Chapter 9: Engagement

Friday, late afternoon, Lindsay arrived. I picked her up at the airport and she was all over me with a lot of PDAs right beside the luggage carousel in the terminal building as we waited for her giant backpack to appear. I brought her home to my apartment, explaining about what Greg and Sandy were going through with their parents as part of a ruse to deflect their thinking away from anything incestuous between them.

Sarah didn’t get home from work until nearly seven o’clock. She was having some sort of financial crisis at Jaycor and had a long work session rather than calling people in to work over the weekend. She found Lindsay and me on her sofa making out, but we both turned our attentions on her and gave her a heavy dose of love,

Sarah, Lindsay, and I went to a late dinner at Patrick’s. I got my hit of red meat for the day, and then we went home and I think I made the two of them happy with lots of loving, orgasms, and sex play. Lindsay told us about her recent filming endeavors using crude terms that she knew would excite us – me more than Sarah.

We ran on Saturday morning, but in deference to Lindsay, we trimmed the run to eight miles at a slower pace than Sarah and I normally did. I loved that Sarah enjoyed the long runs. I loved everything about Sarah. Just thinking about her made my heart beat faster and made all sorts of love chemicals and hormones explode in my body.

We stopped for breakfast at The Station again. After some talk about the sights that we’d passed during the run, Lindsay turned to her sister, “Hey, sis. The studio guys want me to make you an offer you can’t refuse to come down to Miami and make a movie and two shorts. One week of work for $12,000.”

Sarah shot me a glance and then said to Lindsay, “You know I’m not in that business any more. Tell them that I appreciate the generous offer, but I have a new life that doesn’t include that stuff regardless of the pay. Attractive offer, though.”

Lindsay gestured at me, “They said that if you had a boyfriend, you could bring him and they’d put him in the films. One grand a day for him.”

Sarah kept shaking her head. “No, no, no. I’m not even tempted.”

“Why?” Lindsay asked.

Sarah looked at me but talked to her sister. “I had a good run at the porn, but when I looked around at the characters that I wanted with me the rest of my life, there wasn’t one – not one. The men were either sleazy assholes or just not my type, and unless there’s been some kind of time warp, they still are. I was in the business for over ten years and from year-to-year that opinion didn’t change. I did okay and made some friends, but nothing really long-term that was male.

“I saved up and invested my money. I’d had a lot of great advice, fortunately. Some of my escort clients were nice, but I know what I was to them – a pretty whore. I created a financial cushion and got an education. I decided to use the latter and get a job that will last me for a long time with people that I like.

“In the process, I moved into the right building and from next door met the most wonderful man in the world – Doug. He loves me and I love him with every fiber in my being. He’s even willing to allow me the freedom and flexibility to enjoy some other dick once in a while. Of course, I give him that same privilege, as you well know.” She grinned and giggled.

Sarah went on, “Any way, I am hoping that Doug will propose something permanent someday. Also, sometime soon, I’m going to have to meet his parents and pass muster as ‘acceptable’. To be honest with them, we’ve agreed that I’ll tell them about my past career rather than let them discover it some other way. They most likely won’t like it, but I hope they will tolerate me because it is in the past, because I dearly love their son, and because I have made what looks like a successful career transition. I don’t want to do anything that screws up that transition. I’ve promised myself.”

Lindsay grinned, “Good. I told them there was no hope, but I did say that I’d ask. I’m glad for you and your firm stance. Sometime soon, you’ll be my role model for quitting the sex industry. I’m also grateful to you for sharing Doug with me once in a while.” She leaned over on the sofa and kissed me. I kissed back.

I felt that I had to respond to what Sarah had said. I started slowly, organizing my thoughts as I started. “Sarah, I do want something permanent and long-term with you – like getting engaged and then married. Just to reiterate, what my parents say or don’t say about your past will have little bearing on us. I’m pretty sure they’ll ask a few questions, and then forget it; I think they’re pretty forgiving about that kind of stuff. Also, I don’t want to wait too long for us to change our status.”

Lindsay shot up and did a happy dance in place. “Yeah. If you’re going to propose, which you almost did. Will you do it while I’m here?” She looked hopeful.

Sarah and I laughed. I said, “Maybe.”

We introduced Lindsay to Tom and Marie – Greg and Sandy’s parents – at lunch the next day. We all behaved and didn’t do any revealing or teasing of note. Greg and Sandy’s parents had a late-afternoon flight north. Lindsay was staying for the week for some R&R from her fucking job – literally.

Sarah, Lindsay, and I took a long walk to dinner at the Cantina – a Tex-Mex place with good food, but loud entertainment. We were lucky enough to get a table on the far side of the restaurant away from the one-man band. He was making up for a lack of talent with volume.

Over dinner, I asked Sarah, “Do you think that it takes any of the luster and excitement away from a proposal if the couple have picked out the engagement ring ahead of time?”

Sarah grinned and shook her head. “In the interest of getting the right ring that’ll be on display on my finger for the next sixty years or more, I have to say no.”

I admitted that those were my feelings, too. I then asked, “Might you have some time this week to go shopping up in the Tampa jewelry district. Some of my co-workers suggested that was the best place in the state to buy a diamond. I assume you want a diamond?”

Sarah laughed, “A girl’s best friend, you know.”

“How about Wednesday afternoon?”

“Yes. I’ll move whatever I have to for these life-changing moments.” She smiled.

I said to Lindsay, “As much as this has to do with Sarah and me, you are welcome to come with us. And just so you all know, after we pick a ring, I will then wait for an appropriate occasion to get down on bended knee and formalize things.”

Sarah acknowledged, “Great. My heart is already soaring with joy about our future together.” I could tell that she was walking about three feet off the ground and her smile lit up whatever room we were in. Lindsay looked very happy for her sister.

I was with the two of them that night, and did my best to make both of them happy and sexually sated. The next two days were a blur at work. I squeezed in some time with my A.I. software asking about diamonds and got a good education about the subject and about prices.

Wednesday, I collected Lindsay and Sarah at noon, and we drove the hour’s ride to Tampa, stopping for a fast-food lunch along the way. We went to four stores. By four o’clock, I had a blue velvet box in a small bag that contained a beautiful diamond ring – almost two carats, with two Baguettes on either side in an ornate platinum setting. Sarah was beside herself with expectation. She twitched for the entire ride back to Sarasota and kept looking at the bag that Lindsay was carrying as she sat in the backseat.

That night, I called home just after dinner to FaceTime with my parents. Sarah was with me and I introduced her to them as ‘the most special person in my life’. They’d heard me talk about her in other conversations, but this was the first face-to-face contact. Also, my father sometimes introduced my mother that way – ‘the most special person in my life’ – so they knew instantly that I was sending a coded message that we were quite serious about our relationship. Everyone was very polite. We did not mention Sarah’s porn and escort career.

After we ended the call, I texted my dad that I’d bought an engagement ring that afternoon and planned on popping the questions very soon. I also asked whether we could come and visit in about ten days for a three-day weekend.

I got back a huge smiley face and the invitation to come and to please bring Sarah. I told Sarah our plans and she got so nervous I thought she’d expire on the spot. Lindsay and I calmed her down with a massage and some herbal tea. Later, we calmed her further with two orgasms, one rendered by her sister and the other by me.

Friday night, the seven of us went out to dinner, and then had a really good orgy in Sarah’s living room. Both Jon and Greg wanted to nail Lindsay, and the feeling was mutual. Except for Sarah, the new members of our group were also curious about the Miami porn star, a.k.a. Sarah’s sister.

We happily played the rotation game, switching partners every five minutes. We were all naked, and after nearly an hour of fucking, every guy had had their cock in every female body at least a couple of times in different positions. One by one, despite efforts to extend, the male orgasms started to occur, and then there was licking and sucking of pussies, and then there were drinks and a refresh period.

When we were all back sitting around naked, kind of waiting for Round 2 to start, I got down on one knee in front of Sarah and proposed that we become engaged to be married. She squealed. I produced the ring box from under the sofa, and slipped the ring on her hand. It was a perfect fit. Duh!

There was laughter as everyone talked about how unconventional the proposal was. I was naked and so was Sarah; I’d just fucked Lindsay – my new fiancée’s sister; I had the juices from four women fresh on my cock; there were five other naked people in the room; we were all getting ready to fuck again; my new fiancée had cum or pre-cum in her pussy from the three men present, all whom were going to fuck her again over the next hour.

There was a period where the ring was the most important thing in the room, and then Sarah urged that we start Round 2. She went for me, but I knew that in our rotation Jon should be with her. I joined the two of them, and kissed Sarah and then gave her a wink. She was obviously thriving on how mischievously we were behaving as a newly engaged couple. God, she was sexy. I was engaged to the porn star next door!

Later, she said, “I wonder how many girls get proposed to and engaged while they’re in the middle of a group sex orgy?”

We repeated our seven-person orgy on Saturday night after spending the afternoon at the clothing-optional beach. I actually fucked her while we were at the beach and somewhat hidden by the other people in our group and two of our beach umbrellas.

Sunday, I dropped off Lindsay at the passenger terminal, and drove around to the other side of the airport. I spent the day there and took two flying lessons about two hours apart. In between the flying lessons, I had ground school, studying air traffic rules and FAA regulations. I’d missed a few weeks and my first lesson that day proved to me that I could easily get rusty about this hobby.

Sunday night, we were back in orgy mode, but being a night before a work day, the six of us didn’t go late, but we each got in some loving with every one of the opposite sex.

The week was unique in that I moved up, it seemed, in the eyes of my colleagues because I’d gotten engaged. I was aided in my new friendships by two photos that I’d taken at the beach, printed, and framed for my desk: one was a close-up of Sarah in her mini-bikini smiling at the camera, and the other was a photo of Sarah, Lindsay, Sandy, and Rachel in their bathing suits mugging for the camera with Jon and Greg behind them with big smiles. There was a lot of flesh showing, and my work mates liked my selection of pictures. I think I had visitors to my cubicle just to gander another look at the pin-ups. To my knowledge, no one had recognized Sarah as Candy Sweet.

Sarah and I prepped all week to get ready for our trip to Charlotte, North Carolina, and then the drive west to my parents’ home. We were leaving Sarasota on a three o’clock flight, so the afternoon was blown. She was as nervous as a long-tailed cat in a room of rocking chairs. I kept calming her.

She kept wanting to rehearse her ‘reveal’ about her past work in pornography, trying different approaches and talking about different levels of involvement. I urged her to tell the whole story and to not hold back. I didn’t like to receive information about a subject in dribs and drabs over days, weeks, or months, and I was sure my parents were the same way.

I reminded her that even if they didn’t love her, that I did and that was all that counted. She, on the other hand, wanted a nice ‘daughter-in-law’ relationship with them. Since her own family had fallen apart with absentee and uncaring parents much of the time, she wanted something more substantial in her adult life.

My parents had a house on a small man-made lake. Both of them worked near Charlotte: mom as a part-time paralegal and dad as the owner-manager of an independent motel at one of the exits off Interstate 85 – a short distance from the house. They were both in their early fifties and going strong. Mom did yoga and dad was a jogger, like me. I think both of them weighed about what they did in high school; a healthy life style was important to each of them.

We arrived at the house just after six o’clock. There were welcoming hugs and kisses, and Sarah and her new engagement ring then got all the attention. I was pleased how they fawned over her. She easily responded about how we met: moved in next door to Doug and then we found out that we were both serious joggers and so we started to run together, which led to coffee together, which led to more talking and then dates. Sarah kept her descriptions G-rated.

My mother, Dot, made a point of getting Sarah to call her Dot or Mom. My dad went along with that with her as Jim or Dad. They were pretty informal about this kind of thing. I’d even called my mother Dot sometimes as I grew up. The both had a young attitude about life and other people.

My mom must have come home early from work, because she had major inroads made into a scrumptious dinner for the four of us – a pot roast, but with all the trimmings. Sarah expressed her pleasure and wanted to help, but there wasn’t much to do.

Dad got us some wine, and we sat around in the kitchen-family room area talking about the Florida weather, our flight, and other topic-neutral material. Sarah had a cocktail napkin in her hands and was slowly turning it into confetti as she twisted, turned, and tore the paper in her hands. She was nervous. The moment of TRUTH was rapidly approaching.

I caught my father more than once staring at Sarah and taking in her charms. She hadn’t dressed provocatively, but she was always appealing in whatever she wore. She truly was one of the most beautiful women that I’d ever seen.

About seven-thirty, we sat down to eat, starting with our salads. The conversation stayed light. Eventually, Mom took us onto dangerous ground as far as Sarah was concerned. “In our video call, you said you were the head of finance and accounting for a company that builds boats?”

Sarah talked about Jaycor, some of their spec products and also the custom-made larger boats that were nearly ocean liners and that cost many tens of millions. I could see the enthusiasm she had for the job. She told about part of her work in arranging financing and loans on the larger craft. Sarah was also talking at a rapid rate of speed, betraying to all of us that she was nervous about something.

Mom then asked a logical next question, “Who were you with before that; I guess even before you moved to Sarasota? Why’d you move with no job prospect?” I forgot that we’d mentioned those facts in our video call, but no one followed up on them.

Sarah took a sip of her wine – then took a huge gulp, and swallowed. She looked at me for support and I nodded and smiled at her. She said, “I was an actress in adult videos and movies. I lived in L.A. and then Las Vegas, but I wanted to leave that behind and start in a longer-lasting career and something more ... socially-acceptable.” I could almost hear the ‘gulp’ she made after that statement. She looked around waiting for an explosion.

I think it took each of my parents a full sixty seconds to take in, evaluate, test, play back, and re-evaluate those sentences, retest, and then process what Sarah had said. My Dad did the follow-up question; “You mean porn?” His tone was pretty neutral. He cocked his head to one side, almost like a dog does when paying special attention to his master.

Sarah nodded and sat a little more erect and alert in her chair. This was her moment of truth. “Yep. Did it for over ten years. Paid for my college education and saved up a lot of money so that I could leave the industry with a healthy nest egg.”

She paused, and I could tell she decided to go for broke. “I also did some exotic dancing in a strip club, and was an escort; it was almost de rigour as a sex worker in the industry. One of my clients ran a hedge fund and helped me with budgeting and then investing early on. He had me buy into Bitcoin, Nvidia, and Apple and a few other stocks when they were dirt cheap and then had me sell out after they’d soared and leveled off. I do still have a diverse portfolio, however.”

Mom asked with real curiosity, “Exciting or a downer when you think back on all that?” The tone of her voice seemed to be on the edge of her own excitement. I did a double-take; she was happy at what Sarah had done. She smiled warmly at Sarah, so I knew this was going well. I wasn’t sure what Sarah thought.

Sarah thought for ten seconds, “Both. The sex and filming were exciting and so were the associated parties and real movie stars that I met. There is a rough edge where the actors in adult films do mix with actors in legitimate films. There were even a few cross-overs for some of the minor players.