Teenage slut, Adrian, offers her boss her anal cherry.
By the end of the first week, I had worked out most of the rules to Mary and Adrian's game. It was obvious they were alternating nights. So if I saw Adrian sitting in front of the living room TV, the moaning from the room next door would belong to Mary and her friend for the night. If I was late coming back to the townhouse and the living room was empty, I might hear them laughing and giggling as they shared details. During the day, I'd see them flirting with out-of-town trainers from other stores and I'd wonder who would be Mr. Lucky for that night.
Opening a new store in a new mall meant managing a team of peer trainers handpicked from across the country. As lead trainer, it was my job to manage the out of town staff. In an unusual move, the company had leased a big townhouse for the staff. Arriving during the construction phase, I had the big townhouse to myself and claimed the master bedroom with its whirlpool and jumbo sized master bath. The rest of the out of town staff would bunk dormitory style in the other three bedrooms. Most of the peer training staff were twenty-somethings excited to spend a week or two away from home "on business." It was my job to make sure they worked as hard as they played and make cuts every week. At the end of each week, I would send half the out of towners how until it was just me again. As the first week came to a close, I found Adrian and Mary on my shortlist of trainers to keep. At nineteen years old, they were too young to party in the bars after work. In the mornings, they were bright eyed and focused. In the evenings, they never complained about staying late at work.
Too busy partying, the rest of the out of town staff never caught on, but I did. While Adrian and friend used the room one night, Mary brought me up to speed with their game. "One and done," she said. When I suggested they would get a reputation, she laughed. "Not as if we'll ever see these people again." When I frowned, she laughed again. "Oh please, you know you'd do the same thing if you could."
"Maybe," I said with a nod and a grin. What I would or wouldn't do wasn't her business. She didn't need to know about the corporate trainer from the watch store who had spent the week with me before my team of trainers arrived.
Mary was the louder of the two, so if I saw Adrian in front of the TV, I would linger in the living room. It's where I found her late one evening after spending a couple hours drinking with the twenty-somethings. She asked why I didn't stay out. "Professional distance," I said, turning my attention to the TV in time to see the people on screen getting naked for a love scene. She was watching the crappy soft porn programs on late night cable. "Interesting choice of programs."
"All the good channels are blocked and I left my laptop in the room."
"And how would you know the good channels are blocked?" I asked, unable to hold back a grin.
She laughed. "Bet I have more porn on my laptop than you."
"Probably, since mine's a company computer. But then, I know the password to unlock the good channels," I said, unwilling to be one-upped by her. The idea of Mary and Adrian fucking every night in the room next to me was torture enough. Even if Adrian was exaggerating, the idea of her watching porn tugged at my libido.
"We should watch one," she said. In a supreme act of self-control, I shook my head. "Come on, Mr. B. I'm not underage or anything. It's legal to watch porn with me." I felt my self-control weaken. What if she 'accidentally' discovered the password to unlock the adult channels? Would she really watch one?
"Rental property passwords are always so easy to crack. I remember one place where the password was the unit number," I said, passing her the remote. She unlocked the adult channels and the TV filled with explicit sex. I headed towards the stairs. When she asked why, I explained, "It's one thing for you to crack the password. It's another for me to know you did. If those other guys come home to see me watching porn with you, there might be problems."
"I don't want to watch it alone."
"Funny, that's the only time I watch it," I laughed.
"If you let me watch in your room, you don't have to worry about anyone seeing me."
"True. But what am I supposed to do?"
"You can do what you usually do when you watch porn," she suggested, a sly grin on her face. Laughing, I started upstairs. Hesitating when she added, "We could do it together."
"Maybe the day after. Tomorrow's my night for the bedroom."
"Deal," I said, heading up to my room. After thinking about Adrian's invitation and listening to the sounds of Mary's lovemaking, I jerked off without the help of porn on the TV.
Adrian teased me about things the next day at work, starting by asking if I watched anything good on TV last night. "Just went to bed," I lied.
"Should have stayed in the living room with me last night. I almost got caught."
"Watching TV?" I asked, feeling my heart sink a little. I didn't need the rest of the staff telling stories about how I unlocked the adult channels for her.
"Well, what I was watching wouldn't have been as embarrassing as what I was doing," she said, flashing me a knowing smile. She looked around to make sure no one else could hear. "Watching porn always gets me so horny."
"Good to know," I said, trying to maintain my professionalism.
"We still have date tomorrow night, right?"
I laughed and was interrupted by a customer before I needed to give her more of an answer. That night, Adrian put on more of a show than usual in her bedroom. If I hadn't seen Mary sitting downstairs before I went to bed, I would have thought they traded nights from the muffled sounds of lovemaking. Instead, I knew it was Adrian telling her one night stand, "Yeah, fuck me" and "Oh fuck that feels good." She asked about it during a ride to work the next morning. "I wasn't too loud for you last night, was I?"
"Louder than usual," I said. No reason to pretend I didn't hear her.
"I was extra horny thinking about tonight," she said, though I assumed she was teasing. Playing it safe, I joined the over twenty-one crowd for drinks that night, hoping Mary might be done entertaining her guest by the time I went back to the condo. Or maybe I would found Adrian asleep on the couch? It wouldn't be the first time. Instead, I found her sitting on the couch watching a chick flick. Trying not to interrupt her movie, I headed quietly to the stairs. I made it as far as the bottom step when she said, "Hold on."
"What's up?" I asked, foot on the step.
"Just give me a chance to turn this off. I've seen it before," she said, poking at the remote. Heading towards me, she was all smiles.. "I was about to give up on you."
"How so?" I asked, playing dumb.
"Nice try," she said, passing me on the stairs. I followed her tight ass up the stairs, unable to stop myself from staring at how round and firm it looked inside her cotton shorts with the word "PINK" written across the ass. I noticed the lack of a panty line. Was she naked beneath those shorts or wearing a thong? Mentally, I voted for thong. Without asking, she opened the door to my room.
The master bedroom included a desk, a king-sized bed, and its own bathroom. The flat screen TV in the room hung opposite from the bed. Finding the remote, she sat on the foot of the bed, turned on the TV, and entered the code to unlock the adult channels. Through the walls, we could hear the sounds of Mary's lovemaking. "Adrian? Really, we shouldn't do this," I said, wondering how I was going to get out of it.
"Don't be a pussy, Mr. B.," she said, leaning back on her hands. Her t-shirt rode up, exposing her flat stomach as it pulled tightly against her small breasts. I noticed she wasn't wearing a bra. She glanced over her shoulder. "Is it okay if I get comfortable?" I shrugged, worried about what she meant by that. I felt my career on the line and felt out of control of the situation. I relaxed when she moved higher on my bed, positioning pillows and leaning against the headboard.
I sat at the desk, facing the TV, and tried to think of a graceful way out of the situation. On the TV was typical porn. A well hung guy and a pretty girl took turns going down on each other before they started fucking. "So much better than that softcore crap," Adrian said. I nodded, too busy trying to maintain my composure. Through the wall, we could hear Mary moaning as if she was auditioning for a porn movie. My growing cock was bent at the wrong angle. Not wanting to let Adrian see me adjusting it, I crossed to the bathroom. "Remember, shake it more than twice and you're playing with it," she smirked.
Behind the closed door, I adjusted myself, flushed the toilet and washed my hands. I took a couple deep, calming breaths before opening the door. I noticed Adrian's eyes had to move up my body before she looked me in the eye. I crossed back the desk chair, but she wasn't having any of it. "Come on, sit here with me," she said, patting the bed next to her.
"I can see from here."
"Don't trust me?" she asked.
"Actually, no. I don't."
"If you don't sit with me, I'm going to turn on gay porn," she threatened.
"Why not? More eye candy for me." When she picked up the remote again, I steered from the desk chair to sitting on the opposite side of the bed. Like I said, it was a king-sized bed, so there was still plenty of room between us. I stayed quiet, staring at the TV. After a bit longer, she asked, "Ever do that?"
On screen, the woman was getting fucked up the ass. I considered lying, but decided against it. "A few times," I admitted.
"Is it fun? I mean, it looks fun, but is it fun for her, too?"
"She always said it was."
"So just one 'she?'"
"No, more than one and more than once."
"Did they say was it was like?"
"Intense," I said, growing uncomfortable with the questions. "I don't know, I think it's an acquired taste."
"Can you keep a secret?" she asked. I nodded, hoping she could, too, otherwise I was in big trouble. "I really want to try that. Anal, I mean."
I sighed. This was getting to be too much. "Just find the right guy and take it slow."
"How does it feel for you?"
"Intense," I repeated, unwilling to say more. What was I supposed to tell her? That I love fucking a chick up the ass even more than fucking her pussy? Don't get me wrong, pussy is great; but taking a woman up the ass is about more than how it feels. Maybe it's just me, but I know, if she wants it up the ass, I found a freak to be with and I like that. Girls who like it up the ass are more fun than girls who don't. Just my opinion, but it's always been true for me.
"It's not as if I'm virgin back there," Adrian said. "I mean, I've used my fingers and toys back there and stuff. Just never, you know, went all the way with some guy."
"I don't know. Never found someone I could trust?"
I remember nodding and making some sort of affirmative grunt, as if to say, "Probably better that way." Meanwhile, my cock was straining against my jeans. Could she see it? Glancing down, I don't know how she could miss the large, swollen lump inside my jeans. Then again, I knew what I was looking at.
"You look really hard," she said, answering my question. Had she seen me looking at myself?
"Probably be something wrong with me if I wasn't."
"So, do you usually use lotion or what?"
I held my breath. What did that question mean? Was she asking how I usually jerked off? "For what?" I asked, worried.
"When you're doing a chick up the ass. What do you like to use for lubricant? I mean, I know you can't do it dry."
"KY or something like that," I said, knowing there was still of tube of it in the nightstand drawer next to her. It wasn't opened, but I had bought it just in case I needed it with the corporate trainer from the watch store.
"Ah, that explains this," Adrian said, opening the drawer and pulling out the unused tube. "Guess she wasn't into anal?"
"Yeah, something like that," I said, pissed that she snooped inside my drawers while I was in the bathroom.
"We could use it," she said, grabbing my hard on.
"Hey!" I said, squirming away from her.
She laughed. "Come on, Mr. B. How hard do I have to throw myself at you?" She clutched at her breast through her t-shirt, smiling at me. She pushed her other hand inside the waistband of her shorts. "It's why I'm here, you know?"
"Adrian, I can't," I said, staring at her and trying to remember why I couldn't. She was old enough and it wouldn't be the first time a corporate trainer had hooked up while on the road. Sure, it was against company policy, but that was to avoid lawsuits. While it was wrong for me to consider hitting on her, that didn't make it wrong for her to hit on me, did it?
"Sure you can," she said, pulling off her t-shirt. Adrian had small breasts, but they were perky and her hard nipples looked delicious. As I laid on the far of the bed, staring with surprise, she pushed off her shorts, too; revealing she hadn't bothered with a thong after all. This time, when she reached for me, I didn't bother to pull away.
Adrian was a nimble minx, crawling on top of me and straddling me. She pressed her pussy against the bulge inside my pants, squirming against it. "We can't," I said, even as my hands moved to her tiny tittles and my fingers learned her nipples were as firm as they looked.
"No, we just can't tell," she corrected before pressing her lips against mine. Looking back, I guess I reached the point of no return when I allowed her to follow me upstairs. Not that it mattered once she was naked. She pulled at my Polo shirt, working it off my head and pressed her naked chest against mine. Sliding off me, she kept her lips on mine as she worked the front of my pants. Once my jeans were open, she reached inside my shorts and pulled on my hard cock. "Mm, you feel good," she purred, breaking our kiss to pull off my pants.
Naked on my bed, we kissed as our hands explored each other's bodies. Adrian's nineteen year old body was slender and firm, a whisper beneath my eager hands. I grabbed at her ass, delighting at how firm her young flesh felt before she moved out of reach by kissing down my chest. Like in the porn movies we were watching, Adrian started our lovemaking by going down on me. As soon as her lips touched my cock, I learned she knew what she was doing. Without hesitation or shame, she licked and sucked me with the practiced, hungry need of a girl much more experienced than I ever imagined. Had I not wanted to take a turn going down on her, I might have let her finish. Instead, I pulled her away, rolled her on her back, and took my turn kissing down her chest, across her flat stomach, and not stopping until my tongue landed between her legs. Her young pussy tasted like heaven beneath my tongue.
Unlike her best friend and roommate, our next door neighbor, Adrian's cries of passion were soft and muted. But her softer moans didn't reflect the impact I was having on her body. I felt her small frame bucking beneath my tongue as her muscular stomach contracted with her orgasms. Her loudest spoken sound was a gasp and there were many of those as she came and came again.
"Fuck, you're good," she sighed, squirming away from me. "Fuck me."
Moving on top of her, I slipped my hard cock inside her sweet little pussy. She was hot, wet, and as tight down below as she was everywhere else. I felt her pussy clenching around my cock, tugging at it as I moved inside of her. She gasped again and I knew what that soft sound meant. She was having another orgasm. It happened twice more before my need consumed me. Holding on to her, I came inside of her, burying my face against the pillow to muffle my moans which were substantially louder than hers.
Breathing heavy from the thrill, I rolled off of her. Snuggling against me, she asked, "Do all old guys fuck that well?"
"Fuck you," I said, resenting her pointing out the near twenty year difference in our ages. I wasn't yet forty and didn't think of myself as old.
"It was really good," she said, rubbing my wet, spent prick. It had already relaxed into that neutral zone of being long and full, but not hard. "When I come back, I want more of this." After giving me a playful squeeze, she left to use my bathroom. It didn't take her long and when she returned to the bed, her hand returned to my cock. "I want more."
"Typical teenager," I said. Two can play at pointing out the age difference. At thirty-eight, my teenage years were far behind me, but seeing her fine young body naked got to me. I began to rise to the occasion.
"So, do you think we can do it that, um, other way, too?" she asked, caressing my hard cock.
"Are you sure?" I asked, feeling my cock growing stiff inside her hand. The harder I got, the less sure she looked.
"Will it hurt?"
"Not if we do it right."
"I don't know," Adrian said, eyeing my cock. "It looks big."
"His is bigger," I said, nodding at the TV where another porn starlet was taking it up the ass.
Still stroking me, Adrian stared at the TV. "Damn, I so want that," she said. A moment later, she handed me the tube of lubricant she had found. "How do we do this?"
"Get on all fours," I told her, not believing my luck.
Adrian crawled between my legs, facing the TV, and poked her firm, teenaged ass at me. "Like this?" she asked, looking at me.
"Perfect," I said, squirting a bit of the lube against her pink, puckered opening. "Now show me how you do it, first." After I pulled her hand behind her back, she understood what I meant. She rubbed her middle finger over her tightest opening. "Feels good, doesn't it?"
"It feels so wrong," she said, but she didn't stop. "Nasty knowing your watching me."
"Stick your finger inside," I said, rubbing my hard cock as I watched her middle finger press against her asshole. She pushed it in as far as her first knuckle. "No, all the way," I coached. "My cock is bigger and longer than that."
"Like this?" she asked, sliding her finger in to its second knuckle.
"All the way."
I heard her moan softly as her finger went as deep as she could.
"Mm, that's hot," I said, moving to kneel behind her. I caressed her ass, massaging and pulling apart her asscheeks. "Now do it with two fingers." She gave me a surprised look over her shoulder, but then she smiled.
"You're enjoying this, aren't you?"
"Sort of the point, isn't it?" I asked, playfully slapping her on the ass. "Now show me how you fuck that ass."
Adrian giggled, backed out her first finger, placed a second along side of it, and began working her ass a second time. My cock throbbed as I watched her and I was glad I already had one orgasm behind me. Reaching between her legs, I rubbed her pussy. She moaned again. "You're going to make me cum."
"Good," I said, rubbing her clit. "Keep fucking that ass."
"So good," she moaned.
"What's the biggest thing you've stuck up your ass?"
"A toy," she said, breathing heavy as her orgasm moved closer.
"A big toy?"
"Tell me you liked it."
"I did," she gasped. "I love fucking my ass!" And she came, louder this time than before. I smiled. When her orgasm passed, she slipped her fingers from her asshole. "Am I ready now?"
"Almost," I said, smearing lube on my cock before I put my fat, meaty thumb against her butthole. Slowly, I pressed it inside of her, feeling her body quiver as it slipping inside. When she began pressing backwards against me, I knew she was ready for the real thing. I replaced my thumb with the tip of my prick. "Just relax," I told her.
"Okay," she said, sounding nervous, but she didn't flinch when my cockhead touched her puckered opening.