Church Boy - Backstory

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The stories behind the series.
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Part 2 of the 5 part series

Updated 06/09/2023
Created 10/23/2019
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When I was younger I used to keep journals. They're filled with significant events and things I would have otherwise forgotten the details of. Of course, most of the things I wrote in them were related to sex (first blowjob, best or worst blowjob, etc.). I was reading and reminiscing about some of my sexual adventures (and "misadventures") and one of the results is a series I wrote called "Church Boy". The basis of which are actual people and events, embellished with "wished this would have happened too".

I still find it ironic that my earliest sexual experiences are associated with the church I attended when I was growing up. Especially since my VERY "church-lady-ish" mother thought it would be a good idea to keep me as close to the church as possible to cull any mischievous, sexual notions or intentions I might have had. She never took into account the "notions and intentions" of some of the other "church ladies".

Ha!

In the first "Church Boy" story, the main character, Brian, ("me") is a young man that has a sexual encounter with an older woman, Lydia, while traveling home on a bus from a church sponsored getaway.

This actually did happen to me. This was during the summer after my freshman year. I was around 19 or 20, and LM (her real initials) was 35. Both of us were flirting throughout the entire trip, which took place over the course of 4-days. This culminated in us making out one night, and then me fingering and going down on her during the return trip.

Unfortunately, that was also the only time that LM and I would get together. She had a live-in boyfriend. We certainly tried to hook up - multiple times - but it never happened. In the second story I imagined what getting together with her might have been like, and in part four I imagined a threesome with LM and another lady from church that I'd had encounters with.

In part three of the series, I introduce Willimena, or "Miss Willie". LW (actual initials) was also an actual person. She was a close friend of my grandmother. They'd served on several administrative committees together. I also recall that she and my mother didn't really like each other (although it was mostly my mother that had an issue).

We had several dozen causal encounters from the time I was 20 that lasted until I was 22 when I moved away from home. At the time she was in her mid to late 50s. She was also the first person to tell me "there's NOTHING WRONG" with sex - it's fun and feels good for a REASON! I personally credit LW with being responsible for my sexual enlightenment, growth and creativity. She was a VERY open-minded lady!

LW was a woman who followed her own path, she was flirtatious, and always had a nick-name for people she liked (she called me "Sweetie"). She was into yoga and was the first to laugh at (or tell) "off-color" humor. She was also the first person her age I'd met that had tattoos (peace-sign on left shoulder, Black-Power fist and a heart at top of left thigh).

The definite polar opposite of my mother.

I'd have to "blame" my grandmother for LW and me first getting together. As I got older, Grandma would sometimes use me as her courier to retrieve or drop off church documents at LW's apartment. I think she also did this to get me out of the house and away from my mother's barrage of "you're not amounting to shit" attacks.

Thanks Grandma!

LW lived about 40 minutes (walking) from our house, in a neighborhood where some of my friends from school lived. Later when I was questioned as to my whereabouts, I would use "hangin' with TJ" or "at Donald's house" as an excuse (the three of us had a long-standing alibi pact).

The first time "things got started" with LW, I was dropping off some church paperwork. I'd done this several times before, which meant waiting around to bring something back to Grandma or she'd offer me something to eat. Once we just sat and watched a college football game.

This time she just wanted to chat, but this was also one of those times she was practicing yoga. This wasn't the first time I'd seen her doing yoga, stretching and bending, wearing a leotard and barefoot, but this time I was a horny 20-year-old. I was a lot more confident and forward with my "notions" and was very open with sharing them. I wrote a re-imaging of watching her go through her yoga routine in the 3rd chapter of "Church Boy" - very similar to what actually happened - staring at breasts and protruding nipples, resulting in an obvious raging hard-on.

The next time I went to see LW was at her invitation. She wanted to talk and "hang out", so we ended up watching TV and having take-out and cheap wine. She asked me to rub and oil her feet, which I did - resulting in more raging hard-on. She suggested I go into the bathroom and relieve myself - I did. That facilitated our first kiss and lots of touching afterwards. She let me put my hand between her legs ("up the skirt but over the panties") and rub her off.

I was back at her place a few days later. When I went over this time (late afternoon) she answered the door wearing only a silk robe and a nightshirt. The next several hours were spent having my first ever lesson on "the art of cunnilingus".

Those "lessons" lasted almost 2 years. Every woman I've been with since owes LW a debt!

Some of the most memorable things we tried included:

*mutual masturbation

*nipple tease orgasms

*role play (her favorites were "teacher and student", "step-mom" and "the landlady")

*anal and anilingus

*bondage

*public sex (we were almost caught in the Uptown Theater in DC!)

*our first swing parties (those parties resulted in both good and bad experiences)

We'd get together 2 to 3 times a month. With each visit she seemed to want to try or teach me something new. LW admitted that many of the things we did she'd always wanted to try but could never find a willing or available partner.

Our arrangement remained our special secret.

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KlitomaticKlitomaticover 3 years ago
My Older Woman

Was Jeanie, a 32 yr old English woman proud of her Cockney accent. I was her boy toy, and she used me relentlessly and well. Like you, the women I've been with since have her to thank for any sexual talent I might have.

grayge37grayge37over 3 years ago

Very helpful in getting me to read your material. Did not need a vote, but I gave it a four just to keep up your average.

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Church Boy Previous Part
Church Boy Series Info

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