The Conventioneer Ch. 04

As Gwendolyn and Abby get to know each other, Gwendolyn shares a shocking story of her coming of age.

Readers: Thanks for taking the time to read my stories. I hope you will take a moment to vote and comment (good or bad). Doing so allows me to better understand if the themes I'm addressing are of interest.

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I was about to tell her a story I'd never shared with anyone. I stood and took her by the hand. "I need a bit more fortification." Abby didn't pull away as we walked to a bar near the shooting gallery. I ordered us each a shot of tequila and after wincing our way through, I said, "I attended community college in Palo Alto and met a girl in PE. Her name was Cassy. We were assigned a shower stall together and until that point, I'd never been so close to another naked person. It was uncomfortable for me, but Cassy was totally at-ease. I thought her confidence came from her age."

"How old was she?"

"Twenty-one."

"And you were?"

"I turned nineteen a few days before classes started. Even though we were relatively close in age, when it came to her body, she was confident beyond her years. At the time, I was incredibly self-conscious of mine and to make matters worse, I was being bullied by some girls in the locker room. They made fun of my breasts and pubic hair, which was really bushy at the time. They...threatened me."

"They were going to physically hurt you?"

"They said they'd hold me down on the floor and spread my legs while they took turns...fisting me." I turned away; it was a troubling memory.

Abby looked horrified. "That's awful, Gwendolyn."

"I was made to undress and jump up and down so everyone could see my breasts bounce. They called me bouncy tits. I had to...perform...everyday before class." All these years later, I still struggled to hold back tears.

"I'm so sorry. I can't imagine the humiliation you felt."

"Thanks." Composing my thoughts, I said, "But Cassy wasn't like me. Her hair was white-blond and her eyes were piercing blue sapphires. She was petite, almost elvish in stature, and very small up-top."

Abby looked down at her diminutive hillocks, slid her hands over them and said, "Like me?"

"Cassy was smaller," I said. "And you have nothing to worry about in that department. They're beautiful."

"Thanks," she said, tucking some hair behind an ear and smiling radiantly.

"Cassy was basically flat-chested, but she had very puffy areolas and pointy nipples. Her breasts were like ice-cream sugar cones, and I thought they were incredibly cute. She understood my plight, even if we were nothing alike physically. We were both different from everyone else and that's what brought us together."

"When did you know you liked her?"

"I'm getting there, just hold your horses."

She shot me a raspberry.

"As we became comfortable being nude together, we would sometimes help each other in the shower; I might wash her hair, or she would shave my legs." I explained how Cassy finally convinced me to prune the overgrown thatch of mahogany hair between my legs and actually did it for me the first time.

"It was your choice, wasn't it, Gwendolyn? She didn't force you, did she?"

"No, no. It was nothing like that. I wanted Cassy to shave me. But I was nervous my mother would find out. I'll explain how it was growing up in my house in a minute." I was suddenly aggravated that I was telling the whole story out of order.

"It's fine. I think I'm following you, honey." Abby patted my hand and I pushed on.

"It took a lot of convincing for me to finally agree but when Cassy finished, I loved it. The giant bush that made my panties and bathing suits look weird was gone. All that remained was a thin rectangle."

"When I was in grad school," Abby said, "a girlfriend did that to me once a week; although she preferred me completely shaved." Abby smiled. "It led to more than a few missed classes."

"For me, it really helped build some self-confidence. There was nothing I could do about my chest, but my special place finally appeared normal; I looked like other girls in the locker room. I felt...contemporary. Anyway, I started spending time at Cassy's house and became very close with her family. They had moved to California from Sweden because Liam, her father, was on temporary assignment to run a museum in San Francisco. She had an older sister, Louise, and a twin brother, Erick. Her uncle, Lars, was also very close to the family, as was Gustov, her mother's cousin. Looking back, though, it was Cassy's mother, Anne, who was probably the most influential person when it came to my burgeoning sexuality. But they all...enlightened me...to things I never thought possible."

I ordered two more shots and went on to tell Abby about the unique bond the Vatspalt family shared and how they made me understand the limitless emotional and sexual pleasure that can be experienced when you're willing to open your mind and accept new ideas and attitudes from both genders.

I also told her about being raised an only child by strict, religious parents, of being the daughter of a pastor. "The home schooling I received limited my contact with people my age and from understanding the larger world around me. I was taught that touching myself down there, much less shaving my special place, was dirty and would lead to promiscuity."

"God, that's practically Victorian."

I nodded. "But it was what I knew. So when I met Cassy's family it was quite a revelation. To me, the Vatspalts represented the opposite of everything I understood at the time. They were sophisticated and worldly and yet they always listened to my point of view and encouraged healthy debate. This made an impact on me because in my house, I was taught to obey; it was not my place to question."

"Reminds me of my childhood," Abby said. " My parents were very conservative, too, and it was Kansas." As if that explained everything.

"It wasn't until much later that I realized my submissive upbringing also played a big part in my relationship with the Vatspalts." I waved my hand. "But I'm getting ahead of myself."

"We have all afternoon."

"Because of Liam's profession, there was art everywhere around their home and much of it was highly erotic. There were statues and pictures of people fucking, of women sucking cock, of men going down on women, threesomes, foursomes, gay, lesbian, straight, anal, bondage, toys, sex slaves...basicially anything you could imagine was depicted somewhere in their house. The naked human form was everywhere and the Vatspalts celebrated it. To the contrary, bcause of my upbringing, along with my over-developed breasts, I covered myself up as much as possible."

"That's too bad," Abby said. "You have a beautiful figure."

"Because of the teasing I'd endured, it was just better to keep everything under wraps. But Cassy displayed her body. She never wore a bra and claimed she didn't own one. But that wasn't a big deal. You know how it is in college; bras are optional at best and she was small enough that she didn't really need any support."

"I rarely wore one in college," Abby admitted.

"I'm jealous. It wasn't until I had some work done after my second kid was born that I felt comfortable going braless."

"Yes but I did it because of girls like you, who had amazing breasts. It was the only way I could get anyone - guys or girls - to pay attention to me."

Somehow I doubted that, but I pushed on. "Cassy also never wore panties and she dressed in clothes that highlighted this fact. Tights and yoga pants...conformed...to the contours of her special place. When she wore a skirt, it was short and she wasn't concerned about sitting with her knees open. But it was never overtly obvious, which made her actions more arousing. Basically, she enjoyed exhibiting herself."

"Jeeze, this girl was brazen."

"At first, I thought so, too. But she was honest about it and pointed out that half the world had a snippa and pattar, which is Swedish for pussy and boobs. Her point of view was, 'who cares?' I couldn't argue with that and I found her confidence inspiring. After a couple weeks, I didn't really think much about it until I visited their house for the first time and realized they were all completely uninhibited about the human body."

"I bet that was uncomfortable."

"It was. I tried not to stare or be obvious, but I couldn't help myself. They were beautiful people physically and wore clothing that left nothing to the imagination. I wasn't really surprised to see Anne and Louise dressed like Cassy. But Liam and Erik were often shirtless and didn't bother with underwear. They wore snug-fitting lounge pants or shorts that were sheer enough to see their cocks through the thin material. I couldn't help but gawk at them. At least that's how it was in the beginning."

"I don't blame you," Abby said. "I've always liked the look of a man's cock, even when it's soft."

I giggled. "Me, too! And their cocks were...impressive. But after being around them a few months, I stopped noticing their bodies and realized their lifestyle was so open and honest that I found myself wanting to be like them. One day, I was at the mall with Cassy and her mom when Anne offered to buy me some new clothes. When we left the store, I was excited to own something that wasn't so conservative. It wasn't sexy; just a pair of skinny jeans and a snug-fitting blouse. But for me, it was a big moment."

"You were starting to come out of your shell."

"Since the Vatspalt's didn't wear much around their home, they kept it warm. So wearing less clothing was more comfortable when I spent time there. I didn't dress any differently around my house or in public, but in the Vatspalt's home, my bulky sweaters eventually gave way to form-fitting tee shirts and tank tops. The slim-cut jeans were later ditched for leggings and tights or short-shorts. I started wearing skirts and sun dresses, although I wasn't brave enough to go around without underwear. They had a pool and the modest one-piece bathing suits I wore at first were left at my house in favor of wearing the bikinis Anne bought for me."

Abby looked proud. "I can actually see the confidence now, as you're telling me about it. You're kind of glowing."

I smiled. I could feel it, too. "They really did bring out a side of myself I didn't think existed. But it wasn't until the first time I spent the night at their home that I really started to embrace their approach to sexuality. Cassy and I had gotten ready for bed and when we came out of the bathroom, Anne and Liam were waiting for us. They sent Cassy downstairs and took me to their bedroom. I was nervous they were going to do something with me; but was also excited."

"Oh, man." Abby absently ran a hand up her bare thigh.

"I was actually a little disappointed when they showed me a painting by Edvard Munch. It depicted a young nude woman who was self-conscious of her appearance. We talked for a long time about my body, and why I shouldn't be ashamed of it. I cried a lot when I told them what I'd been through. They hugged me and said I was special."

"It sounds like they really cared about you."

"They did. They were so positive and reassuring that when Anne asked me to remove the robe I was wearing, I didn't offer any objection. A moment later I stood before them in my pajamas, which were nothing more than a pair of Hello Kitty panties and a cropped tank top. Aside from Cassy and the girls in the gym locker room, it was the first time someone had seen me without a bra."

Abby squirmed in her seat. "That's intense."

"It was, for sure," I said, taking a drink. "But they weren't finished with me. I obeyed when Liam requested I remove my shirt. And when Anne asked if she could take my panties off, I said yes."

"Ah, now I see where your submissive upbringing came into play."

I nodded. "That moment of being so exposed was thrilling and nerve racking but also comfortable and welcoming. Cassy had told them she had shaved my special place and they fawned over how pretty it looked. Liam's cock was rock hard and Anne saw me glancing at it. She smiled at me and stroked it over his pants, which was the most erotic thing I'd ever personally seen up to that point. But they didn't force me to do anything. From their point of view, it was perfectly natural to be aroused by the human body and his reaction when I disrobed was incredibly moving. It made me feel...beautiful."

"After all you'd been through, I understand why this was such a special moment."

"Yep," I said. "They told me it was important to be comfortable with who I was physically and I believed them. As the months wore on, that's exactly what happened. Most of the time, whenever I visited, Cassy insisted I strip down to my panties and a tank top and I never objected. It felt wonderful. Later, we were often nude around each other and it felt completely natural. Outside of an ocassional compliment, the men never forced themselves on me, or really even took notice of me in a sexual way. The whole experience was so liberating from my real home life and I loved the Vatspalts for it."

Abby was shaking her head. "Good God, you'd never find such cosmopolitan people like that in Kansas." She snickered. "You might find a farm boy who would fuck his sheep."

Now I shot a raspberry. "Don't be gross!" I took a drink. "They also openly discussed sex and sexuality with each other and because it was so normal, I felt more mature whenever I was around them. I also began to understand that saving myself for the one person I'd have sex with for the rest of my life was completely unreasonable; the concept seemed so flawed. I spent a lot of time thinking and fantasizing about sex back then but it wasn't until much later that I realized the reason I was so interested: Sex and sexuality was a forbidden topic in my house."

Abby looked a little troubled. "That's how I was raised, too, and being monogamous always felt okay to me."

I patted her knee. "And yet here we are, meeting in secret after posting sexy profiles on a hookup site."

Pouting, she said, "I see your point."

I shared with Abby the evening I spent with Cassy and Louise and the roughhousing that led to the moment the older girl pushed her fingers inside me, marking another first. "Louise had shown us a cellphone video she'd taken of an encounter she had with four guys and it was exciting to watch."

"Four guys? You mean she had sex with four guys at once?"

"Yes."

"And she filmed it?

"Yep."

Abby looked away. "Gosh, that's hard to get my head around. And how old was she?"

I had to think about that. It had happened so long ago. "I think she was twenty-two. I know she was a year older than Cassy."

"Holy shit."

"Anyway, we were drinking and goofing off and ultimately started teasing each other, which turned into a wrestling match. Louise was naked when she pinned Cassy to the bed and started rubbing her special place over her sister's face. I tried to protect Cassy by hitting Louise with a pillow but she pulled me across her knees and held me down over her lap. She yanked my undies up my butt and was spanking and tickling me. I tried to fend her off but she was stronger. I may not look like it now, but I was a whisp back then, except for my breasts."

"You look amazing, Gwendolyn." Her eyes crawled over me appreciatively.

I waved the compliment off and Abby ordered us a margarita along with some chips and salsa. Continuing my story, I said, "Watching the video, along with being so helpless and...dominated, I suppose...really turned me on. Louise saw the wet spot on my crotch and started teasing me, saying I wanted to be gang banged. She worked her hand inside my underpants and pressed her thumb to my butthole. She said I had to stop squriming or she was going to push her thumb up my ass. That thought froze me and when she told me to spread my legs, I obeyed. She played with me down there for a long time and it felt wonderful. The next thing I knew, she pushed two fingers into my special place. She was the first person to penetrate me."

"Oh God, she..." Abby looked away, her cheeks glowing.

"What?"

"That must have been so embarrassing when Louise..."

"I wanted it to happen, Abby. She didn't force me."

Abby waved her hand. "No, no. Not that. Wasn't it embarrassing when Louise...when she tore your hymen?"

Now I understood. Shaking my head, I said, "I had been involved in activities like dance and gymnastics."

Abby chuckled. Now she understood. She said, "I tore mine horseback riding."

"Anyway, Cassy was only wearing a nightshirt and Louise went after her special place as well. She, um, really worked us over and I loved it." I also mentioned the afternoon I spent with Anne and Louise and the exquisite pleasure of being their bound plaything. "Initially, my first sexual experiences were with females, and it never felt awkward or uncomfortable. Cassy and I would often spy on her parents having sex, and as the year went on, I found myself being attracted to both genders; although my thoughts were dominated by the idea of a guy's cock inside me."

I shared with Abby the tutelage Anne provided me as I knelt in front of Lars and successfully took a man's cock into my mouth for the first time, bringing him to a climax strong enough to gag me. And, finally, I offered the details of my first time in unflinching detail. By the end of the story, I was talking fast and breathlessly. I had been wanting to share my past with someone for so long, that when the moment came, it flowed like a torrent.

Her eyes went big. "You're kidding me. Erick and Liam and Gustov? Three guys at once?" I nodded and sipped my drink, batting my eyes innocently. She said, "Your first time?"

"Yup."

She tugged a pigtail. "Jesus. In Kansas, we call that being sealed airtight."

I laughed. "Abby, I think that's what everyone calls it everywhere. In Sweden they call it korka igen, which means completely corked. I know it's not at all conventional but I don't regret it for a moment."

"Yes, but you were barely nineteen and Cassy's father and Gustov must have been..."

"They were both well into their forties, so was Lars, although he wasn't there the first time I had sex." I explained how the coupling took place. "They were very experienced and went slowly. They positioned me correctly and it was always understood we could stop at any time. It was loving and consensual and I still think fondly of it today. It was like a warm embrace, inside and out."

"Jesus," she said again. "Did it hurt? You know, when Liam was inside your....bottom?"

I shook my head. "Over the course of my...awakening..Anne guided me through a lot of firsts and had asked that I start playing with my bottom so that I would be ready when the moment presented itself. At the time, I was using a wine bottle...in my special place." I looked away but moved forward with the story, "to...stretch myself... so my first experience with vaginal penetration wouldn't hurt. Anne suggested I try inserting the bottle into my butt, which I did. By then, Cassy and I were spending a lot of time together intimately and I had been practicing with her for weeks, first with her fingers and then a stuffed unicorn that had a soft plastic horn. Her mom and sister introduced me to various toys, too. It got to the point that when I visited their home, Anne woud take me to her bedroom and fit me with an anal plug. I was required to wear it for the entire time I was in their home. If you work up to it and use lubrication, it's very pleasant. It's important that the man go slowly. You can't try and recreate a scene from an adult movie."

"Did they use condoms?"

I shook my head. "No. Anne and I talked about that and I told her I wanted to enjoy the experience of being filled."

"I was the same way," Abby said. "But weren't you worried about getting pregnant?"