So my boss is this older, beautiful woman. She's in her 40s, but has a fantastic body. I've always fantasized about her, but never wanted to risk doing anything stupid. In addition to my normal roles at the company, I take on a good deal of personal assistant stuff. While I hate that aspect of the role, she gives me the extra money we used to pay to an admin, so it's nothing to complain about.
As a result, I'm in her life -- fixing her phone, watching her pets, running her dry cleaning, etc. Several times during my iPhone repair, I've perused her photos in the hope of seeing her fine ass naked. A few months ago, I finally hit the jackpot. It was everything I could have wanted and more. Bare breasts. Waxed pussy. The whole 9 yards. When I found this, I was at her house working on putting together some furniture. I couldn't help myself, and grabbed a pair of her clean panties, jerked off in them, folded them neatly, and put them back in her drawer.
Today, I showed up at her house bright and early, and went to take some personal items of hers for errands. A few returns. Dry cleaning. Then she showed me a pair of jeans she ordered online and wanted to return. The fit wasn't right, but she had ordered the same cut and size. We were in a bit of a hurry, and with a casual, "Fuck it," she dropped her jeans she was wearing, and went to put on the pair that didn't fit well.
Maybe she thought I'd turn around -- this was the first time she ever changed directly in front of me -- or maybe she didn't care, but as soon as those pants dropped, my eyes locked on her perfect ass. I had walked behind this ass on many a staircase. I had jerked off in panties this ass had worn. I had seen nude photos of this perfect, heavenly ass. But finally getting a glance of her ass enveloped in the tiniest fabric thong was almost too much. She turned around and started, "See the jeans do not fit...", but then noticed my eyes, my jaw, and the growing bulge in my khakis.
"Can I help you?" she coyly asked. She stepped forward as her playful words hung in the room.
I'm a pretty witty guy, and relatively quick on my feet. I retorted relatively quickly, "No, I'm just looking," with a casual raise to my eyebrow, and devilish look in my eye.
She stepped forward. I reached for her. And it was all over.
She was in my arms in an instant. Our lips met, and our tongues seemed to dance for an eternity. I reached down and began to remove her jeans, pausing our kiss to attempt to deliver a funny line about her jeans looking better on the floor, but she quickly cut me off with a "Shut the fuck up and kiss me."
I did as I was told. After all, she is the boss.
We collapsed down into her love seat, and wildly began to tear at each other’s clothes. Before long, I was completely nude in front of her. She was down to her bra and thong.
She pushed me up -- I paused, wondering if this were the end and it were all too good to be true. She looked up at me, and took my hard cock into her mouth.
Now let me pause to say two facts of life:
1. The best head I've ever received was from a larger girl. Maybe it was because her mouth was bigger. Maybe it was because she had no gag reflex. But all I know is big girls give great head.
2. Older women come in a close second.
She began to give me the best, sloppiest, hottest blowjob of my 26 years on the planet. I could have finished right then and there, but I knew the best was yet to come, so therefore, I should not.
I pulled my cock from her perfect, angelic mouth, and gently pushed her back into the cavernous love seat. My lips met hers again, and I began to remove the faint pieces of fabric that kept me from her. As her bra clasp released, my lips, tongue, and teeth began to explore every inch of her neck, chest, and stomach. I returned to her breasts, loving, squeezing, and embracing her perfect nipples.
It was at this point she moaned something about giving me a raise -- I responded, "Should I take that up with HR?" -- a running joke in our small company.
As I gave her perfect, C-cup breasts the attention that they deserved, my hands moved down to her panties, and cupped her sex. She was so wet that my fingers glossed over when I ran them over the outside of her panties. I moved down to the floor, and got on my knees in between her legs. Her wetness soaked through the thin slip of fabric keeping my lips from tasting her, but I ran my tongue across her covered pussy all the same.
Lying back on the couch, she grabbed my hair, pulled my head up, and began to lift her legs up towards one side of her head. From here, I could see both her ass and pussy, covered in almost a thread of material. She began to slowly pull her panties off, elevating them skyward on her outstretched legs. Although she was finally joining me fully nude, my eyes never left hers throughout the entire "unveiling." Yes, I wanted to fuck her, taste her, enjoy her -- but I wanted her to know that I wanted one thing: her.
She draped her leg around my shoulder, gradually lowered her other leg to the ground, and slowly pulled my face into her pussy. Without breaking eye contact, I began to lick the edges of her labia, slowly and deliberately. I gradually moved more centrally, taking her moans as a cue to continue my exploration. Her eyes closed, her head rolled back, and I took my cue to fully embrace this beauty that lay before me. She tasted incredible.
As I continued my oral exploration, I let my hands run wild on the heavenly body that lay before me. I caressed her breasts. I ran my hands across her stomach. I fingered her wet pussy. My fingers trailed up to her lips and she graciously cleaned every drip of her cum off of my fingers. As I returned my hands back to my area of work, I began to squeeze and cup her enticing ass -- the culprit that began this wonderful, dream-worthy fiasco. Slowly I began to work one hand into her crack, all the while cupping her ass. As my fingers kept exploring, the tip of my middle finger finally found the delicate rosebud that was her asshole. I began to work my finger against her hole, as my mouth ventured further into her pussy.
Her moans grew louder, her breath quickened, and my face grew exponentially wetter until she began to vocally encourage my actions. By now, my finger was inside of her ass, and I had blissfully discovered that my knockout boss was an anal sex freak. As I pondered my luck, flicked my tongue against her clit, and continued to penetrate her ass further, she reached down with both hands and drove my face into her further. Fortunately, I had taken a breath prior, or else I might not have been able to come up for air. She began to yell encouraging expletives as her orgasm arrived. Her body contracted -- the tension my middle finger felt as her asshole contracted against my fully buried digit was exceptional.
I removed my hand from her ass, and joined her on the love seat, at least for a moment. She pulled herself close to me, kissed me deeply, and then moved up, out of our lover’s nest away from her cum soaked cushion. She led me by the hand, only briefly, then escaped my grasp and began to make her way up stairs. I followed her closely behind, making it well aware that I was enjoying my view of her legs and ass. Halfway up the stairs, she paused, and bent over. I came up behind her, and began to cup her perfect breasts with my hands, and pulled her upright. The back of her body met my chest, and I began to kiss her neck until I met her lips again. My hands continued to tour her body, feeling every inch of her beautiful, sun kissed skin.
She reached back, grabbed my cock, and began to guide it into her slick pussy. Our bodies joined and I slowly, passionately began to fuck her from behind, with one hand cupping her breasts, and the other rubbing her clit. The rhythmic noise of our bodies clapping against one another echoed throughout her spacious row home, and I was sure that her neighbors could hear at least our bodies crash and collision, of not our moans and screams.
We had spoken to one another throughout our passionate adventure, but quotes melted away into animalistic pleasure. A few remained, one of which I will retell for you now...
She turned towards me, met my lips, and casually told me as I fucked her from behind, "I've lusted for my body from the day I hired me."
I slyly responded, "I wish I made my move then."
She cooed, "I bet we can make up for lost time."
After those words left her lips, I removed my dick from her and spun her body around. I raised her into my arms, and carried her up the remaining stairs towards her bedroom. We paused at the top of the stairs, and I took a momentary delay against the wall to kiss her wonderful lips again. At this point, the feeling of having my boss pinned against the wall outside her bedroom was too much for me to handle. I took this opportunity to enter her yet again, and fuck wildly against her wall. Her nails dug into my back, and she moaned into my ear, “You’re all mine.”
I pounded away at her, “You get what you pay for.”
At this point, I heard her bed calling us, and transported us from the wall, through the doorway, collapsing into her down comforter. I climbed atop her, missionary position, and began to make love to my boss. Our encounter on the stairs and against the wall were instinctual, rough, and primal, but this moment was sweet, loving, and caring. Maybe it was the fact that I spent every waking moment of my life with this woman, serving her every need, forgoing family, friends, and loved ones to ensure her company, her life, and our livelihoods were ensured and taken care of, but in that moment I knew that what I was feeling was something far more passionate than the 20 something year-old fucks I enjoyed on the weekend.
Our movements slowed to a deliberate, meaningful pace, but the fucking we committed to at this moment was so real, so engrossing that I lost sense of time, meaning, and of the earth around me. Our breathing synced, I pulled back from her mouth, and stared into her eyes as if I had never looked at them before.
Against the backdrop of white sheets that our bodies used as a canvas, I realized I was fucking a masterpiece of a human that I had long desired. In a life full of letdowns, this moment exceeded my wildest expectations. Our pace quickened gradually, and she whispered that she was about to cum. My nods acknowledged her pleasure, and met her with the same words. She begged me to cum inside of her, and I was more than happy to oblige. By now, her hands were on my ass, guiding me into her. Our eyes locked yet again, and we began to reach a state of climax – together. With a few final thrusts, I collapsed into her.
Her hands grazed my body, as I lay beside my boss. She rolled to me, and I ran a fingertip down the curve of her side – her perfectly hourglass figure displayed in an exceptional manner. I pulled her close, and we both fell asleep together.
After we woke, the realities of what just transpired began to sink in. Realities often mean regret – but in this instance that was far from the case. She reached for her phone and sent a few emails – cancelled her afternoon meetings. In both a literal and figurative sense, “The train had already left the station.”
My mind was abuzz: What did this mean? What’s next? Insecurity began to join me taking a seat alongside inexperience and immaturity. Her voice quickly dashed those thoughts as she asked, “Are you ready for round two?”
She got up, and made her way out of the room. I watched her ass disappear down the hall. That ass…
I heard the hundred-year-old pipes begin to kick into action as she turned on the shower faucet in the bathroom down the hall.
I opened my mind’s journal and began to craft a mental note – “Dear Penthouse…” my conscious’ pen began to write. Her words broke my concentration, “Well? Do I need to ask twice?”
She certainly did not.
