, curvy, funny lady that is going places. She is well regarded at the newspaper she works for, where she writes articles on the fashion industry. She dresses well and she can dress sexy, she has a body made for sin and isn't afraid to show it off. That's how we met – the company I work for and co-own was doing all of the music for a fashion event. Forget the hot models – one look at Diana and I wanted her. Luckily, we looked good to each other and before a week was over, we were rolling around the sheets and fucking up a storm.

I think that might have been the problem – Diana and I were physically attracted to each other and we really liked each other. We clicked in bed and we clicked as friends, so we thought we should move in together. I think the missing ingredient was love. I loved Diana as a "friend with benefits" and I think she loved me as someone she could take to parties and to dinner and who knew which fork to use for his salad.

I will also admit it didn't hurt my ego to be squiring around a hot, sexy blonde and she was good for business. I know for a fact that a lot of bookings came my way because Diana often came along with me and she loved wearing short skirts when she did and danced all night.

I think that might even have been where I got the first inkling not everything was sunshine and daffodils. I got into DJ work because I love music, but hate dancing. Diana loves to dance and if I wasn't going to join her on the floor or take her dancing, she was going out anyway. Many was the time I would watch the dance floor and see her dancing with some guy, sometimes suggestively, sometimes flirting. Oh, she spent most of the night with me, sharing drinks and laughs, but not enough of it that I didn't have issues with her behavior.

Tracey came along at just the right time to pull me out of the rut in which I was living and to make me see that there was something more out there, that I wanted more in life than Diana could offer me.

Oddly, I met Tracey in much the same way I met Diana. I was working at a local trade show and providing background music and then playing the music for the dance that closed out the show. Tracey was the Events Coordinator.

There was some kind of miscommunication between myself and some of her staff, so Tracey told me that she was coming down to give me her personal assurance that things would be soon be straightened out. I told her over the phone that things would be fine and that was not necessary, but she insisted.

I almost gasped when I saw her face and it was only the beginning. The rest of her body was equally beautiful. I can honestly say that I have never been responded to anyone on a visceral level before the way I did to Tracey – not even Diana.

I know she said something to me, because her lips were moving. I still have no idea what it was; I simply nodded and hoped that I wasn't making a total jackass of myself. She was petite, only 5'1" but she packed a powerful punch.

I have no idea what happened next but she was smiling and I heard her say "yes". It shook me back to reality and I realized that I had just asked her out to dinner. She giggled as she asked me if I wanted to pick her up at her apartment or just meet back here. Still in a fog, I agreed that we should meet back here. I watched her walk away, her hips had that delicious sway I like and she had a great derriere. She was wearing heels and she could walk in them, I find that tremendously sexy.

The staff was riding me all day; they said I was in a really good mood, almost goofy. One of them kidded me that Diana must be planning something special in bed that night. No one knew that Diana was the last person on my mind. All I could think of was sexy little Tracy and what I could do to not make a complete jerk of myself over her.

When Tracey showed up at 7 for our date, I knew that was flat-out impossible.

She had changed her outfit and was now wearing a scandalously short mini that was kind of a burnt sienna color and a blouse that hugged her gorgeous breasts. She was now at least 4 inches taller and wearing shiny, black thigh-high boots with a stiletto tip and also black stockings with a garter-belt barely visible. I am sure I was drooling like an idiot and as she linked her arm through mine, I know my heart was beating a mile a minute.

"I wanted to bring out the sexy for our date tonight," Tracey told me as she stood before me with a smile that would have melted an iceberg. "You like?"

I nodded and tried to think of something to say. My mouth felt as if it was lined with sandpaper but I managed to tell her "You are quite possibly the hottest thing I have ever seen."

That went over well and so did the steak dinner I bought her and the wine and the conversation. She liked that I was interested in her and when she smiled, it lit up the entire room. We went for a walk after and I kept looking at her sexy body and feeling all sorts of carnal urges, but my brain was telling me to take it slow.

Fortunately for me, Tracey didn't give a damn about what my brain thought.

"You're so sexy, Joel," Tracey told me. "I was really into you the moment I laid eyes on you. I like a guy who can wear a suit and honey; you really look good in a suit. I'm going to break my rule for the very first time – if you're feeling the same way I am, take me home, get me out of these clothes andfuck me!"

There was no "if" so I let her know how I was feeling with a really hot kiss; the best I knew how to give. Even in the heels, she had to step up a bit and I couldn't believe how sexy she was. Her dark eyes were looking straight into mine and she held on tight. That gorgeous little body fit against mine like it was meant to be there.

"Fuck," She breathed. "Now I'm even more anxious for you to screw me." She told me the address, it wasn't too far and we got there in record time. She actually tackled me to the floor when we got in her apartment and started taking my clothes off and laughing.

"Hope you don't mind, lover," Tracey laughed. "I'm an aggressive little bitch when I see something I want."

I felt a momentary pang of guilt over what I was doing to Diana, I had never been the type to cheat, but I honestly wanted Tracey more than anything, anyone, in my entire life. I yanked her to me by her long, dark hair and kissed her again. "Why am I the only one getting naked and wouldn't this be more comfortable in a bed?"

"A man who thinks on his feet, wonderful," Tracey smiled down at me while unbuttoning my shirt.

"I'm not exactly on my feet, but thanks," I smiled back as she got up and walked into the bedroom with that sassy walk of hers. I followed close behind and watched her getting undressed. She was flawless, perfect breasts, perfect skin, perfect face. Her lingerie was dainty and sexy and as she went to remove the boots, I put my hand on her shoulder. "Would you mind?" I asked with a huge grin. "I really think those are sexy."

"Ooh, a man who isn't afraid to be a little kinky, nice," Tracey smiled. She licked her lips and said "I happen to agree with you. I have a couple of pair, I thought about wearing the red ones, but I love the heels on these."

"So do I," I beamed at her. Was it possible to be perfectly in sync with a woman? I didn't know yet, but I was hoping to find out. The tiny beauty hopped on the bed and surveyed my body with an appreciative eye.

"Very nice," She smiled, running her hand over my chest. I'm sure I shivered. "I like the salt and pepper hair, I think older men are sexy." She moved her hand towards my cock. "I think this measures up nicely enough, time to do a taste comparison." Tracey bent down and took my cock in her mouth and started sucking. She was all at once fierce and gentle, demanding that I grow and get stiff, yet still swirling and licking and paying dutiful attention to my desires. For once, I held off my own selfish needs and I made sure not to cum in her mouth, although I sure wanted to.

"Marvelous self-control, I'm very impressed," She grinned at me. "I hope you like to eat pussy lover, because I love oral sex. Why do I feel that you probably know what you're doing?"

I grinned. "I don't know? Probably because I do?" I chuckled and set about proving it. Her pussy was prominent, a lovely little pudenda that had been shaved bald and was pink, gleaming with her juices. I began to lick her, massaging her thighs, I felt those sexy boots near my head and ears as I licked. The groove of her cunt was wet with her juices and the aroma was soft and sweet. I concentrated on all aspects of her pussy, not neglecting her clit and making sure I got her off before she rolled away from me.

"Fucking damn!" Tracey panted. "See, that's why I am so into older guys, they not what they're doing and they're considerate," She added. She reached into her nightstand for condoms and put one on me. "I can't believe you're still hard, but after I get you in my pussy, we'll fix that. I hope you don't mind that first time out, I like to top-ride lover. Until I know how well a guy can fuck, I like to call the shots."

"Not a problem," I grinned. I wasn't about to tell her that my balls were aching, but as this sex-hungry cutie mounted me, I saw a look of determination in her eyes. She slithered down on my pole and at first, she took it slow, but when I moved back against her and we got a nice rhythm going, all bets were off. She began giving me the fuck of a lifetime and it was all that I could do to keep up with her. She had gone from sweet young woman to lust-crazed sexpot, swearing and carrying on and having a grand old time. She allowed herself to run free and express her desires, her hands moved all over my body and her long black hair whipped about. I couldn't believe she could fit my cock inside of her snug little pussy, but she sure as hell did and gave me one hell of a workout.

She kept going "uh uh UH" as she thrust herself hard against me and when she was close to coming, I saw a little wince cross her face and the "uh" turned to "aahhhh". Her body relaxed and a serene look crossed her face. She looked down at me and smiled and then her face took on a quizzical expression.

"You didn't cum YET?" Tracey asked me. I shook my head and smiled at her.

"I wanted you to cum first, if I want to keep the lady coming back for more, got to take good care of her," I said.

"Oh, I amdefinitely coming back for more, but I amnot going to be a lady about it," Tracey sighed. She got on all fours and wiggled a delicious ass at me. "I saw you checking out my ass earlier, fuck me from behind and be a bit rough, spank me or pull my hair, use me like your own personal little slut!"

I liked that Tracey could be smart and clever and funny, but let loose in the bedroom. I liked it a LOT and so I made sure to deliver just what she asked. I fucked her from behind and really drilled her, screwing her until she whimpered and cried and begged for more. Her exquisite tears finally sent me over the brink and I filled the condom with my spunk.

We fucked one more time that evening before I went home. Diana wasn't there and I had absolutely no idea where the hell she was. I suppose I should have been angry and I was expecting a big confrontation. That came a few days later, but in a way I never expected.

Diana had found a new apartment and was moving out. She told me neither of us was moving forward, we were just standing still and stagnating. She was kind about it, told me she cared for me, but we were in need of other things. I offered to help her pack up and move, but she had hired movers and would be gone on the weekend.

I didn't confess my infidelity to her, there was no need. I had one order of business to attend to. I got out my cell and dialed Tracey's number. When she heard my voice, her entire manner changed, she was flirty and bubbly, like I mattered. It was exactly what I wanted in my life, what I truly needed in my life. I invited her to dinner and hoped that I could convince her that I wasn't insane for falling in love with her on our first date.

She accepted and I convinced her that night –four times. We're getting married in a few months and both looking forward to spending the rest of our lives together. Of course, there are a few small details of our courtship we won't be sharing with our kids.

BrettJ
BrettJ
4,749 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Nothing Between Us Two friends let it happen.in First Time
Sales Team Desperate woman tries to pay back man who saves her.in Romance
Poolboy Benefits She's desperate for help. The question is, how desperate?in Romance
Hero's Reward One brave deed holds the key to unlocking a scarred heart.in Romance
Charity Begins Next Door Life isn't fair. So when you fight back, fight dirty.in Romance
More Stories