Serving My Sister III A Virgin s Cherry
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Mary came into my life at a time when I was as down as a man could get. My wife had left me three months before for a new job that was three states away. She said she wanted to make a fresh start on her own and served me with divorce papers. Problem is she didn’t exactly start on her own, she took our three sons with her. Although I talk to them on my cell phone every night and we fly them in on one weekend a month, there is still a huge emptiness in my life and heart created by their absence. The next thing that happened was losing my job when the company that I had worked for, for so long was bought out by an out of state conglomerate. They just wanted the equipment and not the employees. We were given a very generous settlement that I used to start my own dry coating business in my garage. Being self employed had always been a dream of mine. Coupled with losing my wife and sons I felt no real excitement born from this new opportunity.
That is enough about my woes though because it was about this time that my life was about to take an upwards turn finally. I met Mary because I had secured a contract with a company whose name I won’t mention here that makes tarpaulin kits for open topped semi trailers. They have to have the cross members coated to stop rust and to protect the tarp. They loved the trial run I did for them and my prices were the best they had seen as I am a one man operation with little overhead. All they required of me was that I get business insurance which I probably should have had anyway.
I called my local insurance agent up and explained what I wanted and he told me he handled non-commercial insurance only. He gave me the name of an agent that he traded referrals with and then tried to talk me into upgrading my home insurance package as well. I declined and made my call to my new prospective agent. Her name was Mary Hasslebeck and damn did she sound sexy on the phone. That thought surprised me a little as I had not thought about women after my ex-wife had dropped her bombshell on me. We set up a meeting for the next day and said our goodbyes on the phone. I must admit I wondered about the lady on the phone a few times during that day and I knew she was probably married with children.
The next day arrived and I went to her office to meet her and from the point I walked into her office it was like a fairy tale which I might add I do not believe in. She stood up to greet me and I to this day still think she is the most stunning woman I have ever seen with my own two eyes. She was about 5’9′ tall which is two inches taller than me and she had medium length auburn hair with a touch of natural curl in it. She was dressed both professionally and conservatively in business skirt which was calf length. She had on a red blouse which is now my new favorite color. It buttoned up the front and although it fit loosely it could not hide the fullness of her breast.
She has since admitted to me that she felt the same way about me at first sight also. I am no Romeo and consider myself average but I am in pretty good shape for a guy of thirty-six years old. I spent four years in the Marines right out of high school and have always kept up a pretty consistent workout regimen. It has been even more vigorous than normal the last few months so I could exhaust myself each evening to ensure a good nights sleep. The first couple of weeks after my ex left me I turned to alcohol but quickly realized what I was doing and stopped immediately. I am 5’7′ tall and weight right at 185 pounds. I have closely cropped light brown hair with a touch of grey coming in at the sides now.
For the first fifteen minutes there was an awkwardness between us that we later understood was caused by our strong mutual attraction to each other. By the time we got out of that stage the insurance part of it was covered and the conversation turned personal. Making sure I didn’t sound like I was feeling sorry for myself I told her about my ex-wife and what she had done. I told her that every night I still talked to my sons, sometimes for an hour or more. We missed each other an amazing amount.
I found out that she had been divorced for two years now and she had been through a pretty bad marriage. He had been abusive but she was felt it had been worth it because she had two sons herself. Both lived with her and they were the same ages as my two youngest sons, 7 and 5 years old. She had casually dated a little in just the last six months but never had more than two dates with any of them. Only three different men total, all of which had been set up by her best friend Connie.
‘She meant well’ Mary explained to me ‘but she also finally understands that I will date when I am ready’.
‘I know what you mean, my brother had been trying to get me to go out since my ex boarded the plane’ I said laughing at the comment as I made it. I was happy when she laughed with me and I fell in love with her laugh from the start. ‘You have a great laugh’ I said, sorry as soon as I had said it because it sounded stupid to me.
She stopped smiling and looked at me seriously and said ‘Thank you, It sounds cliche but even something that simple is refreshing from a man. I have never asked a man out before but would you like to have dinner with me tonight or sometime this weekend?’ she asked me and looked hopeful and worried as soon as she said it.
I wasted no time at all in responding ‘I would be delighted’ I said. ‘I was getting ready to ask you the same thing’ I informed her. Once again we laughed easily together.
We talked for a few more minutes, mostly about my insurance papers that she would fax me tomorrow morning. Then we got down to business and selected a nice little Italian restaurant to eat at that night. I offered to pick her up but she said she would drive. I understood completely, that way if I turned into some kind of jerk she was not stuck without a ride home that night. Also we decided it would be separate checks and once again I understood that to. Too many men expect something in return for the price of dinner. All I expected was some good conversation and a few laughs and told her as much. I seen her eyes light up and I think that I got a few brownie points for that comment.
After leaving her office I kind of blundered through the rest of the day and didn’t get much accomplished. I had not been this giddy about a date in my life. Not even senior prom night when I was dating a cheerleader that I had high hopes for that night. What a bust that had been, she spent more time with her friends than she had me that night.
I went through my closet three times trying to find the perfect outfit for that night. I didn’t want to look like a business man but I didn’t want to be to casual either. I finally settled on a pair of dark blue Dockers and a casual button down white shirt with some color in it. The shirt fit across my chest pretty well but not to the point of looking like I might pop a button. She had said she would make the reservations for seven that night and I asked her what kind of car she would be driving so I could find her in the parking lot and walk in with her. She liked that and told me she had a black Toyota Camry. I had told her I was in a Suzuki XL-7 which was a two tone, black and grey.
Finally the time arrived and after a long hot bath and shave I was ready to go. I didn’t want to get there to early and look desperate but I didn’t want to get there right on time either. I was afraid she would think I was in no hurry then. I decided that it was better to get there early than to risk being late though.
I arrived at twenty minutes till seven and she was already there. This pleased me as I pulled into the spot next to her. I smiled at her and got out of my SUV and walked to her door and opened it for her. She smiled broadly at me and stood up and gave me a light kiss on my lips. I could feel my entire body tingle at just that slight touch from her and had to fight to keep my mind from racing away with ot
her more wicked thoughts.
She stepped back and looked at me a gave a low whistle. I was slightly embarrassed which she found amusing and in my best (which is still very bad) John Wayne voice I said ‘Aww shucks ma’am, thank you. You look mighty fine yourself in that getup’. She was wearing black slacks which revealed that she had nicely shaped hips and as with earlier a button down blouse that was loose but still showed enough curve to let a man’s mind run free.
She rolled her eyes and laughing she said ‘O boy, come on and let’s get a seat at the bar while we wait for our table’. Then she hesitated for a split second and asked ‘Do you drink?’.
Dropping my bad John Wayne impression I said ‘Yes I do, not as much as when I was younger but I can handle a drink or two’ I finished while smiling with my eyes and looking at how hers sparkled. I was wondering what this ladies flaws could possibly be because so far she seemed perfect to me.
We were seated at the bar and she ordered a hurricane which had four alcohols in it and that made me comfortable with ordering my favorite, a Jack and Coke. The conversation was easy that night at the bar and over dinner. We talked about everything from our childhoods all the way to our work lives. We were both consumed with our sons and our lives took a backseat to their happiness. I was sorry to see dinner done and desserts eaten because I was not ready to depart from her presence.
We paid for our checks and left nice tips as the waiter had been perfect. He was always there when we needed him but he left us alone at the right times as well.
‘May I walk the lady to her car?’ I asked as I held up my arm for her to take.
She laid her arm upon mine and said ‘The lady would be honored to be escorted to her car by such a gentleman as yourself’.
This time there as no laughing because there was a sexual tension in the air that was as thick as a London fog. We had not spoken of sex at all that evening but we are both adults and know that it is a natural part of being attracted to someone.
We arrived at her car without a word spoken between us as I turned to her and put my hands on her waist, hoping I was not reading her wrong and being to forward. ‘I would love to see you some more and I hope you feel the same way’ I said as I leaned in to kiss her.
Catching me completely by surprise she reached up with both hands and grabbing my face in her hands kissed me hungrily and deeply. In no time our tongues were probing each others mouths and we were holding each other tightly as I felt my erection reach what was maybe a record size for me.
Pulling away she said ‘I have not made love to a man in over two years now. I want that to change tonight. How far is it to your place?’. She asked.
Having trouble getting my composure back I had to try twice to speak before the words would come out ‘Maybe fifteen minutes, it depends on how fast we drive.’ I answered.
‘Drive as fast as you want’ she said. ‘You will not be able to lose me’ she answered with a wicked smile on her lips and with that she got into her car.
I got into mine and after starting it I had to adjust my erection because it was becoming painful in the position it was in. I did speed on the way home although not at a reckless pace. We had the fortune of not catching a single light and made record time there.
I pulled into the driveway and she pulled up next to me and was out of her car before I was. She practically raced around to my door and as I got out we once again embraced in a kiss that was even more passionate and hotter than the previous one. We kissed all the way to my front door and even as I fumbled with my keys.
As I was unlocking the door she started rubbing my crotch and grabbing me through my pants. I had barely gotten us into the house and the door shut behind us when she grabbed me by the waistband of my pants and said ‘Bring it here, I have to have you in my mouth now’.
I could not believe my ears because my ex had hated sucking cock. She would only do it because she liked getting her pussy ate and I had stopped doing that in protest.
That thought passed through me in about a millionth on a second and was gone because by that time she was down on her knees on my foyer carpet right inside the door.
She had my belt undone and when I tried to help her unbutton my pants she slapped my hands away and said ‘Mine!’ while looking up at me with a wicked smile again.
What happened next I will try to explain. She got my pants open and reached in and pulled my cock out and smiled at it and said ‘Nice’. I am not a large man but like any man I have measured myself and am about seven inches long. My blessing is that it is thicker than the average cock and fills a woman up nicely. She looked it over for a second and then dove down onto it. I have never felt a hotter, tighter mouth than hers that night.
She started moving her head up and down on my cock and with each slurping noise that came out of her mouth as she sucked on me my excitement grew. She yanked my pants on down and without her missing a beat I stepped out of my shoes and my pants and underwear. She cupped my balls with one hand and the other one was working my cock with her mouth in perfect unison. It could not have been forty seconds before I started feeling that familiar pressure building up inside of me and I tried to step back and stop her.
‘No, I want to taste you’ she stopped sucking long enough to say and with that she went back to work. She was sucking my cock as furiously and hungrily as she had kissed me. Her pace quickened as she knew that I was growing closer.
So I did the only thing I could do at this point. I held her head gently in my hands and said ‘Damn’ in one long hiss as I allowed the flood gates to be opened and started cumming in her mouth. I knew the amount of cum that I was capable of producing and had not unloaded in months as I had been to depressed to even beat off and I expected her to pull back or at least start gagging on it.
She did neither, instead swallowing it all as fast as I could unload it. After what seemed like an hour I finished my orgasm but she continued to suck me dry. Not surprisingly I did not go limp but stayed hard in her mouth. It wasn’t even an option because it still felt so good. She sucked on me for another minute or so and then smiling stood up in front of me pulling my shirt off as she did so.
Standing completely naked in front of her I grabbed her face in my hands and kissed her deeply wanting to taste myself in her mouth. This seemed to increase her passion as she reached down and started rubbing on me again but it was my turn to slap her hand away with a wicked smile.
I took that hand and led her to the living room and by the couch in the center of it. Once again I turned her towards me and kissing her slower because I was wanting to set the tone now and she seemed willing to let me I started rubbing her breast through her blouse and bra. I unbuttoned her blouse as we kissed and reached around the back to unsnap it only to find no snaps there. Maintaining our kiss I pulled away a little and unsnapped her bra from the front and pulled the cups to the side allowing her heavy breast to fall into my chest.
I stepped back and slid her blouse and bra off of her shoulders and let them drop to the floor at our feet. I admired her large breast which were moving up and down at a steady pace because of her heavy breathing. There was virtually no sag in them and she had very large areola and nice dark nipples.
Stepping forward and kissing her once again I lowered her to the couch and kissed my way not so slowly down to her nipples. I took the left one in my fingers and started slowly rolling it around to check her response which was to arch her back up towards me. Then leaning down towards her right one I sucked it into my mouth and immediately felt her hands on the back of my head pushing my face int
o her breast. I lightly raked my teeth across her nipple and with this she pushed my face hard into her breast and said ‘That’s it, suck my titty. I love to have my nipples sucked hard’.
That was all I needed to hear and I really went to town on her tits then. I reached down and started rubbing her crotch through her slacks with the heel of my hand. She greeted this by rubbing her crotch against my hand rapidly. I decided to not leave her waiting any longer and quickly undone her pants and slid them down and off her feet. Her panties went with them and it wasn’t until later that I found out she had been wearing a black thong under them.
With no shyness at all she parted her legs for to expose her swollen pussy. The lips were open and there was plenty of moisture all around. I got my first good whiff of her aroma and it almost drove me insane with lust. Now it was I that could wait no longer and I buried my face in her pussy making her cry out.
‘Yes’ she practically screamed, ‘eat my pussy good.’ she ordered me. Not being one to ignore orders from a sexy woman I tore into her pussy like I had no other before it. I stuck my tongue inside of her and she tasted better than any other woman I had ever had. I could not believe a woman could taste so damn good. I was licking and sucking up her juices as fast as her pussy could produce them. I was careful to avoid her clit so far though but as she neared an orgasm I took two fingers and stuck them inside of her with the finger tips curled upwards towards her ‘G’ spot and started sucking hard on her clit. This set off an orgasm or orgasm’s, I could not be sure which that would last for a full 30 seconds or more. Her pussy had gotten so tight around my fingers I could not move them in and out anymore but I still was able to curl and uncurl them against her ‘G’ spot.
Doing this to her had built my excitement to an even higher point than it was before my blowjob from her. I stood up and grabbing her hips rolled her around and placed her with her knees on the couch with her torso above it. I moved in behind her and rubbed the head of my cock up and down her slit to wet it and then moved it into her.
‘Yes’ she hissed through clenched teeth. ‘Fuck me hard that way. Make us both cum’ she pleaded.
With this being said I put my foot up on the couch by her knee and moved all the way into her and didn’t waste any time thrusting into her like a sex starved teenager. The sound of my hips slapping into her round ass is what finally put me over the edge and she was reaching down between her legs and massaging my balls each time they slapped into her begging for me to make her cum.
As I got close I laid my chest into her back and reached around her and put my forearm across one breast and grabbed the other one in my hand and was working it pretty good when we both came together letting out one long moan of pleasure and relief together.
We took a shower together and made love again much slower that night and the next morning she woke me up by straddling my cock and riding it until we both collapsed. The rest as they say is history.
That night was eight months ago. Everything has went well since then for each of us. I now have custody of my oldest son who is 13 now. It seems that in most states that after 12 years of age the courts listen heavily to what the children want and that is what he wanted. Me and Mary live together and the three boys all get along great full time in the house. My younger sons also get along great with hers as they are the same age and have many of the same interest. I have a larger garage being constructed now on my property because my business has more than doubled and I have 1 full time employee now. Mary’s brother Josh who is a great worker and gets paid well for it. I have no plans to outgrow my new building and with me and Josh working up to 14 hour days we can handle a full workload for that building which we are both willing to do. I plan on making him a part owner in the near future as well. He is earning it.
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