A Young Swinger's Tale

Codes- FF, MF, first, group, oral, interracial, toys.

Intro- This story is fictional and meant for mature open minds. It contains graphic adult behavior. All characters are over age 18 at the time of their sexual activity and depicted explicit thoughts. Please do not read this story if you do not think you will enjoy it. If you do enjoy it, feedback is welcome.

This is connected to many of my previous works, but none are required reading unless you wish to spend more time in my fictional universe. If you need specific direction to connected stories, check my listed works on this website or drop me a line. Please take note that, like all my stories, this one takes place in an alternate urban fantasy universe. That should explain the alternate history details and fanfic cameos- Disney and Marvel own the characters in question. They are not onscreen characters in this story, so I do not consider it fanfic even if it takes place on one of Marvel's infinite Earths.

Ok, nuff said. Time for the story. :)

***

New York, NY. Winter 1996.

Hello Diary! Tess Winfield here again.

Great news! One of my longtime crushes finally culminated last night. I slept with Lisa, my high school best friend! It was great, as expected. Not the last time we'll hook up, we both agree. Now I'm sitting here the morning after, reflecting on the event and all that led up to it. Indulge me as audience, please.

We have discussed sex happening between us before, Lisa and me. You know about it too, Diary. But I'll remind you so you don't have to look back. I met her in my junior year of high school. My parents moved our family from New York to Houston because of a staffing shakeup at a sister hospital to the one that employs them. Not the first time they did such a thing. As their kid, I had to go along once they answered charity's call. The move we thought was temporary at first became a two year affair when we all decided we liked Houston and the staffing woes went on. My folks didn't move back to New York until after I graduated high school. I came here to attend Columbia, legacy student in the medical program.

Lisa's a classic curvy redhead fantasy girl. I'm a mousy little brunette, still worthy of appreciation but a different flavor than her. I've always been attracted to both guys and girls, her included. After my eighteenth birthday, I got serious about it. I'd dated before then, but sex was never on my mind. I was below the official age of majority, so it wasn't happening even if I was in a state with an age of consent lower than eighteen. My parents and other authorities made that clear. Some girls I knew lost their virginity younger, but not me. I went along with the demands to keep my folks' good favor. Then I turned eighteen in November 1994.

Finally, I allowed myself to think about my fantasies in depth and enjoy how my body reacted. It was so wonderful! As you know, I've written about it to you before.

Remember how I lost it? We came home to Manhattan for a week in November 1994, so I could enjoy the city as a legal adult on my school's fall break. My former grade school crush Shaun, all grown up and cute, asked me if he could be my tour guide when I emailed him I was coming back to the city. I said sure. We saw some couples kissing on top of the Empire State Building. He asked if he could kiss me too. I had never been kissed before, and I liked him, so I said yes. He was a great kisser. After a few more fun times at Coney Island and other tourist attractions the next day, I gave in further to his advances. He had some lasting hopes- I could respect that.

We got a hotel room alone, spent the night together. I told my parents what I was doing, said I didn't need their permission. They shrugged it off like all cool parents do. Shaun and I made out, exchanged handjobs, then banged missionary. Shaun was a bit of a fumbler, but he had potential. I spent two more nights with him trying out other positions before I went back to Houston. I started grade school a year late- parents call it academic redshirting. I had about a year and two thirds left as of my eighteenth birthday.

At my Houston high school, the cutest most eligible guy was Lou Stanton, our quarterback. Lisa and I were cheerleaders, naturally we were attracted to him. Lou and Lisa shared a neighborhood growing up fellow redshirts. He was already her first kiss, so I let them date with only mild envy. Lisa wasn't the only girl he dated- he was a roving womanizer who went through girls like Don Juan. Didn't always dump his previous dates before he started dating other people either. Some girls shamed him for that, others were okay with it. Lisa and I were in the latter group- mostly. We watched Lou love and leave lots of girls all through high school. Far as I know, it didn't progress to sex till our senior year.

The first month of that school year, he dated Morgan, our cheer captain, who was a serious bitch. He slept with her, then dumped her in Lisa's favor. Pissed Morgan off, that was her problem. Lisa and I were never her friends. We were on the same cheer squad, yeah, but the coaches picked us, not Morgan. I had prior experience coming in my junior year. Lisa was the biggest newbie on the squad, curious about cheerleading. Her skills in martial arts and school theater got her in. I had just moved to Houston, but Morgan and her posse were always after me because I was a Yankee. Guess they forgot we live in the 1990s, not the 1860s. At least Lisa was willing to be my friend! We bonded as the only anti-Morgan girls on the squad. She couldn't get rid of us, hated it, we forced her to deal. Lou and the team backed us, so did the coaches and most of the rest of the school.

Lisa and Lou broke up three months into our senior year, they were always off and on. She dated three other guys as the year continued. I asked her about dating Lou at one of our sleepovers. I was into him, but always scared of him a bit too. He never asked me out, always looked right past me for whatever reason. I asked Lisa how to get his attention, how he kissed. She showed me and then hooked us up. Lou was an awesome lover- pounded me hard way better than Shaun did and introduced me to oral sex. I enjoyed giving him blowjobs and letting him suck me off many times.

I let Lisa keep kissing me the rest of the year casually too- we were both bi-curious and close friends, why not explore a bit? We never got past making out while we were in high school, though. The idea that girls into other girls just smell each other and dive right in all the way is an erotic myth. At least it was for Lisa and me. I wasn't her first girl kiss- I think that was one of her uncle's biker friends- but she was mine. We did awkward fumbling like any hetero couple. Yeah, I was accepting of alternate sexuality- my parents were on the protest side of Stonewall and raised me with the same values- but turning on my polyamory interests took a bit of time. Natural shyness, waiting for eighteen, hormone management- you know how it works.

If Morgan hadn't caught Lisa and me kissing in the locker room after our Homecoming game triumph, things might have gone all the way between us sooner. We were enthused at the time, forgot we weren't public. You don't blame us, right?

Morgan, the bitch, saw her opportunity when she witnessed us kissing. She mocked us before everyone else, even tried to kick us off the cheer squad for violating school public affection policies. Our super cool principal, Dr. Cammie Funk, reminded Morgan our school was a tolerant environment and shut her down fast. Her crap still hounded Lisa and me, though, made things awkward for us. The worst part? We never got revenge. We decided to compromise with Morgan, hold back our consummating until college and shame her for forcing that on us the rest of the school year. Lisa and I agreed doing worse was too big a risk. Morgan had to deal with our needling, that was the only revenge we got.

Then of course we wound up going to different schools. Lisa had the grades for Columbia but not the cash. Her family had five kids and no legacy to get her a discount. We hated that, but didn't let it ruin our friendship while it lasted. We kept dating guys, Lou and others. We let the worthy ones know about our divergent interests, turned them on with it. I expanded my sexual practices with the guys, did anal and other things. Lou encouraged me as a direct partner, Lisa from the sidelines. We even had an orgy with Lou and two other lucky guys after our prom, though again we concentrated on the guys that night and never went further than making out with each other. I blame having too many other partners tiring us out.

Morgan hooked up with her date that night too, stopped giving us hell the following week. She finally gave up hating, I guess. I have too, even though sometimes I still want revenge on that bitch.

Lisa often tells me happy appropriate success overcoming fiendish plans is the best revenge. I have accomplished that as of last night, I suppose. And it feels great! Maybe she's right.

After I got to college, I wanted to lose my bisexual cherry fast. I knew where the queer-friendly bars in New York are and I visited them. Plenty of young women into virgins and hook-ups there, I scored within a couple weekends. Stonewall was crowded that night- I went to a similar place in Harlem. Hooked up with a full-figured black girl named Aisha, had a great time. You can look back at the entry if you like. Or if you want reminding here and now...

I hit on her first that night. I was high on crazy dreams. I had been with black guys before, but hadn't yet been with a full-figured person or a girl. Aisha was cute, I was into her after I watched her walking around the club a bit. I bought her a drink- no alcohol, we were both nineteen and thus underage- but the tactic still worked. She quickly agreed to hook up with me that night after I told her my history. We went to her apartment, spent the rest of the night together. The first thing she did to me was finger me- that's always easiest for me to get into with another person. It's a natural progression from making out.

Next I had her go down on me. Lou and other guys had done that to me before, but a girl never had. I've always heard women do pussy-licking better than guys. I only give them the edge by a slight margin. Guys can be fun too. I don't think I'll ever drop them entirely.

Aisha really made me gush when she licked me. Tickled my clit and sucked my cunt in many great ways. I was very turned on by it. Things got even better when she taught me to return the favor. The memories still shake my insides and get me hot.

Our next few nights together, we tried out her toy collection. That was also loads of fun. We used vibrators, hand dildos, and strap-ons. I adored it all and soon built up my own collection with Aisha's help.

I still date her off and on. We've had swap parties and group sex with some of her other girlfriends and boyfriends too. I've kept it casual, haven't fallen for anyone yet. I've texted and emailed Lisa about it throughout, had fun making her jealous and turning her on. She wanted to hook up with girls at her college in Austin all her first two summer semesters, but had issues with chickening out. Or she went for guys because she found them easier to seduce. I reminded her what she always told me- she had to expand her mind and open herself or she was never going to get out of her shell. Lisa reminded me it's a two way street- I was lucky to find more willing partners than she was. She didn't always get lucky.

We made plans for her to come visit me this month. If Lisa hadn't lost her girl cherry by then, I would take it. Aisha had other plans for the holidays, or she'd help. Lisa agreed with my proposal.

Then she had to go and accept her roommate seducing her back in October! So disappointing! Oh well.

She and her roommate scored with three other girls in their dorm a week later and now have regular orgy nights two or three times a month, just like me. One on one hookups with guys too, and the occasional casual threesome or moresome. Oh well, I may not have gotten her girl cherry, but we still kept our plans. Phew!

She flew into town three days ago. I picked her up at JFK, showed her around the city like Shaun did for me way back when. I wanted to be with her our first night together in my apartment, but Lisa wanted to take things slow. She always does that with relationships she wants to last. I told her we already had enough history, then went along with her after she gave me enough assurances. We renewed our casual making out, too, and this time, the promises were heavier on our minds. There was also no Morgan and less awkwardness to get in the way.

We bonded further reminiscing about our past and chuckling over the antics of the local anti-vigilante lobbyists. They have never succeeded in New York since we got local crimefighters like Spider-Man and the Gargoyles everyone not in the know thinks are an urban legend. The police can't do everything, enough of the public know that, and good political players back the heroes up. Jameson, Osborne, Guiliani, and their shame crowd can never succeed, not in this world. They can try to win elections, but it never happens. Or on the rare occasions they do win, they get kicked out in due time. Or shut down and never accomplish much other than hyping their crap with laws that don't last or only drive us libertines underground. Heh.

On our third night together, last night, Lisa finally gave in to my advances. We had dinner together in Soho, held hands walking through Central Park, kissed outside the Natural History Museum. It was understood she wouldn't be spending last night on my couch. We caught a cab from the park back to my place, resumed our making out soon after we walked back in, and it happened.

The first time was on my living room couch, rabid dry humping with wandering hands we finally let move to the right spots. I pulled her shirt up, caressed her abs and back muscles, areas I've always admired on her. Things progressed quickly. I moved her shirt up further so I could get at her breasts. She opened my pants and started fingering me quick to calm me down. Her groin was rubbing my knee the whole time, her pants on but wet. Our lips were exchanging contact too. I came only seconds before she did. We were both sucking on each other's tongues, then pulling away from each other as we found release.

Lisa and I laughed in the aftermath, separated briefly to get naked, then moved things to my bedroom. We got on my bed and enjoyed each other's company the next three hours. We made up for lost time in many ways. Mutual fingering first, we both had two fingers in each other. We followed that with tribbing, then sixty-nining. We broke off for a midnight snack and bathroom visits after that, then resumed. We got out two of my Companion vibrators- she didn't want to bring hers on the plane- and used them on each other. Then we used one of my strap-ons. She wore it and brought me off. I was too tired to keep going after that, or I would have returned the favor on her. Maybe tonight I will.

We slept beside each other in my bed, then did some shower play this morning. That was fun too. Cleaning each other, moving quickly to a vaginal fingering exchange and tribbing against the wall once we were turned on, then cleaning up again. Now I'm relaxing while I wait for her to finish getting ready for our trip out today. The Modern Art Musuem, Guggenheim, and a few other places are on our list. Maybe we'll swing by the 23rd Precinct Clock Tower again and look for swooping Gargoyles once the sun goes down. If kissing isn't on our minds. I think it will be, though. Just thinking about being with her... it gets me so excited. And she's only in town four more days!

But we'll still be friends for life, I know that. The parting will only be temporary. Surely, in time, we'll see each other again.

Lisa's walking into the room behind me now, shaking her head as she watches me type. She's ready to go out now, she tells me. Am I ready? she asks.

I nod yes at her, type a few last words, then shut my laptop and stand. Bye, Diary. Talk to you again soon. Tess Winfield out!

***

End.