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"Let me talk to Lisa first, okay?"
"Sure, but in the meantime, I want you to do something for me."
"Um, sure."
"Come with me," she told me while holding out her hand.
----
Denise led me by hand to the rooftop.
She didn't allow me to put my boxers back on, so I walked with a prominent hardon up the stairs. It was a good thing Tony and Lisa weren't at home.
As we walked around the hot tub and toward the ledge, I remembered the first time I saw Denise's naked tits in the pool. That seemed like a lifetime ago. Everything that happened after that was because I decided to join them in the chicken fight. I wondered if Denise brought me up here to remind me of that.
Denise guided me near the ledge, let go of my hands, and turned her body away. She placed both hands on the ledge and leaned forward, pushing her butt back toward me. She had pulled her dress down, below her butt, before we left the living room. With her dress so short and with her leaning forward now, I could see her pussy lips.
She looked back at me over her shoulder with a look of determination and demanded, "I want you to fuck me like this until you come."
There were so many things wrong with this request. I was intensely aware that I was naked on the rooftop on a bright afternoon. I couldn't recall standing naked with an erection in broad daylight like this on the roof before.
I glanced past Denise to look at the neighbors' houses. The left house beside ours was also three stories high, though they had a slanted and tiled roof instead of a flat rooftop.
Thankfully, their curtains were drawn at the moment.
The house on our right, at the farthest end of the pool from us, was only two stories. If we wanted more privacy, we could have gone to the right side of the roof instead. Denise must have planned this.
"Uh, won't the neighbors complain?" I nervously challenged.
"I've met them. They won't."
Denise was the only one who had met the neighbors within the first week of school. As far as I knew, five girls lived there, and I hadn't met any of them yet.
"Why here?"
"Because that's what I want."
"I'm really not comfortable with this," I told Denise.
"When you become my boyfriend, you can renegotiate all these, but for now, I want you to fuck me until you come."
"What if I can't?"
"Then you will keep going until you can," she replied, matter-of-factly.
"Denise..."
She lifted her dress above her hips again, and I watched her butt cheeks jiggle, freed from the tight-fitting dress. She was playing dirty... again.
"I really want you to fuck me like this. It's a deep fantasy of mine. Please?" Her voice softened at the word 'please.'
That made me soften my reluctance as well. I was also now tempted to fuck Denise in her green mini-dress. Looking at her pussy lips between her legs was too enticing. I wanted to feel my cock spurting inside her pussy.
I wondered what the 'me' on the night of the chicken fight would say if he knew the current 'me' was going to have sex on the roof during the day. He would probably think that the current 'me' had been impersonated by an alien... or perhaps mind-controlled by Denise. She seemed to have a strange power over me when it came to sex. I couldn't refuse her even if I wanted to.
I glanced again at the adjoining house, and the curtains were still closed. Hopefully, they weren't at home.
"Are you sure the neighbors won't mind?"
"Pretty sure," she replied. Then, as if reading my thoughts, she added, "Besides, they're probably not home."
I took a step forward and stood behind her. I gripped my cock and pushed the head slowly between her labia. I hoped I wouldn't have a panic attack now.
I almost regretted the moment my thighs smacked against hers as I bottomed out inside her. Denise moaned so loudly that I feared the whole neighborhood would know what we were doing. Almost. My arousal instantly took over, and I started to slide my cock in and out of her.
Denise screamed louder as I thrust. I felt more ashamed with each scream, but that shame only made me thrust and rock faster. Maybe, like Denise, I was a closet exhibitionist, or perhaps it was the naughtiness of it that was so thrilling. I contemplated that with each thrust as I felt her tight vagina hungrily swallow my penis.
It was so fucking unbelievable. I was having sex with Denise on the rooftop, in broad daylight, with her still in her dress.
I was expecting my anxiety and fear to take over at any moment. So I looked down, instead of at the neighbors' buildings, watching my cock appear and disappear inside her entrance. My favorite sight.
----
I reveled in Denise's pussy clenching tightly around my cock as I brought her to her third orgasm on the roof. I was starting to honestly believe this was one of Denise's fantasies.
Denise always came quickly but seemed to have come even faster on the roof. I didn't know how long we fucked on the rooftop, but after her second orgasm, I didn't care anymore. I was getting desperate to come.
When I still couldn't come, she put both hands behind her back. Then, like before, she told me to restrain her wrists with one hand and grip her hair with the other. Then she started her dirty talk again, telling me to use her like she was my personal slut. I was so absorbed in it that I hardly even noticed her announcing it to the whole world.
After a couple more thrusts, I felt the dam break, and the flood poured out of me. My body partly collapsed over her and Denise lying over the ledge, we both were still and panting.
---
Denise asked me whether I liked it whenever we tried something new during sex. For some reason, though, she didn't talk about the whole sex-on-the-roof thing at all.
After I had finally ejaculated inside her, we got into the hot tub and spent an hour cuddling in silence. It was as though we shouldn't talk about what we had done -- like two people having committed adultery and torn between guilt and how much they enjoyed the act.
Although I was grateful for it, I considered how out-of-character I had behaved once my arousal came down. I was surprised by my willingness to have sex on the rooftop. It wasn't even about my condition anymore; I was pretty sure most people wouldn't have sex so openly like that. I didn't think I was an exhibitionist like Denise, so I wondered if Denise had manipulated me from the beginning with the whole 'be my fake boyfriend' conversation.
Yet I didn't regret it at all. For reasons I couldn't comprehend, it was one of the best sex experiences of my life.
----
The following day, Denise surprised me again by not mentioning what we had done to Lisa. I thought Denise would gloat about it, but instead, she behaved as though we should keep it a secret.
After that 'fake boyfriend' talk with Denise, I started to realize how much I really liked her. I wondered if I was also falling in love with her. I could even imagine myself being Denise's real boyfriend. I would love that.
Thus, I became a little eager when I broached the subject with Lisa as we walked to school. I was afraid Lisa would say no, though, and I didn't want Lisa to say no. After I told Lisa what Denise had said about me being her fake boyfriend, she remained silent for a long time and considered it.
Finally, she said, "Okay."
A little surprised, I blurted out, "You're fine with that?"
"For now," she replied, "but you must promise me one thing."
"What's that?" I responded quickly.
"I want you to have anal sex with me first... before you do it with her," she insisted a little too firmly. "Promise me that."
I didn't know why Lisa had emphasized that. Objectively speaking, wouldn't it be better if I was more experienced first? I didn't object, though. It was a non-issue for me and likely a non-issue for Denise.
"Um, sure," I agreed.
---
Later, Denise and I were sitting in the kitchen, me in boxers and her in a white, lacy g-string. I recounted the conversation with Lisa, and Denise said she didn't mind that at all.
Out of curiosity, I casually asked Denise why Lisa would insist on that 'anal sex with me first' requirement. Denise said Lisa had issues but didn't want to elaborate on them.
"Um, so are we going to start now... the fake boyfriend arrangement?"
"For now, just start thinking of me like your girlfriend," Denise stated.
"Uh, sure, but what else should I do?" I asked.
"You can bring me up to the roof," Denise told me.
"N-now?" I uttered, stunned.
"First, you can tell me whether I should wear a dress," she replied.
I swallowed hard. Having sex with Denise in a tight dress was becoming my favorite thing.
"Um, whatever you prefer," I responded.
"I'd prefer my boyfriend to tell me whether he wants to fuck me in a dress."
I gulped again. I guessed now that I had boyfriend privilege, albeit a fake one, I should allow myself to enjoy certain things, right?
"I think your boyfriend would love that."
----
I was sitting on the couch in the living room when I saw Ezra walking out of Tony's room.
"Ken, can I talk to you?" Ezra said as we held eye contact.
"Um, sure," I replied somewhat cautiously. I would have preferred to enjoy my morning coffee alone since Sunday morning was usually the only time I could have the house all to myself and enjoy a little quiet before my housemates woke up around noon. I was surprised to see Lisa's elder sister in the house today. Sunday was the day we four housemates would have brunch together.
Ezra sat on the end of the couch furthest away from me. She leaned back and relaxed her body into the soft cushion, avoiding looking directly at me. I took that as an attempt to help me be comfortable with her presence first. She treated me like a cat -- always approaching me slowly, gently, and with caution.
She didn't need to do that, however. I was more curious about what was on her mind. I guessed it had something to do with anal sex with her sister.
I took the time to admire her long, slim legs and the swell of her breasts. She was wearing a loose red dress. It wasn't provocative by any means, but it hugged her body as she sat, emphasizing her enormous rack.
In terms of physical appearance, Ezra looked more like Denise than Lisa. If I didn't know them better, I would have guessed Denise and Ezra were the real sisters.
In fact, the three Kelton sisters looked very different from each other.
Like Denise, Ezra had a slim body with big breasts. Whereas Elsa, the youngest sister, had a big booty, relative to her petite frame, with modest breasts. The only thing the three sisters had in common was their green eyes, which they took after their mother. Even the colors of their eyes were different shades -- Lisa's were sparkling green, Ezra's were blue-green, and Elsa's were hazel-green.
I always wondered if the Kelton sisters each had different fathers. The Keltons were the most interesting family in high school. For one, they had their mother's maiden name. Second, Mrs. Kelton had three husbands. Strictly speaking, she was not triple married since polyandry (having multiple husbands) was not legally recognized. Yet that didn't stop her from living with three men as her husbands.
I wondered how three men were willing to share a woman like that. I also suspected that having three fathers was why the Kelton sisters were so comfortable with non-monogamy.
If I were Lisa, I would have been anxious to discover who was my biological father. To my knowledge, Mrs. Kelton made it a point not to find out who were the real biological fathers of each of her daughters. The sisters also didn't seem to care.
It was only after I looked Ezra in the eye again before she started speaking. "Are you comfortable if we start with anal sex today?"
"With you?" I asked.
"With my sister."
"Oh." I paused. "But you'll be there, right?"
Ezra was the most adventurous of the three sisters. Not just sexually speaking, but that was the most obvious way. Unconventional sexual practices and relationship arrangements were always her interest. Even in high school, she experienced a wide variety of relationship structures. First, a boyfriend, then a girlfriend, then two girlfriends, then two boyfriends, then as a third with a couple. Last I heard, she had three girlfriends.
"I will be there," Ezra replied. "Are you comfortable with that?"
"Um, sure." I wasn't certain how I felt about Ezra being present. Lisa had mentioned Ezra would be helping her at the start, but it was only now that it had dawned on me what that actually meant.
"I don't want you to freeze up, Ken. Anal sex can be uncomfortable and terrifying for the first time, so it's important for you to be fully comfortable and relaxed around me."
"I'll try not to freeze up."
"I have a suggestion on how to avoid you freezing up."
"How?"
"We can try having sex together first."
"Uh, is that necessary?" I was more curious about her reasoning rather than opposed to the idea. The Kelton sisters were all physically attractive. I didn't mind having sex with Ezra.
Apart from Lisa, I was most comfortable with Ezra, at least intellectually speaking. Ezra had always been interested in psychology since she was young. I wasn't surprised to hear she wanted to be a sex psychologist, a sexologist as she put it.
In high school, she would frequently talk to me about my condition. Lisa and Ezra were gentle and patient with me, but Ezra was more capable and tolerant when I was being 'difficult.'
"Lisa thought it would be a good idea," Ezra stated. "I do, too."
"Then, after that, I would, uh, have anal sex with Lisa?"
"Once you're comfortable having sex with me, we will start by having a foursome to get everyone relaxed and satisfied. Then, if you're still comfortable, you can start anal sex with Lisa."
"Foursome?" That had my anxiety stirring.
"The three of us, plus Denise."
"With Denise?"
"Denise wants to watch. Denise is also helping Lisa to clean her butt before anal sex."
"Clean her butt?"
"Are you asking about the purpose of cleaning her butt or how she's going to clean her butt?"
"Uh, actually, never mind that," I countered. "You don't have to answer the question."
Ezra smiled a little. "If you're going to help Lisa and Denise with anal sex, then you should at least know more about it first."
"I'm afraid I might freak out when you get into the specifics."
"Yes. That's why I didn't want to bombard you with the specifics, at least until you're more comfortable with it first."
I nodded. "So are we going to, uh, have sex now?"
"I'm surprised you're not reluctant to have sex with me at all."
"All this is to help Lisa, right?
"It is," she replied. "Are you no longer afraid of physical intimacy?"
"At least not with Lisa and Denise."
"You don't feel anxious at the thought of having sex with me at all?"
"Um..." I stammered.
At that moment, I fully understood the phrase 'don't jinx it.' Ezra's question suddenly made me feel a little fear of being intimate with her. It was an uncomfortable feeling in the gut that kept growing.
"Are you starting to feel a little anxious now?" Ezra gently checked.
Shit. The anxiety was rising. "Um, sorry, I..."
I took a deep breath and tried to calm down. If all these were to help Lisa, I didn't want to blow it.
"Don't be sorry. Take your time," Ezra soothed.
"This sucks," I admitted while waiting for the anxiety to pass.
"Here's the thing about fear. It's okay to be afraid," Ezra said. "The trick is not to fight it."
"Is that how you got over your fear of heights?" I asked.
Another thing the Keltons had in common was their fear of heights. They called it the Kelton's Curse. In high school, Ezra decided she didn't want to live with the curse anymore, so she designed a series of 'practices' to help herself overcome it. Those practices eventually gave Lisa the idea to help me overcome my fear of intimacy.
Ezra would participate in the most fear-inducing, adrenaline-pumping activities. These included rock climbing, bungee jumping, skydiving, riding roller coasters, and standing on the tallest building in school and looking down. All were designed to have her face her fears.
"Physiologically, I have never gotten over it," Ezra said. "My heart still races. My hands and feet start sweating. I feel tingling in my feet, my neck, and my spine, but I've learned to stop fighting it. I've learned to overcome it."
"How?" I asked.
"Exposure therapy is great at the start, but over time, it's about letting your mind know that nothing bad will happen. My body is still afraid of heights, but once I get into it, my fear is replaced by excitement."
"So you're saying I should keep having more sex?"
She smiled a little. "That's a good start. That's what I recommended for Lisa to do with you, and I can see it's been working for you. Your fear is replaced by arousal and sexual excitement."
"Is that why she keeps asking me to have sex with more girls?"
"That's one of the reasons."
"What are the other reasons?"
"Never mind that for now," she resisted. "I have a suggestion on how we can proceed if you're open to trying."
"Um, sure."
"I'm going to straddle you. I want you to penetrate me, even if it's uncomfortable for you. Don't fight it. Just go along with it first."
I gulped. "Okay."
She stood up and reached underneath her dress to take off her panties. I could tell she was doing this for my benefit, replacing my fear with arousal. My cock started to rise in anticipation as I watched her panties drop out from under her dress and onto the floor. A red thong, the same color as her dress. Sexy.
"Normally, I would recommend that you close your eyes, but I think it would be useful to see what happens when you watch me."
I nodded.
She knelt on the floor in front of me, hooked her thumbs inside the waistband of my boxers, and pulled them down. I lifted my butt to allow her to slide them down my legs.
By the time she got up and straddled me, I was already anticipating having sex with Lisa's sister. I didn't even flinch when she reached under her dress, gripped my cock, and pushed it inside her.
"Are you still experiencing fear?" Ezra asked as she straddled my lap, my cock sheathed fully inside her.
"Um, yeah."
"More fear than before I straddled you?"
"I think so."
"Do you feel like there are bugs running up your skin?" she examined with her hands on her hips.
"Not now."
"What do you think is causing the fear?"
"You know, the usual." I had a long list of what was causing that fear. According to Dr. Lee, it includes social anxiety, general anxiety disorder, low self-esteem, strict parents, religious upbringing, abandonment issues, and separation anxiety. In high school, I frequently talked about these with Ezra.
"Is there anything specific right now?" Ezra asked.
"Not particularly... it's more like I feel... very naked... if you know what I mean. Like the fact that we're naked like this in the living room."
"I know what you mean. You feel vulnerable and exposed."
"Yeah, like we're not supposed to be doing this."
"Is it 'we' shouldn't be doing this, or 'you' shouldn't be doing this?"
"I think it's me."
"Interesting. Would it help if we went to your room?
"Um, I think it would."
"Why don't we just talk for now like this to see if you can get more comfortable after a while."
---
"Do you feel unworthy of having sex with me?"
"Maybe. I'm not sure," I answered, "but I wouldn't think a guy like me would be having sex with a girl like you."
"One thing you need to realize is everyone has their flaws. Everyone is weird in their own ways. No one is perfect. Even Tony, Lisa, and Denise... if you stop idolizing them and learn to look at them in an unbiased way, you'll realize they all have issues."
