Dorothy was my best friend in college. When we first met, she was, by her own definition, “straight”. But her definition of straight changed like the wind. Dorothy was the first woman I had sex with, and vice versa. She framed this event as an act of charity – to help me determine whether I enjoyed having sex with women – as if she somehow represented all women on the planet. After having sex with me, she decided that she also had to sleep with her best friend from high school, who would be crushed if she ever found out that Dorothy had slept with any woman other than her. Thus one charitable act led to another, and soon Dorothy was shepherding me into sexual configurations of various numbers and genders. Since I was the shy one, I was happy to rely on her to organize our sexual forays. Until she finally came out as bisexual, she had a way of organizing group sex, then fleeing the scene, racked with guilt. As I later discovered, Dorothy fantasized about having sex with virtually everyone she knew, and my burgeoning bisexuality provided an opportunity for her to test-drive some encounters that would otherwise have been difficult to rationalize, given that she still called herself “straight”.
My first threesome was orchestrated by Dorothy and a guy she was fucking named Matt, who happened to be my ex-boyfriend’s roommate. What I remember most about the experience was Matt’s effort to make sure everyone felt included by mentioning both our names as he came: “Oh, Dorothy . . . oh, Lisa.” As I fell asleep that night, I couldn’t help feeling as if I’d just had my first bisexual experience, even though I’d already identified as bisexual for a year and had sex with both men and women individually. Nonetheless, if I had sex with a man at 7 p.m., and a woman at 8, who’s to say I didn’t go through a heterosexual phase at 7 and find my true lesbian identity an hour later? After my first ménage à trois, I felt as if I’d jumped through the final hoop of true bisexual identity.
We finally cornered Dorothy into coming out as bisexual. It was a bit like gang warfare, and it happened during a surprise party that I organized for her 19th birthday.
Several months earlier Dorothy had confided her core childhood masturbation fantasy in the wee hours of the morning, when our inhibitions were down. Since the age of seven, she had fantasized about crawling through a paddy wagon of authority figures, consisting of her grammar school teachers, camp counsellors and babysitters. Eventually, she came to the last link in the chain – the school principal, who would spank her hardest of all. That was the part of the fantasy that made her come.
I admired Dorothy’s sexual precocity. But I also realized that she was telling her childhood fantasy from the perspective of her present 18-year-old self. She was thus embellishing this particular fantasy with a knowledge of sexuality that she eouldn’t possibly have had as a seven-year-old. I concluded that the paddy wagon was a present fantasy, which Dorothy was unconsciously projecting onto her childhood – probably because she felt less guilty telling it in the past tense.
In any case, spanking was Dorothy’s biggest turn-on. She wanted to be punished. Unfortunately, she had a hard time asking her sex partners to whack her on the butt. After all, we were only 18, and most of us hadn’t evolved much in the way of sexual communication skills. Organizing group sex, then fleeing the scene, was a circuitous and ultimately unsatisfying route to getting what she wanted. I decided to make it easier for her by giving her a surprise paddy wagon for her birthday.
I got stuck on the question of which authority figures to invite. We were in college at the time, but professors were out of the question. Graduate students, on the other hand, were predatory beasts, lying in wait to seduce young undergrads, hoping to gain some semblance of respect, which the university denied them.
So I invited Megan, my neurotic girlfriend, who just last week had been studying for her PhD exams while Dorothy, Matt, and I fucked in my bedroom several blocks away. Megan would have been happier if I had forewarned her of the threesome, or even asked her permission. But at the time I was unpractised in the ways of polyamory, which is a nice way of saying I was cheating. I also invited Megan’s best friend, Michael, who was Dorothy’s former teaching assistant. Megan and Michael had slept together, I knew, but Michael was primarily attracted to men. His boyfriend, Daniel, was an undergraduate and a mutual friend of Dorothy’s and mine. (Dorothy had engineered a threesome with Daniel and Michael the summer before.) So I invited Daniel too. I also invited Chelsea, my quiet bisexual roommate, and her loud boyfriend Jeff, a graduate student in the French Department, who wanted to be bisexual for political reasons. Martin was Jeff’s best friend and a local drunk. He was capable of brilliant conversation and occasionally fucked my girlfriend, but was otherwise generally useless. Jeff and Martin were 30 and 32 years old, which seemed ancient to me at 18, so I thought they’d make good authority figures for the paddy wagon. Finally I invited my ex-boyfriend Tom, who could be a stick in the mud. Dorothy didn’t really like him, but since I was inviting Matt, and Tom was Matt’s roommate, I had to invite Tom too.
I told all the guests about the paddy wagon, although I didn’t tell them it was Dorothy’s masturbation fantasy. I just told them she’d like it a lot. I was secretly hoping the event would turn into an orgy – although I didn’t tell everyone that, either. To decrease the likelihood that people would stomp off in disgust, I tried to invite bisexuals, or at least people who were willing to have sex with both men and women.
The night of the surprise party, I invited Dorothy and Matt to come over at around 8, just to hang out and celebrate her birthday, perhaps with another threesome. The guests arrived an hour early. They were supposed to stay in the living room, so Dorothy wouldn’t see them when she first walked in. When the doorbell rang, they quickly got into paddy wagon formation – standing in line with their legs spread so that Dorothy could crawl through. I opened the door for Dorothy and Matt. We chatted in the kitchen for a few minutes. Then I quickly led them into the living room, so that the guests wouldn’t get leg cramps from holding their paddy wagon positions too long.
“Surprise!” they yelled, as I opened the door.
Dorothy’s jaw dropped. “O, my God, what are you all doing?”
“You have to crawl through our legs!” shouted Jeff, who was at the front of the line.
It took a few seconds for Dorothy to get it. Then she blushed deep red and ran out of the room.
“Hey, wait!” Matt and I grabbed her arms and dragged her back in, virtually kicking and screaming.
“Come on! Crawl through!” the guests demanded. “We can’t stand here all day, you know.” They were starting to fidget.
“No,” Dorothy insisted. “Not unless everyone else does.”
“You first. It’s your birthday.”
Dorothy blushed deeper, but finally got on her hands and knees in front of the line. She hesitated. Matt and I stood right behind her in case she tried to bolt.
She looked back at us. “I can’t believe you’re making me do this,” she said.
Dorothy started to crawl. As soon as she was halfway through Jeff’s legs, he administered a loud whack on the butt, then drummed on her ass with both hands.
“Ouch!” she wailed. “Ow, ow, ow.” I’d positioned Jeff at the front of the line, because I knew he would spank hard and bold – demonstrating to everyone else how it was supposed to be done. Chelsea came after Jeff. Her spanking was tentative, but Megan’s was hard and stingy – she was a mean hardass, when it came right down to it.
Michael was next in line. To everyone’s surprise and delight, he grabbed the elastic waistband of Dorothy’s sweat-pants and pulled them down, exposing her bare butt.
“Oooooh,” we cooed.
“Hold on. That’s not fair,” Dorothy protested. But Michael and Matt were already caressing her naked ass.
“You don’t want us to stop now, do you?” Michael asked, as he spanked her ass with one hand, stroking it with the other.
Dorothy didn’t say anything. But she was sighing and wiggling her butt, clearly enjoying it. I could see Matt’s cock swelling under the zipper of his jeans. He knelt down beside her, and they kissed. Dorothy was still on all fours between Michael’s legs. Michael was still spanking her, and there were three people left in the paddy wagon line: Michael’s boyfriend, Daniel; my ex-boyfriend Tom; and Martin, the drunk.
Then mayhem broke loose. Daniel spanked Michael, Megan spanked me, as about five hands stroked and spanked Dorothy’s butt. Michael slipped his fingers between Dorothy’s wet pussy lips. Dorothy was squirming. Matt unzipped his pants.
“Hold on,” Dorothy interrupted, standing up. “I’m not fucking all of you!” Michael, Matt and I exchanged glances.
“Oh, yes, you are!” we said in unison.
Matt and I grabbed her and held her still on all fours.
Dorothy screamed, but there was no one to save her. My next-door neighbour was deaf, and the people upstairs were insane. They were building a bomb shelter on the second floor. Screams were nothing out of the ordinary.
Michael took off his pants. Daniel stood behind him, grinding his crotch against Michael’s butt. “Why don’t you fuck her while I fuck you?”
“Hold on there. Ladies first.” Megan sat down beside Michael, wearing a strap-on, which she must have grabbed from my bedroom when she saw where all this was going. Meanwhile, Dorothy had stopped screaming. Matt put several fingers inside her, as I caressed her butt.
“You OK?” I asked.
“I guess so. For the moment.” Still on her hands and knees, she wiggled her ass in the air.
“She’s really wet,” said Matt. I stroked her clit. She was dripping. I moved my fingers back and forth, then in circles. She moaned and squirmed.
Megan was wearing a huge red dildo. She covered it in lube and pressed the tip against Dorothy’s cunt. When it was all the way in, Megan waited as Dorothy adjusted to the huge dildo.
Meanwhile Michael and Daniel had positioned themselves in front of Dorothy. Daniel stroked his cock right in front of Dorothy’s face. When he was really hard, he put a condom and lube on his cock. Michael got down on all fours, and Dan entered him from behind. Dorothy, Megan, and I all got excited, because we love watching gay porn; it was an even bigger turn-on live.
Megan pumped the big red dildo in and out of Dorothy’s cunt.
“Harder!” Dorothy demanded. The live gay porn had apparently transformed her from a quasi-resistant gangbang victim into an insatiable slut. As Megan thrust harder, Daniel did too, and for the next fifteen minutes, the loudest sounds in the room were those of pelvises slapping against butts. Matt and I stood by, administering random whacks to Dorothy’s ass. Chelsea, Jeff, Martin, and Tom had retreated to the sidelines and were providing a running pseudo-intellectual commentary, which I could barely hear over everyone’s groans.
Just as I noticed Matt had a condom on his cock, he threw me down on my back. I’d gotten so absorbed in spanking Dorothy that I hadn’t even realized how wet I was. Dorothy looked up as Matt entered me, and I recognized that furtive gleam in her eyes. I dragged myself closer to her, as Matt lay on top of me thrusting. Dorothy leaned over and licked my nipples. At that point, my ex-boyfriend Tom stomped off, slamming the door loudly. I didn’t know how he and Matt were going to live together after this, but at that moment, I didn’t care, and I don’t think anyone else did either. Meanwhile, Chelsea, Jeff, and Martin the drunk retreated to my bedroom to have comparatively boring sex with each other.
After an hour of hardcore fucking and multiple orgasms, we collapsed, exhausted. As we were lying around in a sweaty, pulsating heap, Michael asked, “So Dorothy, does this mean you’re finally a card-carrying bisexual?”
“I guess I’m not in Kansas any more,” she sighed. A big satiated grin spread across her face.