Chapter 1: Discovery

I didn’t know they were sisters when I started dating them.

I was thirty-two, and the girls were a couple of years younger, but with different last names and with birthdays about six months apart. I met Fran at a graduation party of a friend finishing his MBA, and Sheila at a Sunday afternoon birthday party in Marblehead. Stepsisters as I found out the hard way. They’d been together for so long they didn’t bother to use the ‘step’ word when referring to their relationship.

Sheila was a tall, lanky blond with a passionate streak I just knew I wanted to tap into someday soon. Making out with her made you feel like you were flirting with a volcano about to blow. We’d start slow, just a kiss or two, and then suddenly there she was in my lap with her tongue down my throat and her hands doing interesting things to both our bodies.

Fran was a short brunette with a determination to do everything she did perfectly, including making her boyfriend (me?) happy. When we started making out, I felt she was searching and learning at the same time. Searching for the places and techniques that would turn us both on to the perfection she desired in our relationship, and learning and memorizing these places and techniques so she could invoke them later. She got me thinking the same way.

I had been open with the two of them about not being exclusive. After a few get to know you dates, I had standing dates with Sheila for Tuesday and Friday nights, and with Fran for Wednesday and Saturday nights. Sundays I seemed to alternate between the two of them. While I didn’t talk about one with the other, I made it obvious to each of them that I’d been on other dates with ‘someone else’. For instance, Sheila and I saw the movie Gravity one night; the next night Fran wanted to see it too, however, I explained that I’d just seen it the night before with another ‘friend’. I guess I wanted to emphasize the fact that I dated others; she didn’t pursue the matter, and we ended up seeing another movie. Managing expectations was important to me.

I am a romantic at heart. With both women we went on a healthy diet of candlelight dinners, flowers, carriage rides, dancing – sometimes in my small but exceptionally neat and polished Cambridge apartment, and of course stimulating discussions when we were in public, for instance walking arm in arm along Boylston Street in Boston on a hot summer evening. We were learning about one another, and on that front I was very open about myself. Thinking back on it, I was looking for long-term relationship and a marriage partner.

My relationship with Sheila ran parallel with the one I had with Fran on a nearly day-by-day basis. Week One, after meeting at a party, I called and we agreed to do coffee a few days later, had several get to know you dates over coffee and lunch near our work, and agreed to something more significant a week or so later.

We enjoyed some simple kisses together, but nothing to write home about other than it was clear we were comfortable with each other.

Week Two, we advanced to making out with each other and I could tell we were both feeling great resonance with each other. We found we shared many common interests, yet had a few that were independent of each other. By the end of the week, we’d smothered first base with a huge load of French kisses and nearly constant physical contact, although I was ready to dispense with some of our clothing.

Week Three, we got to second base with each other. For those of you unfamiliar with the baseball analogy in dating, that meant that we started to pet in a way that stimulated some of the sexual parts of our bodies, more specifically Sheila’s (and the next night, Fran’s) breasts and my crotch, although everything was perpetrated outside of our clothing. Damn.

Week Four, we got under each other’s clothing and even bared some of our usually hidden skin to each other. I peeled Sheila’s top up around her neck so I could lick and suck on her breasts, and she opened my fly so she could fondle and arouse my cock to her heart’s content. I ended with blue balls that I had to contend with when I got home from our date.

Week Five, Sheila surprised the hell out of me when she went down on me, giving me a somewhat amateurish blowjob, but I was in no position to complain. I acted the gentleman and warned her of my impending climax, a move that allowed her a graceful retreat, as she finished the act with a masterful handjob. This was all accomplished on the sofa in my small apartment. When I offered to return the favor, Sheila made out with me for a bit and said, “Maybe next week. Let’s not rush things.” I accepted this slow rate of progress as the price to pay for being with this pretty young woman who was definitely long-term material.

I’d fallen in love with Fran and Sheila, but not told either one. I think they felt the same about me. Most guys would decide on one or the other, but I not only couldn’t, I didn’t want to because to pick one would mean I had to do without the other. Fran or Sheila. Sheila or Fran. When I was with one, I worried about the other. I wanted to be inclusive with both of them.

Week Six, I seduced Sheila (and Fran) into allowing me to perform oral sex on them. We’d made it to third base. I felt myself reasonably skilled in the techniques of cunnilingus, so once I had her permission I truly made love to her pussy delivering multiple orgasms one after another. We were nude, and I got another blowjob, this time to completion. My date with Fran went along in parallel.

Sheila and I had avoided using the ‘L’ word with each other up until that time. In the heat of her fifth orgasm of the night, Sheila said, “Oh, God, Steve, I love what you’re doing to me. I’m falling in love with you.” Amazingly, Fran said nearly the same words in the same situation the following night.

The fact is I was falling hard for Sheila, and simultaneously I was falling for Fran. I started to feel conflicted, knowing that soon I would have to make up my mind about the two women, picking one to focus upon and to date exclusively. Even at this stage, however, neither Sheila nor Fran suggested exclusivity.

As soon as that thinking permeated my brain, another side of me would argue that I was too young, or indecisive, or afraid to make a mistake, or something, to pick one of the two at this stage. I kept hearing one of the voices on my shoulder telling me to keep insisting on non-exclusivity, and keep dating the two of them, and for that matter any other woman that might appeal to me. Any downside to that philosophy hadn’t occurred to me.

That devil on my shoulder would convince me that at my age, I wasn’t ready to settle down or make a lifetime commitment with anyone, and that I had plenty of time to eventually find a life partner, start a family, and do ‘adult’ things. Both Sheila and Fran qualified as ‘keepers’ in my long-term plan, and one of them indeed might end up the Mrs. if things progressed nicely.

The gods are fickle and laugh at us mortals. I had a comfortable bachelor life, dated two of the most gorgeous women on the east coast, had an excellent job that paid well and that I found exciting, and had a larger circle of friends I enjoyed. Hubris is a word from the Greek tragedies implying excessive pride or defiance of the gods leading to inescapable downfall and humiliation.

Things reached a turning point on a Saturday night.

I reluctantly gave up an entire evening of eating Fran’s pussy (and to hopefully make it to home plate) to accept her invitation to drive out to the suburbs and meet her family – her mother, father, and two sisters. We hadn’t talked much about families up until that point except in broad generalities. Our focus had been on each other and talking about our schooling, friends, and jobs, or other intellectual or newsworthy topics. As odd as it would turn out to be, I had made a similar dinner commitment with Sheila for the following Tuesday evening.

I picked up Fran in front of her apartment at six that Saturday evening and we happily started the forty-minute drive out of Boston to the town of Dillon to her family’s home. Some niggling point bothered me as I drove, and it had something to do with Dillon. I had met someone else recently that was from there as well but in the heat of the evening, the information wasn’t coming to mind. I put the thought aside to concentrate on Fran’s description of her father and mother, and how I might get on their good side.

My thoughts were all over the place as I drove since Fran was also nibbling on my right ear and kissing me passionately at every ‘safe’ opportunity along the route. We enjoyed a lot of tongue play in those moments during the drive, plus she was running her fingernails up and down my thigh leaving me with a hard-on that could cut steel. As we neared her home, I stopped her since I knew I didn’t want to ‘show’ when I met her parents. How would I explain that?

I parked in front of the large suburban home that announced a well-to-do upper-middle class family. Fran and I stood by my car and made out for a couple of minutes, before she insisted that we go on inside. She laughed but allowed me to ‘deflate’ until I was presentable. She promised an ‘interesting night’ if we could finish dinner and get away early to return to my apartment. I liked the sound of this – home plate with her was in sight. Fran even promised to spend the entire night with me, something I’d asked her (and Sheila) to do without prior success.

We bounded up the front steps together, and went in through the front door. Just inside the door, Fran yelled, “Hey everyone, we’re here. Hellllllloooooo.”

From what was obviously the kitchen, Fran’s mother, a beautiful look-alike older blonde woman arrived with her hand outstretched. “Steve, it’s so nice to meet you, and please call me Jean. This is my husband Dave.” Dave smiled as he joined us to shake hands. He was a tall, muscular man with salt and pepper hair. Fran’s younger sister Allison joined the welcoming committee, and she also gave me a polite hug. We were shaking hands and nodding at each other...

And then...

... my blood ran cold, and I froze in position, praying that a hole in the ground would open and swallow me in one fast death-dealing gulp.

Sheila stood in the kitchen doorway also frozen in mid-stride. Our eyes were locked on one another briefly, and then my head got light and my leg muscles gave out, and I sank to my knees in the home’s foyer.

A hundred tiny pieces of information suddenly all clicked into place: parents’ names and ages – the same; the composition of the family – the same; living in Dillon; a sister named Allison; and many more.

How could I have missed the patterns – the similarities – the identical descriptions of things? I briefly thought about how I compartmentalized each of my dates, so much that I hadn’t compared what I heard from one of them with what the other told me. I mentally kicked myself around the block.

Fran fussed over me, feeling my brow with her cool hand and rubbing my shoulders. I think she thought that I got faint because of meeting her parents.

Jean raced away to get me a glass of water and cool paper towel. I waved them all away, as I struggled to stand again. Dave helped me up. Allison held my other arm to be sure I didn’t fall her way.

I did a quick reconnaissance of the faces. Fran looked remarkably like her mother. Sheila looked like a clone of her father. Ally looked like a mix.

My knees wobbled again. I realized I was dead meat. I’d blown it with two girlfriends I really, really liked and had hoped to get more serious with. I felt tears well up in my eyes over my sudden loss. I had trouble swallowing.

Fran and Dave helped me sit on the stairs in the entry hall. I put my head in my hands and tried to think of what I could say or do to rectify this really, really, really awkward situation. I was shaking my head hoping I’d awaken from this nightmare.

As I looked up, Sheila slowly came forward until she stood next to her sister. Sheila pointed at me and in an angry tone asked Fran, “THIS is the guy you were telling me about?”

Still not attuned to the situation, Fran eagerly replied, “Yes, this is Steve.” She still sounded concerned for me, but I guessed that would change any second to one of rage. I checked the area for obvious weapons. At this point, I marveled that only thirty seconds had passed, yet I knew I had to endure the pain that I felt inside before I could safely retreat back to my apartment in Cambridge and take a lifelong pledge of chastity and monkhood. I’d enter a monastery.

Sheila turned to me and said in an angry and sarcastic tone, “Nice to meet you, Steve!” In that instant, I felt particularly glad she hadn’t come from the kitchen carrying a long serving knife. I glanced at her hands to be sure.

Fran only now picked up on the dynamic between Sheila and me. “Errr, do you two know each other?”

Before I could say anything, Sheila said, “Oh, yes. Steve and I have been dating for the past two months. He’s the one I’ve been telling you about.”

Fran’s mouth dropped open at the news that I had also been dating her sister. She whirled around to look at me instead of her sister.

The girl’s parents looked at their two daughters and me with questioning and puzzled looks. They hadn’t yet caught on to what had been happening.

My brain had crashed, just like my laptop did all the time. I tried several times to push the restart keys to no avail, but finally I started to get a solid reboot and some of my brain function started to return. Core memory and functionality were serious damaged.

First, I realized I was most likely single again. The two girls I’d been dating and falling in love with would hate me from this moment on, and remember what a heartless asshole I’d been, particularly to show up for dinner with one when the other was home. I thought how their opinions would influence a wider circle of friends and I would be banned from further dating in that circle for the rest of my life.

Further thoughts dealt with my avowed stance of non-exclusivity, not a secret from either Fran or Sheila. Another thought dealt with sex, particularly the fact that I hadn’t had a consummating evening with either of the sisters; a point I thought might bode well for one or both of them eventually forgetting this humiliating situation. Last in my pea-sized brain, I had just deduced their relationship.

I mumbled in disbelief, “You two are sisters? Step sisters?” Not the most subtle or brilliant of statements given the circumstances.

Fran said in a voice now tinged with anger, “Yes. Is what Sheila said true? Have you been dating her, too?”

I said with slightly more authority, “Yes, I have been dating the two of you. I have been honest with you about not being exclusive ... even encouraging you to see others if that seemed to be something you wanted. I just didn’t know...”

Sheila interrupted and turned to her parents, “THIS is the guy I was going to bring here for dinner on Tuesday night, except Frannie beat me to it.” She stomped her foot on the bare wood floor in obvious anger and frustration, a move that caught everyone’s attention, and then she gave a sudden sob and fled into the kitchen.