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My Solution to Not Being Alone for the Holidays

Posted by: Age: 40's Posted on: 10 comments
13 likes 420 views Category: Sex Stories Couples Tags: Female-Male, Sex Stories Couples, Hand Job, Hollidays

As the holidays approached I realized I might be one of those people that for some reason I always felt sorry for when they would come to Christmas events alone.


This year it dawned on me that for the first time in a long time after a recent divorce I may be one of those people that attend Christmas functions alone, sure the kids would be around for Christmas the one event I was dreading was my office Christmas party and being an office supervisor skipping it was not an option.

So this all started a month ago when I was attending a Thanksgiving play at a local high school that a close friends daughter was in so I felt obligated to go, as I entered the front doors one of the few people I recognize when inside was a guy I only knew as Bill ,Bill was one of these guys that I'd best describe as a friend of a friend.

I'd see him around once or twice a year and about the only thing I knew about Bill was he had been divorced a long time and he was a local farmer and the few times I'd actually talked to him seemed a nice guy.

Our eyes make contact and I'm greeted with a smile and wave so I walk up and say hi mainly because I didn't know anyone else there and the way it looked he didn't either so we stood in front on the entrance to the auditorium and made small talk for a few minutes until we realized that the play was about to start and he suggested that since we're both there alone to sit together to which I agreed.

Throughout the play we continued our small talk and by intermission I'd realized I'd become comfortable sitting by him and even though Bill is far from my type I was actually glad he was there so I didn't have to sit through this thing alone. It was still during intermission that we were how dreadful it was going to holiday parties alone and jokingly I think he brought up that we could help each other out and attend each other’s functions, mine being my office party and he had a seed company that he was involved with that had an obligation to go to as well.

When he brought it up I laughed it off but as the play continued I started to give this some thought and by the end of the play I actually thought it was a decent idea and as we were getting up to leave I asked him if he was serious about the offer and we spent the next 15 minutes making plans.

I went home that night actually kidding with myself that I had a date with Bill and wondering if I should go through with it because as I had mentioned Bill was certainly not my kind of guy. For the most part he really wasn't a bad looking guy but every time I'd ever met him he had this 4 day beard thing going and this huge Sam Elliot mustache and I didn't care for facial hair do to describe him best he always appeared rough around the edges, and another thing was he was short. I've always been attracted to tall men and he was certainly not tall, maybe slightly taller than me, and lastly…I am a city girl and well he is certainly country.

Well, my office party was the first on the list and I still had second thoughts about backing out of this agreement but ended up deciding to go, our agreement was he meet me in the lobby at 8 pm and we enter together and introduce each other as just friends and we had also worked a few ground rules, first one being the we were not to leave each other’s sides and the other being we only stay 2 hours at each event.

So, Saturday night is here and I arrive and start laughing because I still had no idea what his last name was and I didn't even know what he drove so I didn't even know what to look for or if he was even going to show up when I catch sight of this huge shiny pickup pulling in and I again start laughing thinking I'll bet that's him and sure enough it was. I stood at the entrance as he walked in and was honestly shocked, he really cleaned up well, I mean clean shaven other than the mustache and well-dressed so as we approach the party I thank him for coming and tell him how nice he looked and he told me the same.

The 2 hours went off without a hitch and I finally tapped my watch and he smiles back and soon he walks me to my car, pats me on the back and says he'll see me next weekend...to be honest I was honestly a little disappointed he didn't at least ask me out for a drink or something so I drove home got undressed and masturbated as I watched some porn on the computer.

The following Saturday was his event and because it was further away (50 mile) he told me he'd pick me up other than drive 2 vehicles and that afternoon I caught myself spending a little more time getting ready including picking out some sexy undies and even did my favorite trim down there (racing stripe). He arrives on time in his huge shiny pickup and again well-groomed and soon on our way and before I knew it we were pulling into the hall and this time as we started getting out he says just a minute and actually came over to my side to help me out of his truck but in doing so and purely by accident in sliding down the seat caused my dress to hike up giving him a pretty good leg shot but to my surprise he looked away as I gathered myself and repositioned my dress.

The first thing I notice once we enter is that these seed corn people like to party, drinks were flowing and I actually had a great and Bill, even though he drank very little because of the drive was more than happy to keep my wine glass full.

As the night went on the band started to play and soon Bill whisper to me saying, "I know it’s not the deal but would you like to dance".

Because I've always liked to dance I quickly accepted and to my surprise again he wasn't a bad dancer either and like so many bands do they will go from a fast toon right into a slow dance kind of catching us both off guard but finally both rather awkwardly put our arms around each other and danced which was really more just swaying and talking and at times would brush against each other and that's when I got the shock of the night, GOOD OLD BILL HAD AN ERECTION! And even though I could tell he was trying to avoid it brushing me it was.
Well for one thing it’s been a long time since I've felt an erection against me while I danced with a man and I can honestly say I was a little flattered but for another thing because of his height and the fact that I wasn't thinking when I put on heels that night not only was it brushing against me but it was hitting me right between the legs...WOW!

We danced 3 dances and in all of them he was trying so hard to keep it from brushing me but I think it was me that kept causing it to do so but finally our 2 hours had come and gone and as agreed we said our goodbyes and started our drive home.

We were no sooner out of the drive when I told him that I had a good time and I enjoyed dancing and haven't danced with a man in a while (wine talking now) and he said he hadn't either and also had a good time and with a few moments of silence I said quietly, "Oh so that's why" "....Why what?" "..you know" "....no…what?" "..its ok Bill...don't be embarrassed I was kinda flattered...I mean dead silence...finally I say...sorry I didn't mean embarrass you...well If you must know girl...it was more your fault...mine ?..yes...the way you looked tonight, that dress…for the first time in my life all the guys there were envious of me. What a sweet thing to say...and with that I unhooked my seat belt and slid over in the seat next to him and said…watch your driving...and with that placed my hand between his legs and almost instantly he was hard again...rubbing it through his dress slacks just made it get longer and longer and I soon realized it had escaped his briefs and I'm not kidding was half way down to his knee.

Well now I just had to see it and with his help opened his belt, unsnapped and unzipped him and soon had it all in my hand. I continued to stroke it for the next 40 miles as we talked and even kissed it a few times until he finally said...umm...Anne...you had better stop that a bit...oh why...don't you like it?..ummm no I'm liking it too much...with that I took my hand away , kissed his cheek lifted my butt in the air and pulled off my panties and covered the tip of his cock and proceeded and that was all it took when I could feel his warm cum filling my panties.

All this was just in time to get things put away and pull in my drive way, without hesitation I tell him...well you owe me one and asked him to come in...he did...and boy did he repay me...
..................I'm gonna see him again this weekend...........




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