Maggie Turns 50 His Side

Turning Fifty - the other side

It had been a lousy Wednesday. The weather was lousy, it seemed that everything in the work environment had been lousy, the stock market was lousy, my personal life was lousy.

Ronnie was sort of a flash of light as she swung into my office that afternoon, “got a second?” was her introduction to a conversation that usually goes on for much more than a second. Ronnie was one of the truly hot women that worked in my company. It had taken all the restraint I had within my 56 year old body to not come on to her when I bought this company three years ago. She was easy to get to know, outgoing, sexy and often aggressive, which made her ideal for her position as our media relations vice president. I didn’t want to do anything to endanger losing her because I was horny.

I can remember my first day in the corporate offices that Ronnie had swung her hip into my office (yes. that is how she did it) with her “second?” question. She most often wore soft feminine flirty dresses which were conservative enough to make her appearance acceptable in most board rooms, but revealed enough of the wonderful body beneath it to make her welcome at lunch, cocktail parties, dinner and whatever may follow. The best part for me was her mind. She was brilliant, intuitive and smart in every social and business sense.

She brought me a full accounting of what she was involved with, what the direction she was following with the various media, who were our enemies and our supporters. A folder had been prepared for me listing whom I should speak to and what about. After almost 45 minutes of our “get acquainted discussion” we were deep into discussion when Ronnie popped up from her chair and leaned over my desk to point out an item in one of the papers. Her dress had a loose neckline that bloused down slightly when she was standing or sitting, but when she leaned over as far as she did it hung away from her in such a way that allowed me to get a full view of her breasts. I was completely non-plussed, losing all ability to concentrate on what she was pointing out. Her creamy smooth breasts were barely contained in a lacy bra that left very little to the imagination.

My cock surged having had little first hand stimulation of this sort for several years. Fortunately for me, my desk concealed the physical reaction, and Ronnie continued right along as if nothing had happened. I was never sure if she did this deliberately or accidentally.

Fortunately, we became friends. We even discussed the way she dressed in the office and her leaning over my desk and she admitted that she did it deliberately to get a reaction, to see how I would treat her! Both of us agreed that it was best to not mix business and pleasure, which was responsible for our becaming very close friends.

She would often come in my office to hear about my miserable weekends, cajoling me to get out and meet people. After brow beating me she relished in whetting my appetite by telling me many salacious details of her weekends, to the point of telling me she had a “boy-toy” that she used strictly for sex when she was between more serious boyfriends.

I envied her sense of confidence with the opposite sex. Following the end of my disastrous relationship two years ago I had not even tried to date. Some blind dates, set-ups by family members who thought I should get out had been less than fun. Perhaps comparing them to Ronnie or the vision of what Ronnie would be like in those situations had been the problem.

Today was another of her efforts to change my lack of a social life. “You are taking me and a girlfriend to dinner on Friday!” was the first thing out of her mouth as she sat forcefully in the chair adjacent to my desk. Her exposed knees, jutting breasts and the thrust of her jaw said ‘you do not have a choice in this one buster.’ I was actually more than willing to accommodate her, my weekend looked like it might be another of those clean, straighten, read reports, think about going out to dinner alone, more cleaning and more straightening, more reports, only to find that the weekend was over and I was just going to go back to work. I had dreaded the thought of Ronnies bright face and luscious body cajoling me on Monday morning even more than the boring life I was leading.

Not wanting to appear too easily ‘managed’ I challenged her in a mocking way. “And why would I want to go out with the two of you to dinner on Friday? Besides, I may have plans!” This took her a bit off guard, since for weeks when she has asked me about my weekend plans and I almost replied in rote “no plans.”

“Well, she is recently divorced, hasn’t started dating yet, is sexy and smart as hell and it is her birthday. I think you would be a great birthday present from me to her. And besides, what kind of plans do you have?” her voice was almost angry, but also questioning the fact that I could actually have plans.

I couldn’t restrain my laugh, snickering at her anger and quickly relenting “Sorry, I was just kidding, I don’t have any plans .... but the look on your face when I said that was priceless. Ok. so tell me more about this ‘recently divorced, dateless, sexy, smart’ lady. How old is she going to be anyway?”

“Frank, your sense of humor can be very maddening, no wonder no woman wants you ...” she joked, knowing full well that she had confided that if I had given her the slightest of encouragement she probably would have ‘fucked my brains out right there on my desk’ - her words - the first day we had met. She said she admired the way I had kept in shape, although not overly muscular, she loved the gray in my hair, even though she went to great lengths to make sure none of hers ever showed. This was one subject that I never understood about women!

“She is turning 50 on Friday” Ronnie continued. “I want her to have a good time, and I mean the best time the two of us can show her!”

“Oh, are we talking a menage-a-trios?” I was startled since Ronnie had been very frank about her sexuality and hadn’t expressed any interest in multiple partners, either male of female!

“No silly, I am bringing along Stewart! We will just see how the evening goes with you two and will be more than glad to get out of the way whenever I think it appropriate. Frank, I want you to show her a great time, flirt with her, kiss, ..... hell fuck her if you want to and she wants you to!”

Part 2

“Damn Ronnie ....” I almost exploded, “here you are talking about my fucking a lady I don’t even know her name! Are you trying to set me up, or turn into a pimp?” My expression was pointed but joking at the same time.

“Details Frank, you always are one to worry about details aren’t you?” she joked back at me as if just having a chance to fuck someone should be enough. She knew that I was not necessarily interested in just having sex, although that was a great part of a relationship, I couldn’t have a ‘girl-toy’ like Ronnie had her ‘boy-toy’ for some reason. It just didn’t seem to be good without some sort of mutual interest, commitment.

“Her name is Maggie Malone, she was a college roommate of mine. She is very smart and has unfortunately hit a very bad time in her life, personally and professionally. You probably remember her from some of our parties?”

I couldn’t place the name, “What does she look like?”

“Well, she is very attractive, I saw her at he gym a couple of weeks ago, and despite her age and a couple of kids, she looks great! Maggie is about my size, slightly larger breasts I would guess, great looking legs, and since her divorce I hear she hasn’t really dated much if at all.” Ronnie had a way of comparing other women to herself that I liked. “She has short redish hair, was an academic standout at school, even I had trouble keeping up with her. It simply amazes me that her company let her go with a downsize.”

“Oh, what did she do?” I was wondering what we would have to talk about except our mutual friend Ronnie and he match-making prowess.

“She was vice president of human resources if I remember correctly. Quite good at it from the word on the street, but she hasn’t been aggressively looking for a job. She got a good severance package and a good divorce settlement, so she isn’t in any hurry.”

“Well, I will make sure I don’t try to hire her here, I don’t think I could stand to have two sexy and available, smart women working here that I couldn’t hit on!” I joked.

“Hey, those are your ground rules, not mine!” Ronnie retorted, “I would gladly screw you!” She teased. “Besides, I want you to have fun, I want Maggie to have fun, so maybe you can be a bit more aggressive and I think the two of you might even hit it off. Sex on a first date isn’t unheard of in this day and age you know!” She was again badgering me, but the added frustrations of the past few months with work and the lack of any kind of personal life made me begin to think about it.

“Just be at the bar at the Matador at 7 on Friday night. I will introduce the two of you!” She said as she elongated her body rising from the chair beside my desk. “If I know the Maggie of old, she may be very receptive!” she intoned in a husky voice, her back arched in a suggestive way as she pointed her breasts at me. Her nipples were excited and protruding against the fabric.

“You are actually excited by the prospect of getting me layed aren’t you!” I challenged her.

“Of course, I am also a voyeur, and just the thought of you and Maggie fucking has me wondering when I can get to Stewart’s place, or should I just go to the ladies room and masturbate?” She responded, looking just the slightest flushed by either or both ideas. “But if you and Maggie are in the mood, I’m sure Stewart and I would love to watch!” Her face was almost aglow with the idea. She turned briskly toward the door, swirling her skirt and her hair in a synchronous wave of dismissive flirtation.

“Get out of here and get some work done! I’ll see you Friday night!” I had to get in a last word, but her glance over her shoulder was sultry enough to mean ‘fuck you Frank!’ without saying a word.

The rest of my day, Thursday and Friday was consumed with imagining a red headed Ronnie; both clothed and uncloted. What would she be like, what would she think of me, would we find a mutual interest strong enough to go beyond a courteous good night kiss? I mulled Ronnie’s admonition to be more aggressive. Thursday night came with the amassed anxiety regarding the meeting on Friday evening and sexual frustration associated with the fantasies that Ronnie always caused, but this recent incantation she created was causing me to be almost constantly aroused. In order to fall asleep I had to masturbate to relieve the tension.

Friday was a blur of meetings beginning with a breakfast with several leading executives. Normally I look forward to this group of friendly guys that share information, and business. Today it was just a time filler, my mind on the evening and nothing else. Other activities throughout the day were equally mundane and hectic. I saw Ronnie only from a distance, but even so just seeing her seemed to send sparks through my body that all culminated in my genitals which tingled in anticipation of what I wasn’t exactly sure.

I left work at 5:45, a bit later than I wanted to, and rushed to my apartment. The cleaning people had been there as I had requested and everything was perfect. I’m not a neat freak, but just in case I wanted the place to look nice. I removed my clothes and hung up my suit and tie, threw my socks, underwear and shirt in the laundry and stepped into a steamy shower. I shaved closely, contemplating what to wear. The Matador was one of the newer trendy places, but was very ‘upscale’ which meant a suit and tie. I was more concerned with what else to wear. I had gotten into wearing thong underwear for my own edification, but wasn’t sure what women would think of it. Ronnie said she loved it, and often complimented me on how good my ass looked through my trousers ‘no panty lines’ was her joke. Then I decided that I was going to take Ronnie’s advice and go for it this evening, so I carefully shaved my crotch, hoping that if I did ‘get lucky’ that she would enjoy my shaved member and balls. My slightly extended shaft and tight balls made it easy to even reach the hard parts.

Dressed and out the door in an hour, I was in my car and was in the bar five minutes before the appointed time. Ronnie was already there, but was alone as I walked up to her. “Hello!” I said and put my arm around her waist. She snuggled her warm and soft body against me and gave me an incredible kiss! Her breasts were obviously not encased in a bra and I could feel their weight against my chest, her abdomen pressed into my crotch causing my cock to jump to attention. The kiss was totally un-business like; soft, easy and wet as she opened her mouth and invited my tongue briefly.

She pulled away a few inches “wow, I think you are ready for this evening!” again nudging her belly against my now semi-erect cock. I smiled broadly as I glanced down at her breasts which were vividly outlined by the smooth fabric of her red dress, her nipples prominently displayed. “So are you” I said with a sing-song voice. “I hope Stewart is up to it!” I teased.

“Oh he always is!” was a declaration made in a husky and wanton tone that I had never heard from Ronnie before. “You stay here at the bar, Maggie should be here any second, I haven’t told her about you yet!”

I must have looked like a ghost, “She will like you, I know she will ....” was supposed to reinforce my confidence? Then she grabbed my cock, standing between me and everyone else in the bar shielding her hand from view “just keep thinking about fucking her with this!” she said and stepped away, leaving me speechless for the first time in our relationship.

Ronnie hadn’t stepped five feet down the bar when this beautiful red head walked up to her and gave her a huge hug. Our eyes caught each other in an instant as she looked over Ronnie’s shoulder. She was indeed beautiful, her complexion a bit more fare than Ronnies, her features not as bold but a very pretty mature woman. The contact between us wasn’t just a brief glance, but almost a stare. I could hear Ronnie saying how glad she was that Maggie has showed up. Maggie responded almost as if she were talking to me with a “me too!”

The bartender arrived and I ordered a single malt scotch on the rocks and told the bar tender to put Ronnie’s and Maggie’s drinks on my tab. My gaze wandered back toward Maggie, and she was now sitting on a bar stool on the far side of Ronnie looking directly back at me. Maybe Ronnie was right, this was going to be a special evening.

Our drinks were served at about the same time that Ronnie signaled toward a young man that had been sitting at a table near where I was standing. He walked up to Ronnie and practically melted his body against hers. I guessed this must be Stewart. He must have been a good 20 years younger than I was, and I guess that made for the boy part of ‘boy-toy.’ Ronnie made the introductions and Maggie seemed as bemused by Stewart as I was. But based on Ronnie’s randy nature this evening, my guess was that Stewart would have all he could handle with her tonight.

The maitre de approached Ronnie and as they were getting up from the bar she signaled me to join them. I followed behind as they were led to our table, and when Maggie went to sit down I helped her with her chair. For the first time I could see that she was very provocatively dressed. The black was very flattering with her skin and hair color, her trim figure was melted into the tight dress, with a very low slung back that almost showed the top of her cute ass, I wondered if she had on underwear, since it was obvious that she had on no bra; the front was open to her waist as well, but held together with a shoestring that allowed about a one inch slit of skin to show through.

Ronnie smiled as Maggie turned to thank me, realizing that I was the same man she had been making eye contact with in the bar. “My birthday present to you. This is Frank Holiday, my boss. He’‘s paying for tonight. You can fuck him or not that isn’’t part of the deal.” Ronnie was always so subtle about things!

“Go away if you can’t be more polite about this,” I scolded her! “Let me get to know Maggie and then you can be your normal insufferable self,” Maggie was laughing as Ronnie feigned insult, but there was also a glint in her eye and a slight blush on her cheeks either in excitement or embarasment. I was going to try to find out.

We ordered wine for everyone, Stewart was obviously busy either playing with parts of Ronnie’s body in a less than discreet fashion, or putting Ronnie’s hand in his lap. Ordering food, trying to remember the parties that both Maggie and I had been at, learning a bit about each others work or at least Maggie’s last work dominated the conversation for a bit.

The band started playing before our meal was served, and Stewart and Ronnie were all over each other as they took the floor with a few other couples. “Do you like to dance?” was one way to get a better look, or even a better feel for Maggie’s body, although I had been perhaps a bit more bold than usual glancing down at her breasts as we were chatting. She appeared to enjoy the attention and once or twice had pressed her breasts together making her cleavage even more prominent in the gap of her dress.

“I love to ...” was her response and then she laughed out loud! “What is so funny?”

“Ronnie called and invited me out. This is my birthday and my official first appearance as a divorced lady. Suddenly it just seemed funny.” She was getting up out of her chair, holding my hand as we were headed for the dance floor.

I thought this may be overly pushy, but decided that I wasn’t going to worry about that this evening and I pulled her to me and kissed her. It was similar to the kiss that Ronnie had given me earlier. Her lips were soft and yielding to mine, they parted ever so easily allowing my tongue to gently caress her lips, the lower and then the upper.

She was staring back at me with desire “Happy Birthday Maggie and may there be many more kisses before tonight is over,” was barely a murmur from my throat, which was dry because I was so nervous and at the same time excited.

We danced, looking at each other, not touching much at first, but after a few seconds she edged forward and pressed gently pulled me against her forehead which rested gently against my cheek. We didn’t say much more. Our bodies were doing all the talking. Her full breasts were pressed against my chest, and when I pulled her abdomen against my crotch where my now full erection was splayed against my belly, I heard her sigh and slowly rotate against me.

Dinner and drinks seemed a blur. Stewart was decidedly not a part of the conversation, and Ronnie only filled in when we couldn’t remember a mutual interest or time that one or the other of us couldn’t remember. It was a dinner for two, with some slight coaching from the sidelines.

Stewart and Ronnie were obviously in need of a less place to continue their evening, and I finally told Ronnie “get out of here, I will take Maggie home.” My motives weren’t exactly just to satisfy Stewart’s and Ronnie’s needs, but perhaps those of Maggie and me as well. I had found out at some point that Maggie had taken a cab to the restaurant. I certainly wasn’t totally comfortable with Ronnie knowing when we left and where we went.

After they left I asked Maggie to dance again, ‘Strangers in the Night’ seemed to apropos for this evening. I hummed and sang the song a bit, a bad habit of mine that some people find annoying. Maggie seemed to only push her body harder against mine. Her hand went into my hair, my hand slid down her back and beneath her dress at her waist where I found only one slim band of material that ‘V’d’; she was wearing a thong. My cock must have jumped because Maggie looked up at me as we turned away from the dance floor and reached down between our bodies and caressed my cock through my pants. I thought I would die right there!