Hailey’s Sexcapades Ch. 06: Hailey Helps Out

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Since I snuck into my neighbor Mr. Chapman’s backyard and got caught naked in his pool, my life had been a roller coaster of experiences. Who knew meeting my hunky black neighbor would turn into a sexual Renaissance for me? Not that I’m complaining, it just caught me by surprise. Now that we had forged an actual relationship, one that we officially upgraded to labeling, I wanted to do something special for him.

One could argue that letting my two best friends tend to his insatiable cock a few weeks ago was pretty special, but that was kind of a fluke. A fun fluke, but a fluke nonetheless. I wanted to do something just for him that showed my appreciation for his affection and hopefully surprise him a little. Every guy enjoys seeing his gal in something sexy, so I thought it might be fun to buy some lingerie, walk over to his house, and pretend I was a call girl or a stripper or something.

Should be fun, right?

I went to the local sex shop called Sinful Secrets and picked out a silky black and green ensemble with intricate lace that contrasted sharply with my pale white skin. The green matched my eyes, so all in all I thought it was a solid decision. An adorable, and entirely too expensive, pair of green heels caught my eye and when the cute little Indian lady behind the counter said they were half off, I simply had to have them. She even threw in fishnet stockings because my purchase was over one-hundred and fifty dollars.

“Don’t take this the wrong way, but have you ever considered using your ‘assets’ to make a little extra cash?” the woman behind the counter asked me.

“I’m not a stripper, if that’s what you mean. This outfit is for my boyfriend.”

“Oh, cute, he’s gonna love it. But I meant something a little more… personal. Have you ever heard of a glory hole?”

Since I don’t live under a rock, of course I had heard of a glory hole. I saw a few men loitering around a curtained off area to the back and wondered if she ran one. Not that I judge, I just wasn’t interested. “Thanks, but I’ll pass,” I said.

“OK, no pressure. If you change your mind, let me know.” She rang up my items and put everything in a discrete black bag for me. I knew I couldn’t just walk over to my boyfriend’s house in lingerie, so I stopped by the mall to look for something cute that was easy to take off, but still presentable to leave the house in. I found a black and green silk kimono that matched so perfectly with my lingerie that I couldn’t resist. I wouldn’t go to school in it, but I could go out for a short while and not look ridiculous.

I ran home, waited for my parents to fall asleep, and changed into my sexy new outfit that fit like a glove. I took some time to do my makeup, giving myself the smokiest of eyes and glossy lips, then tousled my hair a little so it looked like sexy bed head. After wrapping myself in my new kimono, which felt luxurious by the way, I left home and walked next door to my boyfriend’s house. A couple walking their dog gave me a strange look on the way over.

My outfit was a little more risque than your typical club outfit, but not outrageously so. My kimono covered all the important bits, but showed off my legs and cleavage. The fact that I have a generous bust with heaping cleavage made everything I wore look more provocative, even a parka. Not my fault. The heels and fishnets were probably what made the ensemble border on slutty, but I’d seen much worse when I’d been out dancing. Besides, I felt sexy as hell, so I didn’t much care.

I arrived on his doorstep and looked over my shoulder to make sure the couple that eyed me up were around the block before I untied the silk knot around my waist that kept the kimono closed. The soft fabric fell to either side of my body and exposed my curves packed into my new lingerie while still hiding my back from anyone walking by. When he opened that door, he’d get an eyeful I hoped he’d never forget. I knocked.

I placed my hand on my hip and puckered my lips a little, then tried to put on a sexy smirk. When I realized I couldn’t smirk and pucker at the same time, I went back to the pucker. Then I felt like I was making a duck face and wished I had practiced in the mirror before I came over. The deadbolt clicked, and I switched from smirk to smile to duck face, finally deciding on a big smile as the door opened.

A broad shouldered black man who was not my boyfriend stared at me. “Yo Chap, some white girl is naked on your doorstep,” he said over his shoulder. My eyes bulged, and I quickly wrapped my kimono around my body to cover up.

“Say what now?” I heard Mr. Chapman shout from the kitchen.

“Oh god, this is so embarrassing,” I said as my face turned a couple different shades of red. My boyfriend, who I still called Mr. Chapman because he seemed to like the air of authority it gave him, poked his head out of the kitchen to look.


“Hey hon,” I said with a meek wave, wanting nothing more than to crawl into a hole and die of embarrassment.

“Come istanbul escort in, come in,” he said, walking over to me in the doorway. “What are you doing here?”

“I wanted to surprise you,” I said.

“For what? What’s the occasion?”

“No occasion. It was supposed to just be a fun surprise.”

“Aw, you’re something else,” he said with a smile.

“Wait, this is the girl you’ve been tellin’ be about?” the broad-shouldered man who opened the door asked.

“Hailey, this is my friend Hotdog. Hotdog, this is my girl Hailey.”

“Hotdog? Really?” I asked.

“Dion is fine, we don’t need to go with Hotdog,” Dion said.

“His first day on the job he choked on a street dog and I had to give him the Heimlich. He earned the nickname when I told everyone back at the precinct.”

“C’mon man, you’re gonna embarrass me in front of your girl like this?”

“I don’t think anyone could be more embarrassed than me right now,” I said.

“What for? You surprised the hell out of me. Besides, that body is bangin’. Be proud of it,” Dion said. I flushed red again.

“Anyway, Dion just found out his wife’s been cheating on him. We were gonna go to the strip club to let off some steam,” Mr. Chapman said. Then his face turned to concern. “Oh, uh… unless you’re not comfortable with that?”

It was cute that he was willing to ask. Had I not come over he would have gone anyway, and frankly I didn’t much care either way. “I don’t care how you get your appetite as long as you come home to eat,” I said.

“Oh damn, I get it. I get why you like this girl,” Dion said.

“You sure? I don’t want you to feel-“

“It’s totally fine. You two have fun,” I said. I was disappointed that my surprise was ruined, but oh well.

“Nah, screw that. We got booze here and I wanna get to know more about Hailey,” Dion said.

“Really?” I asked, a little flattered.

“Hell, why not? You seem cool. I wanna get to know you if you’re gonna be part of Chap’s life.”

“I don’t wanna ruin guy time,” I said.

“Girl, sit your pretty butt down and tell me something embarrassing about Chap so I got ammo next time he pulls out that hot dog story.”

I hadn’t known Mr. Chapman long enough to have any embarrassing stories about him. Even if I did, I wouldn’t throw my man under the bus like that, even if it was just teasing. So we chatted about other things, mostly small talk. Birth places, job stuff, the usual. Since I was almost ten years younger than both of them, and still in school, I felt like I didn’t have many ‘adult’ things to contribute, so I kept to universal topics like entertainment and sports. I didn’t pay attention to sports myself, but my dad was always complaining about one team or another. I could keep up.

Dion was sweet enough to keep bringing things back around to me. I think he could tell I was still uncomfortable, and he was attempting to help me relax. We talked about my college experience so far, what my long-term goals were, and the scandalous story of how I met Mr. Chapman. I was proud of the cover-up story I had created where we accidentally got each other’s orders at a coffee shop and decided to sit down and chat. I never got that chance to tell it though because Mr. Chapman came clean right away. I guess it wasn’t really an embarrassing story for him. I was the one who got caught naked after all.

Since I’m rarely comfortable as the center of attention, I attempted to ask Dion lots of questions about himself. Eventually this got around to his wife, which I should have seen coming.

“I walked in on her bangin’ another dude in my own house. It was awful,” he said, staring at his drink.

“We don’t gotta get in to any of that,” Mr. Chapman said.

“I think it’s good to talk it out sometimes. If you want to talk, I’m happy to listen,” I said with a reassuring smile. In my, admittedly limited, experience with men they didn’t like to talk emotions. Maybe I was disarmingly cute, or maybe since he saw me mostly naked there was a weird sense that he owed me something, but eventually he opened up.

“Y’know, the worst part is that we haven’t had sex in months. Not even a handjob in the shower or nothin’. But she was gettin’ dick from someone else,” he said.

“That’s cold, man,” Mr. Chapman said.

“She flat out refused to have sex with me, but she was down to invite some other man into my house.”

“That’s so terrible and disrespectful. I’m sorry, Dion. If she was unhappy, she should have came to you and talked about it, not break your heart like that.”

“I just, like…” Dion’s voice trailed off. “We been married ten years. I helped pay for her college. I worked two jobs to make sure she could learn design. This is how she thanks me?” Then I heard a sniffle. I looked over, and Dion was wispy eyed. “I did everything for her, everything I could.”

“You’re a good man,” I told him.

“I tried so hard,” Dion said escort bayan before he turned his face away.

“He’s gets weepy when he drinks. I’ve got some cold water bottles out in the garage, I’ll be right back,” Mr. Chapman said, leaving the room to do just that. I scooted over on the couch and sat next to Dion, putting my hand on his back.

“It’s OK, she did you wrong. It’s not your fault,” I said.

“I know,” he mumbled, turning around and fighting back tears.

“It’s OK to let it out and talk about it. I won’t tell,” I said. His puffy eyes looked into mine. There was a scared vulnerability behind them. I opened my arms to give him a hug, and that vulnerability softened a bit. The silk tie that held my kimono together had come loose at some point, and it came open as I lifted my arms. He leaned in and wrapped his arms around my waist, bent down, and rested his head on my chest, cheek to cleavage. It was a little personal for having just met him, but he clearly needed some affection.

I wrapped my arms around his head and held him to my breasts, rocking with him silently for a moment. His arms were so big and my waist so tiny that he could reach all the way around my body. His fingers brushed my under boob, which he probably felt very well since my bra wasn’t padded. He lifted his face from my cleavage and shamelessly stared right at my chest. “Are these real?” he asked.

“They are indeed,” I said.

“For real?” he asked again, adjusting his hands in what he probably thought was subtle, but was a clear attempt to feel my under boob again.

“One-hundred percent Grade-A Hailey,” I said. He was getting pretty comfortable with me, perhaps more comfortable than I would have liked, but I figured he needed a woman to trust him right now.

“You’re lyin’,” he said. I sighed. Men have played this trick on me more times than I can count.

“Wanna touch them?” I asked. I wasn’t sure how my boyfriend would feel about it, but I didn’t see the harm. He’d cop a quick feel, I’d prove they’re real, and we’d never talk about it again.

“Oh hell yeah,” he said, unwrapping his arms from around me and taking two greedy handfuls of my generous bust. Though I expected it to be a quick transaction, I wasn’t entirely upset when he continued to knead them. My plans to come over and get busy were ruined, but my sex drive was still there. Getting ready for what I thought would be a passionate night with my man got me all hot and bothered. Plus, with how large breasts are, a massage always feels nice. “Lord Jesus, these are the best I’ve ever felt,” he said, pushing them together and squeezing them like stress balls.

“Thanks,” I said, arching my back to push my chest into his hands a bit, “but you better let go before Mr. Chapman gets back.”

“Does he make you call him that?” Dion asked, getting more adventurous now and brushing his fingers inside my bra cups, pushing his boundaries and slowly looking for a nipple.

“No, I just like to,” I said. I looked down as his dark hands fondled my pale skin. Why wasn’t I stopping him? I proved they were real, all I had to do was pull away. But I didn’t.

“Baby, I’m gonna be honest with you,” he said as one of his fingers brushed against my nipple. The electricity of the situation meant it was already perked up for him. “I haven’t been with a woman in a long ass time, and I would really, really appreciate if you did me a solid tonight.” I should have been offended, should have pushed him off me and told him I was taken. For some reason I didn’t. For some reason I just watched as he pulled the cups of my bra down and lifted my heavy breasts over the fabric, exposing them.

“I don’t know if Mr. Chapman would like that,” I said, my face hot and my voice dry.

“Like what?” a voice behind me asked. I whirled around, breasts out, and looked up at my boyfriend like a deer in the headlights.

“I, uh, I was just…” I stammered, but Dion jumped in.

“She was helping me get over my wife. You know how it is.”

“I see,” Mr. Chapman said, looking back and forth between us before glancing down at my exposed chest. We stewed in silence for a moment. I saw Mr. Chapman’s Adam’s apple bounce in his throat. “Hailey, are you cool with this?” he asked.

There it was again. Every time we got into a weird situation like this, which now that I’m thinking about it has happened a lot since I met him, he always asks me if I’m OK with it. Did that imply that he was always OK with it? That he just wanted my blessing? Or was he uncomfortable but didn’t want to disappoint me if it was something I wanted? Our relationship, while very intense for the short time we’ve had it, was still very new. We hadn’t gotten down to brass tacks on many things.

“I, uh…” I looked back at Dion, who’s face all but begged. He was even looking me in the eye, which impressed me given that my enormous chest was on display. Again, my response should have been a firm and Ataşehir escort polite ‘no’. My nipple now felt cold since he was no longer touching it, and that made me want him to. I knew he wasn’t leaving anytime soon, and my lust and emotions were just going to keep simmering until they finally boiled up at some point. Maybe I just needed to let it happen. “I suppose a quickie can’t hurt.”

Dion’s eyes lit up, then shot over my shoulder to Mr. Chapman. He shrugged. “You heard the lady.”

“Lord have mercy, this is gonna be great,” Dion said. I felt his hands slide around my waist and cup my breasts right in front of my boyfriend.

“Are you sure?” I mouthed silently, looking my man in the eyes. In hindsight, I wasn’t sure why I was asking for his permission. He put the ball in my court. Maybe I just felt bad for Dion and wanted to help give him the attention and release he so desperately craved. Maybe I secretly kinda wanted it too. Probably a little of both. Dion pinched my nipple, and I was unable to hold back a pleasured coo.

“You know me, baby. As long as you’re happy, I don’t care what you do,” Mr. Chapman said. He turned around. “I’ll leave you two alone.”

“Wait!” I said, “Can you stay?” It wasn’t so much that I was afraid of Dion, but I had just met the guy and wasn’t sure what he’d want from me. If my man was in the room, at least things would stay mellow, and there wouldn’t be any misconceptions about what went down. Mr. Chapman smiled and sat down, but stayed silent and watched as Dion clutched my bare breasts and nuzzled into my neck.

“You’re a lucky man, Chap. This girl is bangin’,” Dion said as he released my breasts and unbuckled his pants, tugging them down to his ankles and exposing his cock. “How bout a quick handjob, then we can all go back to relaxin’?” I looked down expecting to see a giant cock like Mr. Chapman’s and was surprised that Dion was more or less average. That made me appreciate just how unique my man was, and in some ways made me admire him even more.

Dion was already hard. I turned around to face him and took a second to mentally prepare for what I was about to do. He reached up with both hands and gently pushed my kimono off my shoulders, helping me out of it. My bra and undies were still on, but my breasts rested over the cups so he could see them. It also pushed them up a bit, which made them look nice and helped my confidence. I took a deep breath and reached forward to grasp Dion’s cock.

It throbbed so hard I could have taken his pulse. Both men watched in silence as I wrapped my fingers around Dion’s shaft and gently worked it up and down. Without lube it was a little clumsy, so I positioned my hand in such a way that I could use his foreskin to ease the friction. He moaned up to the ceiling and let my hand do its job for a bit. With Mr. Chapman behind me, I lifted my booty into the air and show it off for him. I couldn’t let Dion have all the fun.

As my affections sped up, my foreskin trick got more difficult. As if to illustrate the flaws in this plan, Dion would make uncomfortable faces each time I sped up. I wondered why he didn’t say anything, but figured he was probably grateful to get whatever he could. I felt my bra strap loosen and fall down my arms. I looked back and saw Mr. Chapman leaning over me, taking off my bra. As soon as my breasts were free, both men grabbed a handful.

“That should help a little,” Mr. Chapman said, pinching my nipple before sitting back down behind me. I noticed the usual bulge in his pants was thicker and more taut than normal. He was enjoying this. With friction being the problem it was, I leaned forward and let some saliva drip out of my mouth and onto Dion’s cock head, then used my palm to distribute it down his shaft. My hand glided much smoother now, and he relaxed into the couch even more.

As my hand slipped up and down his cock faster and faster, I noticed two things. The first was that without the support of my bra, my hand movements made my breasts jiggle in a way that had both men staring. Second, there was no way I’d be able to finish him without a steady supply of lube, or, in this case, my saliva. I wasn’t about to keep spitting on him over and over. It felt rude and wasn’t very efficient. My only other alternative seemed crazy though.

I looked up at Dion’s face. His eyes were fixated on my rack, but he chewed on his lip with such a hunger I simply knew I couldn’t let him down. I looked back at Mr. Chapman and saw him stroking himself through his pants. He wasn’t bothered one bit by what was going down. If anything, he was turned on by his mostly naked girlfriend jerking off his best friend. I looked down at Dion’s cock, which was almost dry again, and knew I had no other choice.

I lowered my face into Dion’s lap and took his raging hard cock into my mouth. “Oh no she didn’t,” he moaned out, and his hand immediately went to the back of my head to make sure I didn’t go anywhere. He tasted saltier than Mr. Chapman, but I wasn’t mad about it. I almost laughed when I felt his pulse throbbing on my tongue. This poor man was hornier than anyone I’d ever met, he desperately needed me to tend to him. I licked a few quick circles around his tip and then slid my face down till my chin rested on his balls.

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