tagMatureRoss the Boss Ch. 02

Ross the Boss Ch. 02


Ross the Boss Ch. 02: Eating Elena

"Ross , do you like Elena?"

Lorna's question roused me from deep thought. Or, at least, from staring out my window trying to think about anything other than sex. Ever since my erotic encounter with leggy Lorna, work just wasn't as focused. Lorna's husband had returned from his out of town construction job, so we had not had a rerun of our sexual encounter. She had gone back to her old habits of dressing conservatively, wearing little makeup, and maintaining her distance. Had our office encounter just been a dream?

Elena was the most friendly assistant in the office. She was a mature divorcee in her early 50s, who kept in terrific shape by walking, biking, and exercising. Her small breasts stood out proudly in the simple T-shirts she prefer to wear. Only the fact that she had magnificent large liquid blue eyes allowed me to look occasionally up from her frequently and easily aroused nipples. I liked to imagine that her excitement was the result of her having a fantasy of sex with me. I certainly thought of her enough.

In my dream, I come upon Elena in the copy room. She is wearing a skirt, flared out over her athletic hips. Her tight muscles flex under her clothes as she bends slightly to the copier. I stand and watch. Elena turns, and warms me with one of her terrific smiles. Her eyes don't meet mine. She stares down, at my obviously excited package, which tents out my pants. She giggles, turns back to her work, humming. She turns her head slightly. "If you want it, take it," Elena sings softly.

I step forward, placing my hands on her hips, lifting her skirt. Her hand reaches back to unleash my cock. I bend her forward. I pull her panties aside. She is already soaked. "I have waited so long for this, Ross," I dream she says.

Entering her from behind, I cup those perfect small breasts in either hand. She forces herself back on me . This sex , the culmination of months of attraction, is brief, intense. My fingers rolled and twisted her nipples through her shirt and soft bra. Her head twisted, her tongue searching for and finding mine. Her hips flexed back against me, meeting my thrusts. I broke our kiss to nibble her ear. "Yes, Ross, eat me, fuck me, take me!" Elena screamed. Only because this was a dream, no one heard.

Elena began lifting up and down, her hands gaining leverage against the copier. My cock filled her wetness, my balls got tighter. I kissed, then chewed her necked. My right hand was now up inside her shirt, squeezing her breast, twisting her nipple with savage intensity. Quiet Elena seemed to live way out along the pain/pleasure continuum, or so I dreamed.

Just as Elena and I simultaneously orgasmed in my imagination, Lorna's voice brought me back to reality. "Elena is complaining of a stiff neck. I notice how your eyes follow her walking down the hall. If you want her, offer her a back rub."

"What? Why? How come you're suggesting this?"

"Elena is a great person. She's been sour on sex since her divorce. I discovered that behind your shy mask lurks a fine passionate lover. Now that I get fulfilled at home, I think you two ought to please each other."

Hearing Lorna talk so openly was almost as shocking as her sexual enthusiasm the week before. My previously shy assistant was breaking down barriers. " Just do it," she advised.

I walked through the office. Lunch hour was quiet. Only Elena sat at her desk, typing. I stood silently, watching her flex and wriggle her shoulders, her glowing reddish blond hair bobbing side to side. I felt stirrings of arousal.

"Feeling a bit stiff, Elena?" I surprised myself by asking.

Elena twisted in her chair, looking at me over her left shoulder. "Oh, Ross, it's you. Yes, I've been typing this proposal all morning, I need to loosen up my shoulders I think."

"Have you tried chair stretches?"

"They stopped helping hours ago. If I don't get loose soon, I'll be at the chiropractor by morning."

" Well, I'd hate to see you miss that time off work. How about I try to massage your shoulders?"

"Sure, that sounds great." Elena , true to form, showed enthusiasm even in adversity.

I stood behind her chair, and started kneading the large muscles at the sides of her neck. I could feel them start relaxing. I worked my fingers out along her shoulders, easing her tension. As her shoulders relaxed, she sighed softly. I tried to work between her shoulder blades. She arched forward in her chair. "I have a chair in my office which might work better," I suggested.

"Good plan, Ross. The others will be back from lunch soon, so we don't want to distract them. But we can't take to long. I need to get this work done."

I followed Elena to my office, admiring the view , getting even more excited by the sight of her strong muscles rolling under her skirt. I quietly closed my door behind us. If Elena noticed, she did not object. We pulled an extra small chair out of the corner. Elena sat straddling the chair, facing the back of it. She leaned forward, her arms dangling over the backrest, presenting her back to me. I repeated the shoulder massage briefly, making sure everything there was still limber. I started working on her back. The fabric of her shirt bunched under my hand, reducing the effectiveness. I paused, still uncertain of how far this might go. Elena resolved my indecision, by calmly stretching, slipping her shirt over her head. She sighed, said, "there, that should make it easier," then settled back down.

I resumed, starting with a single strong thrust of my right palm, bracing her with my left hand on her shoulder. The move surprised Elena, who started upright in the chair, turning her head. This caused her hair to brush my already tumescent cock. When she turned, the shaft was clearly outlined in my pants, level with both her eyes and her lips.

"Ross! Its not fair if we just transfer the stiffness from me to you. Now that I'm relaxed, I better return the favour."

Elena swivelled the chair around, reached up and unzipped me. My cock, now fully erect, popped free on its own. Elena pumped the shaft slowly in her hand, then lowered her lips to kiss the head. " Elena, you don't have to..."I said, cautious of her ‘manhating' reputation.
"It's been so long Ross, but you're just the right man for this. Kind and gentle, but not looking for a commitment." With that statement, she stopped talking and began sucking on my cock. Elena's lifetime of experience had served her well. Despite a lack of recent practice, she took charge like a pro. She alternated between deep throating me and licking the shaft like a popsicle. Her tongue was soft and bathed me like no other lover had. All the while, her fingers kneaded my balls, gently demonstrating her own massage skills. Her glowing blue eyes shone up at me with a sweet twinkle. Elena was outstanding. I started massaging her breasts, first through her soft bra, then slipping them free. Her nipples , once erect, stuck out like erasers. Suddenly, I knew this had to be reciprocal. "Let's try the desk," I suggested.

Elena seemed to sense my desires, as evidenced by her slipping free of her clothing. She lay across the width of the desk, using her shirt to pillow her head. Her fingers played with her hirsute womanhood while I stripped. Her pubic hair glistened with moisture. I was shocked when she took her hand from her labia and licked her fingers. "I've learned to be my own best lover, Ross, including loving my taste. I hope you can stand the competition," she giggled, girlish at 50something.

I boasted myself on the desk, a knee on either side of her head, then slid down, feet sliding back, my cock aiming for her open mouth, my lips locating her dampness. My fingers pulled her thighs open, giving me my first closeup of her petals, as she opened like a flower. I started slowly, but her continued vigourous deep throating, alternating with her moans, signaled that this sex was not lyrical, or poetic in any way. My tongue and fingers picked up the tempo, loving her sex with no caution. When Elena started adding a bit of teeth toying with my cock, I followed suit. Her juices flooded my face, her thighs and the desk. I came first, having had a head start. She gagged briefly, but swallowed completely, continuing to lick my cock and balls, cleaning me as my erection subsided. Her attention, however, was diverted in a few minutes. My tongue bounced traced ever shrinking circles around her clit. I started using a stabbing cock like motion. My fingers toyed with the wall of her pussy- the mythical ‘g-spot'. It may or may not exist, but Elena sure liked it. Her hips started rising off the desk to meet my face. I grasped her butt to keep from being knocked off. I slipped my tongue up and down, over and under then around her clit. I sucked it right into my mouth and used suction to stretch it, initiating her orgasm. Only the office's soundproof walls prevented our coworkers from sharing the moment.

We lay there panting briefly, then realized lunch hour was over. Elena's absence would be noticed. We quickly dressed in silence, neither quite sure what to say. As Elena opened my door and started to leave, she finally said, "I waited a long time for that, Ross. You were as good as Lorna said. And unlike her, I'm always available."

As Elena let, I saw Lorna at her desk quickly sliding her fingers from her panties, her nipples stiff and her face flushed. Had she been listening at the door? Or just using her imagination? "Care to come in for dictation?" I asked.

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