Confessions Of A Serial Dater

Since 2000, which coincidently was the magical year my marriage ended, I've had the pleasure and in a lot of cases displeasure of dating a multitude of women spanning quite a few east coast (and one midwest) states. Those dates remain as memories forever etched in the dark annals of my mind. This is my forum for which I will share the best of those dates....These are the confessions of a serial dater.

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Location: Washington, DC, United States

Edward Bernays would dig me. Seasoned public relations strategist (10+ years in the game) who has practiced PR in multiple cities: Baltimore, Detroit, Chicago & DC. I'm an observationist and a soon to be card carrying member of the Twitterati. I love comfortable silences, revel in the Seinfeldian absurdities of life and have been described as a habitual line stepper. These are my thoughts...

Monday, July 31, 2006

WHEN I WAS 17

I Know, I know…this has become a bad habit (lol). My apologies to all for my hiatus, but bare with me it’s summer time and during summer time there’s lots to do, people to see (where else would I get material from) and places to go. Most recently, one such place was my hometown of Baltimore, Maryland.

During my recent sabbatical to B-More, it got me to thinking about growing up and some of the experiences I’ve had. Back when I was 17, I was obsessed with getting girls (not that much different from now at age 35 – but with less emphasis on the obsessing thing). I was completely girl crazy. And it would seem like every other month I would be infatuated with a new object of my desire. At the time of this particular recollection, I was infatuated with a junior hottie at my high school named Ingrid.

Ingrid was not by far the most beautiful or the most popular girl in my high school. However she was the captain of the cheerleader squad, had long dark hair, deep dimples that seemed to suck you in when she smiled and was sorta on the thick side (with a bodacious booty you could literally set a drink on). She was also attractive and had an infectious laugh that made you laugh too when you heard it. I wanted her sexy five-foot ass from the moment I first saw her in the hallways at school. I just wasn’t quite sure how to go about getting her. Back then, I wasn’t quite the calculating aggressor I am today, so I had to come up with a game plan to win her over.

Once upon a time I used to belong to an after school club called FBLA (Future Business Leaders of America). I used to participate in economics competitions and the whole nine. One time, as a project, we formed a company and the product was teddy bears. We had to order and sell these teddy bears like we were running an actual business. While I was involved with this project, I found a way to order some additional bears at no cost, so we had some overstock. I used to sell that overstock to hustle a lil extra money on the side or I’d give the bears away to pretty girls I liked.

One day I cut class and went to one of the later lunch periods that Ingrid was on. While she was my sole reason for being there, I pretended to bump into her as a chance meeting and because she was “so pretty” I gave her a bear. Not the smoothest scenario I could’ve come up with, but it allowed me to get some face time with her and at least let her know I existed. While the free teddy bear didn’t exactly net me some nookie or a phone number we did exchange names and smiles.

One of my boys noticed that I was all up in Ingrid’s grill, so he gave me a lil bit useful information. He let me know where she lived. Ingrid was a neighborhood girl. While she didn’t live in my neighborhood, she did live in a nearby neighborhood that I’d recently started hanging out in. So one day I get the ambitious idea to go knock on her door and just kick the Willie Bo Bo. I hopped on my bike (wasn’t pushin the Green Machine back then) and rode to her hood.

I dropped my bike off at the foot her porch and walks up to ring the doorbell after mustering up the courage. That’s when a female’s voice called out from behind me.

Ms. High School Honey: “S’cuse me. Who you looking for?”

SD: “I’m here to see Ingrid.”

Ms. High School Honey: “Ingrid huh? She’s not there.”

SD: “You know when she coming back?”

Ms. High School Honey: “How come you’re not here to see me?”


I turned around and whadda you know. At first all I saw were ass and thighs, then I panned up and saw her face – Pretty. “Ingrid who?” I thought to myself. I left the porch to go talk to the pretty girl standing across the street in front of Ingrid’s house.

SD: “You know Ingrid?”

Ms. High School Honey: “I should know her, she my sister.”

Whoa!

SD: “I never knew she had a cute younger sister. You go to school up the ‘The Park’?”

Ms. High School Honey: “Yes, this my first year there. So you think I’m cute huh?”

SD: “Definitely.”

Ms. High School Honey: “Well I’ve seen you before and I think you’re cute too.”

SD: “Oh yeah. Well my name is Serial.”

Ms. High School Honey: “Nice to meet you Serial, my name is Crystal.” {smiles}


From the moment of that unexpected meeting with Ms. Crystal (henceforth known as Ms. High School Honey), I never thought about hooking up with Ingrid again. As a matter of fact we started talkin’ and eventually officially became a couple. I never did fess up to liking Ingrid and it was weird being over their house chillin’ with the three of them (Ms. High School Honey was a fraternal twin) knowing that I used to lust after my girl’s big sister.

Ms. High School Honey and I stayed a couple all the way through the end of my first semester of college, which was roughly just short of a year in length. Once I got to college, I didn’t want a whole lot to do with high school girls. They were just too young for me I thought. But I won’t blame college or me living on campus for Ms. High School Honey and I breaking up. Sometimes distance creates separation. And sometimes separation creates opportunities for cheating.

I got a kite from a homey of mine one time, telling me to check my girl back home. He informed me that everything wasn’t sweet. I didn’t blame her for straying, I was in college doing my Serial Dating thing. So I expected some repercussions. Her infidelity gave me just cause to do what I wanted to do anyway – break up with her. So we split in mutual agreement. {Side note: Ingrid wound up attending my college and when she got there, she told everyone that she was my sister. So for about three years I had a little sister on campus – go figure.}

Here’s the kicker about the Ms. High School Honey and I situation…she was a bonafied virgin when I met her. At the time she was only a freshman and I was senior at our high school. And lord knows I wasn’t tryna let her remain a virgin – hell not on my watch! But atlas I couldn’t get the draws. She stonewalled me at every turn. Yeah I sucked some titties and fingered her a few times but it never went beyond that or tongue kissing. And back then black women weren’t giving head, so I took a loss with that one.

Flash Forward (10 plus years later)

So I’m on Black Planet one day, just fucking around online and I get a note from a woman with no pic on her page. “Here we go again with the fatty ugmoes,” I say to myself. Turns out that this particular ugmoe was none other than my college sister – Ingrid. We chat it up a bit in our note exchanges. But before she signs off, she types, “Oh yeah, Chrys got a page on her too.” I ask her for Ms. High School Honey’s BP screen name and look her up. Sho enough there she is on my screen with a picture on her BP page and looking as cute as she did when I first met her.

Of course she’s in her 30’s at this point, three rug rats deep and little on the 12-14 size. I hit her up and we began a dialogue. Turns out she’s up for seeing the Serial one again after all these years. We exchange phone numbers and make plans for me to slide through her spot and visit. As luck would have it, she only lived about 10 minutes away from where I was staying. What were the chances?

On my first visit, which was late night after her brood had hit the hay, we just kicked it talking and watching a movie together. I wanted to make a move, but I didn’t think that opportunity presented itself. So I chilled laying in the cut for another chance. That chance would come on my second visit. Again I came over after the little ones were laid to rest. As opposed to sitting out in the living room watching TV, we sat in her room, on her bed with the door closed. If that wasn’t a set up, I don’t know what is.

We started out watching TV, but one thing led to another, which led to some deep passionate tongue kissing, which led to a Lifestyle packet getting ripped open, which then led to a pretty mom of three with a dick up in her. As I penetrated her, I couldn’t believe that after nearly 15 years we were finally doing the nasty. And once the realization hit home that we were, I made the most of it. I pounded her ass something fierce. We talking more than a decade of waiting for that moment. On top, from the side, from behind, I made it count until she exploded and damn near passed out. I felt really good about the situation. ;o)

Ms. High School Honey: “So tell me Serial, was it worth the wait?” {sounding winded and satisfied}

Serial Dater: “You damn right it was worth it.”

(Ms. High School Honey crossed off the list)


Yeah I’d say it was worth the wait. ;o)

25 Comments:

Blogger In Denial Hoe said...

Well let me be the first to say "It’s sooo nice to have you back" Enjoyed the story. . .pull that one myself “holding out” (I know IDH yeah right?) but surprisingly when I did let him hit it Damn if my poor of kitty did not pay the price. Best Sex I ever had. Thanks!!

8:21 AM  
Blogger BZ said...

Good story and very cute. Reminds of my HS boyfriend. I was a virgin and didn't let him hit it until my sophomore year in college when I finally wanted to lose my virginity. Ahhh, Thanksgiving Break 1995. And oh yeah, glad I waited! HAHAHA

9:32 AM  
Blogger TTD said...

you & these breaks need to come to an end dammit! this story was so sweet! nice to see that you didnt dump her for being a virgin!

10:18 AM  
Blogger The_Practitioner said...

ID Hoe - Welcum. I breifly scanned your stuff. Imma have to start checkin you out.

BZ - Always give up. It makes the world a better place

TTD - I didn't mind the Virgin thing so much. I was doing my thing on the side and Ms High School Honey was attractive to boot, so I got nuff props in the neighborhood. Besides everybody thought I was hittin it anyway. What did I care if it wasn't true. ;o)

10:34 AM  
Anonymous Anonymous said...

Cute story....I always wondered why the longer you make him wait....the more he tries to break your back ;-) LOL

11:38 AM  
Anonymous Anonymous said...

Glad to see that you have returned with a good adventure.

I dont know if there are any high school females I would mess with now. Ok, maybe one. But there are not that many.

12:03 PM  
Blogger aquababie said...

i was wondering what happened to you. glad you're back. that was a very sweet story. made me all fluttery in my tummy. LOL

1:57 PM  
Blogger Prophetess said...

Well, hell, Bro. Serial, you coulda fucked Ingrid, too. I suspect Ingrid wouldn't have told it.

You're right; it's hotna bitch these days. You think its hot where you are; try 15+ days of 100+ temps everyday. That's what we dealing with in Texas (Big D).

Glad to see you back, Serial.

7:32 PM  
Blogger Tenacious said...

cute story :-)

I really enjoyed this one.

Thanks for stopping by :-)

12:18 AM  
Blogger Mahogany Misfit said...

Welcome back my favorite Serial Dater!

This was a really good post and I am LMAO @ "And lord knows I wasn’t tryna let her remain a virgin – hell not on my watch!"

That is too funny!!!!!!!!

1:02 AM  
Blogger The_Practitioner said...

Normally, I'd toss up two sisters in a heartbeat. But I was a little to close to this family and one was actually a girlfriend. So I got rules about stuff like that.

3:23 PM  
Blogger journiemajor said...

Welcome back boo!!!!! Great story, as usual, but keep them comin.

3:40 PM  
Blogger Nika Laqui said...

*lol* Dang, 15 years....


Hell you haven't blogged for about 15 years, so it was worth the wait...

3:59 PM  
Blogger Freaky Deaky said...

Nice post SD, welcome back!

4:03 PM  
Anonymous Anonymous said...

You and these hiatuses have to stop. At least give a warning when you're MIA or something.

7:32 PM  
Blogger Remnants of U said...

Great story! Glad that you are back!

8:31 PM  
Blogger Ms.Honey said...

LOL all I got to say is I'm glad you back and you need to stop leaving us hanging for so long LOL

I had one like that..never did let hit and finally he did (we'd been "dating" since middle school) boy after the first and second time he wouldn't leave me alone LOL...I know consider him a lil brother LOL..funny

9:01 PM  
Blogger Chubby Chocolate said...

I swear the first half of this story was like some after school special.


If you were that much of a creative mack back then, you should by now already have honed your skill and able to get the panties without them even realizing they gave it up. LOL!!!

2:24 AM  
Blogger EqualOpportunityCrush said...

i was thinking that you woulda ended up hitting Ingrid off too..lol.. good story nonetheless.. funny I have a high school sweetheart coming after me right now and it's been over a decade.. but that nigga ain't crossing me off his list! lol.. we were together when we were both virgins.. and that's all he's gonna have to keep remembering! lol

3:52 AM  
Blogger The_Practitioner said...

RESPONSE RUN DOWN:

To all that welcomed me back - Great to be back; I been busy for a minute

nsane - I answered your question in the close of the story

Funky - The boning took place nearly three years ago and then I moved to Michigan. Haven't seen her since I been here

Chubster - I do get the panties without either one of realizing it (lol)

Equal - Gwon a give the lil nigga a taste. ;o)

I'll try not to leave ya'll hangin' so long next time. I already got a couple of "bangers" in the chamber.

I'm seriously smellin' a book deal in the works.

11:17 AM  
Blogger Debi the Matchmaker said...

If you met a girl who won her Super Bowl pool four years running and was great at Holdem' would you consider committment?

debi
www.PricelessIntroductions.com

10:34 PM  
Anonymous Anonymous said...

Wow, these could all be my stories.

2:11 PM  
Anonymous Anonymous said...

SERIAL WTF ARE YOU/HAVE YOU BEEN?

5:16 PM  
Anonymous goophus said...

Great story....very entertaining!

11:41 PM  
Anonymous bennie efemena ben-iriri said...

Great story;glad you are back.So what is the update?

8:10 AM  

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