Billie's Business Box

by Tony Tiger

Copyright© 2019 by Tony Tiger

Romantic Sex Story: I reconnect with a woman whose cherry I took in high school. Catching up with the five years since then is delightful and surprising, especially with her career.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Sharing   Pregnancy   Prostitution   .

As soon as I bumped into Billie at the grocery store I asked her out, hoping she wasn’t involved with a guy. She seemed really tickled to see me after such a long time. I’d just moved back to our home town and hadn’t reconnected with very many yet.

We went to the restored small town theatre where we dated back in high school after a dinner at a restaurant still run by the same family. What nostalgia! It had been five years and I’d been in lots of places around the world and decided to take some time off. Being a self-employed contractor made that a lot easier.

Back to the date. Billie was looking real good, her red hair was nicely done and she dressed and behaved well, not that she didn’t way back when. At the end of the evening she surprised me. “Tony, I’d like to see what time has done for the man I’ll never forget.” That was because I took her cherry when she was a junior and I was a senior. I picked up on the self-invitation to my bed and guided her to it.

“Damn,” I thought, “Five years has certainly made her better looking. Has it done the same for her fucking? I’m gonna find out.”

It’s difficult to remember details over that length of time but she sure as a first-class piece tonight and seemed to be really enjoying what I was contributing too. We’d dated pretty intensively for two months until school was out and I had an out-of-town special summer class. When I got back I was immersed in my new job and she was dating other high-school guys. Since this work had me away a lot we never picked up where we left off.

Tonight she held me close as our passion settled down. “Mmmm! Loved it and so glad you are back”, I heard from this love-bunny.

I had some more intimate questions now. “I take it you’re not committed to anyone. Do you date much?”

She looked at me intently, “Do you wanna know?”

I gulped, “Yeah. I think honesty is the best way to go.”

She relaxed, “Well, it’s not that easy to explain. This is the first conventional ‘date’ I’ve had in a long time but not the first sex. Are you SURE you want to know? It may not be what you expect.” I nodded. “Maybe if I fill you in about my life since we parted you will understand it better.”

I interrupted, “How about we fix some drinks and get comfortable. Sounds like I might get reloaded during this so I hope you can handle more coupling.” It was her turn to grin and nod.

“After we split I moped for awhile and then accepted some date invitations. When I finally took my clothes off with one guy it started a series of new acquaintances and lovers. Again, I thank you for showing me how to screw well and wising me up to birth control. That kept me from birthing a passel of assorted kids. I didn’t get feeling special along for any of these guys in my head like I did you but the lower connections were interesting and kept my horns clipped.

“I took a good job in the city because none around here were. The train made it easy to commute and I got my own little apartment not too far from yours. The money was good too as an administrative assistant. After six months my boss took me out to dinner and proposed a promotion. I was smart, attractive, and had the right personality. This business did a lot of big sales as a supplier and most of the buyers were male. The woman who had helped close many of the best deals had retired and he wanted to offer that position to me.

“Turns out that taking clothes off and what usually follows was an important selling tool. The boss also wanted to do twice weekly ‘quality control’ on what I would deliver. He was OK so that wasn’t an issue. The salary was more than doubling what I got then and with bonuses for successful sales, could put me into six digits. Shit! Never thought I’d earn that or be a prostitute either, although the fancy title was ‘escort’!

“Any questions so far?”

I was hard again and slid into her already lubed place with little effort. She smiled and squeezed me with talented and trained muscles.

“So there have been lots of cocks where you are now and never a complaint because of that. Good sales results actually. I do want you to know that I am an actress for those encounters and don’t get the satisfaction that voluntarily doing a guy I like, like right now, can deliver.

I was moving in this talented twat and interrupted her talk with a big kiss, then said, “Enough for now. My sex life has been rather boring compared to yours. You are improving it a lot so let’s focus on it right now.” We did but then she said she had to get up early in the morning so needed me to take her home. I asked about our next date and she checked on her phone.

“I’m going to be travelling all of next week. There is a big trade show that we do every year. I’ll let you know when we can get together as soon as I know.” I got a fervent kiss that I was told her “customers” didn’t.

Early Thursday evening I got a call from Billie, “Can you pick me up at the airport at four tomorrow? If you can allocate the rest of tomorrow and at least the morning Saturday I’d really appreciate it.” You bet I could!

She didn’t want to talk much on the trip to her place and when we got there she poured us drinks and sat on the couch, still clothed. Probably had a lot to do with her “work” at that show.

Finally she spoke, “I did a lot of thinking on the way back. This show seemed different than the others I’ve been to. Fucking at those was kind of an adventure but this time it was a chore. I think that means I need to make a change. Yes, it’s your fault! Well, sort of anyway. You’ve helped me deal with feelings for a man and I realized how much I’d been missing them since we were together long ago.” I just listened intently and nodded when appropriate.

“Speaking of feelings, I’ve been wondering how you can accept me as a girlfriend when I just got laid by five guys over five days for a total of nineteen times. That’s left me a bit sore in my lower lips but my upper ones would be happy to release any accumulated sex tension, unless you found another outlet.” She looked at me a bit quizzically. I didn’t respond either way so she knelt down and unzipped my pants, looking up At my face as she did what she had offered.

When she got a mouthful I pulled her up and gave her a closed-mouth kiss, “That felt good and now I know why you wanted to stay until tomorrow. Me too.”

We did a lot of talking that night. She had saved two-thirds of her large income and wanted to get her Associate degree at the community college so she could get a good job where she left her panties on, although she did like going commando sometimes.

I made a bold suggestion. “This is a pretty big apartment. Do you think there would be space for a roommate who would save you half the rent and utilities plus maybe other things?”

Her jaw dropped, “OMG, I never expected that! I also never expected a man to want to live with a slut like me. Of course I want it, but when?”

“My rent is month to month so it should be done about the time you give some notice. My apartment is furnished so moving will be easy unless I need to find another bed.”

“You better be kidding, big boy. Do you want me to replace the mattress to clean out the many memories that have happened there?”

I looked her square in the face, “We are not married or even engaged so I can pose no restrictions. If you need privacy for a bed visitor just let me know and I’ll do the same. Fair enough?” She wasn’t sure just where I was coming from so nodded. A topic for further discussion I thought.

There is more of this story...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.