Hookup, Find Sex or Meet Someone Hot Now

Tim and Abbie 73: Brian’s matchmaking: Jennifer  

Clairew1959 62F  
92 posts
9/18/2021 2:12 pm
Tim and Abbie 73: Brian’s matchmaking: Jennifer


Patti and George's announcement comes at the start of November. Two of the three women are in happy and stable relationships now. But there remains Jennifer.
Jennifer is a quandary for Brian. At forty-two, she is close to his own age and has lived a rather sexual life. Since her teens, Jennifer mastered the ability to unostentatious at home. When needed, she could change that appearance with a bit of makeup, flipping up her skirt and opening her blouse to capture males' attention.
And even a couple of females along the way. All in rebellion of her neanderthal father. He was so brainless he never caught on even when she was all night and snuck in dawn through the garden door. Things that Patti and Jessica didn’t know but did perhaps wondered about. But never ask.
Jessica knew somewhat and covered for her at times, though Jennifer never asked her. It was like Jennifer wanted to get caught when she was in her late teens and early twenties to see what would happen but never did get that satisfaction.
Their father never acknowledged her wildness, though at the time did begin harshly disciplining Mark, who was much , for things. Jennifer took it as a challenge to go further and further to see if he would catch her to punish. Perhaps, hoping to pull the punishment away from Mark. But the old man was blind to anything she did. None of it made much sense. But then again, their father never really much attention to Jessica or her. Mark was the golden their father expected so much from.
So over the years, Jennifer went her own way having her own fun. Her paycheck was enough to put in her portion to the house upkeep while putting more than half into an for herself. Her parents, well father, did not need to know how well she was . And she did make sure there was enough to for things, and mom and Jessica were well provided for.
After her father died, Jennifer was able to have more fun away. She would be home most Wednesday nights for dinner and on weekends, though after with friends in the evenings. But now, the two nights a week of town on business was three, and late home from work more and more.
Patti and Jessica accepted as Jennifer always called to let them know. And both were happy that she was and about more than they were. And all in all, Jennifer was home enough, just the three of them, Jennifer sharing many funny stories to keep them laughing well after they finished tea sitting around the table.
Now Jennifer is in her forties, still with her looks and desires. She knows how she went about things never led to anything serious. She lacks that bond with someone who really cares about her as a person and not just someone to bang on occasion.
She is jealous when Brian introduced Jessica to Roger, and they it off so well. Then George and mom. 'Wow, their time in life to be so in love and even to the point of marrying. What changes will that bring?'
Jennifer tries to keep a positive attitude, but she finds herself sad and filled with self-pity more and more. Is there anyone there to love her? Or is she destined to be alone?
Brian has not forgotten Jennifer. All that has been happening in the last couple of months considering, it isn't that long. It is now the end of November. With Christmas on the horizon, Brian tries to think of someone who could be the perfect Christmas gift for Jennifer.
Even with her family not knowing about Jennifer's wild ways, Brian caught on rather quickly. Over the weeks, when he and she have chatted, she reveals more about that side of her life to him. Brian gleams that it is not so much her being used by men, but her walking away thinking nothing will happen, so why stick around to be hurt?
That part of her needs to change, or Jennifer will never get close to anyone.
On the last Saturday in November, Brian asks Jennifer to go shopping with him for a gift for Mark. It is a ruse. Brian has bought perfect Christmas gifts for Mark and all his family already. However, he wants to talk with Jennifer alone. So after a few small purchases, he edges them towards a pub for a drink.
Brian expresses his concerns to Jennifer and asks her what she is searching for that she feels unattainable. This outright question brings Jennifer to tears. Feeling a bit guilty for the asking, Brian is glad they are in a somewhat secluded booth.
Jennifer acknowledges that she has these traits and is unsure what she wants or why she acts this way with men. She admits that there was this one guy, years ago, who she was so attracted to. And to be honest, still is. Sexually it is nothing special, but intellectually they just click. Well, no, he, The Big Guy, as she calls him, always bests her but lets her know she holds her own in intelligence.
But he just comes and goes. For probably almost twenty years now. Not that he was with any other woman. Jennifer pretty much knows he hasn’t been, which is weird. But he can’t or won’t commit.
With tears flowing some, finally admitting to this now, Jennifer guesses that she keeps searching for someone like The Big Guy with whom she could engage intellectually and sexually. Someone interested in her enough to be around and not disappear. Someone who did want to make a commitment.
But, instead, she just hooks up with guys when she is feeling horny and wants them gone with the crack of dawn. Or she creeps away at that point. Never really giving them a chance even to display anything more than their dick action.
“Yes, Brian, I know, that is crude and horrible to admit. But what, minutes, if lucky, up in . Hey, okay, thanks. Felt good, and goodbye,” Jennifer said with a mix of humor and sadness. “And none are enough to make forget about The Big Guy.”
And then Jennifer confesses something even more, "Because Brian, The Big Guy has this radar about me. When I meet anyone close to that, at all, and I actually consider more than a couple of dates, The Big Guy shows up again. And of course, I will drop everything and run after The Big Guy again."
Brian realized he has a lot on his hands now with Jennifer. Does he take down his matchmaking shingle?
To back up just a bit.
Jennifer is a bit plump but in a very sexy way. She is just enough big-busted that they seem to be burst out always at you. She dresses business-like, with this sense of 'let's have fun.' More so than what Abbie does, but then in Jennifer's job, it is an asset.
Jennifer, out of secondary , with grades making her eligible for A-levels, rather than pursuing that (thanks to her father), found herself a job with a pharmaceutical company. She was hired as a salesperson, pushing their latest drugs to individual doctors at their offices and conventions.
She had just the right image the company was looking for. And the personality and social interest, shall we say, to make her a sterling employing.
Jennifer learned the information about each drug quickly and became a great asset to the company. Twenty years later, she is still a top employee each year.
Jennifer is on the road enough, with hotel rooms and expenses, to be able to play and leave. But, mom, and Dad, when he was alive, never caught on, just enjoyed the income she brought in, not realizing what all she did on her overnight trips or sales calls.
Jennifer sells well over her goals for the year to please the company. It works so well. But lately, she feels empty more and more as the years go by. Now here, in a pub, with her brother's lover, in her early forties, she is depending on him to be her fairy godmother like he has for her mother and sister.
Show his magic, wave his matchmaking wand and find her someone to really love and care for her too.
All she can think of is, ‘Jennifer, where has your life gone?’
Brian can see the pain in Jennifer's eyes and takes her hand, "I know how you feel. It was not quite the same, but I wasted years on someone who was not worth it in the end. And now, what seems like half a lifetime later, I have found your brother, silly as he is. But, all things considered, if I hadn't looked a bit deeper with him, I would not have realized how wonderful he is.
"Jennifer, maybe it is time you start doing that. First, cast off that old thing. Was it, is it, really love? What do you get in return? Then, please open your eyes to others offering themselves around you. Look deeper, and maybe you will be surprised.
"You are so smart, and yes, someone that can equal you that way. But there are many there like that. And if, as you say, The Big Guy is mediocre in that department, I am sure we can find someone much better in that field and still be intelligent," Brian finishes with a wicked grin.
Suddenly, Brian hears a shout out to him, and it is like a combination of wonderment colliding. His matchmaker sign has fallen to hang on one shingle is back stable again; Santa has just delivered the best Christmas gift possible; the angels on have sent down manta from heaven.
It is like a miracle is appearing before them. Someone that Brian would never have thought of, but oh, yes, so perfect. The exact answer for Jennifer.
Henry walks up to Brian, seeing him sitting in the booth and waving at Brian as he comes.
Henry, a bit of a doofus. But also, someone who has so much going for him when you deeply him. A physician's assistant, standing over feet tall with ruffled brown hair and eyes and firmly built. Henry is a walking encyclopedia of knowledge. But not in a show-offy way. Just able to quietly answer any trivia or passing question with ease.
Brian just shakes his head to himself. But, when needed, prayers are answered, even before requested times. Brian has known Henry since his college days. They see each other from time to time, but their paths do not cross that often with their different careers.
Henry is still single, Brian knows. Mainly from working so much; and from his rather shy manner. While good-looking, it is hidden a bit. Brian laughs to himself. Henry is much like how Tim was before Abbie. Another diamond in the rough. Needing the right woman to see his worth to help him shine.
As he approaches, Brian says quickly to Jennifer, "This is hard to believe, but I think this is your chance just walking up. Be open, take a chance, look deep, see what is really there. And in the same way, let your own inner light shine fully. All it takes is spending the time to rub the vase to see how it can shine for you."
Jennifer looks at him a bit funny hearing this, but as this man approaches, she looks at him, not just at his outer appearance but what might be underneath. And she finds herself sliding back on her side of the booth as she is introduced to encourage him to sit down.
Bingo.
That is all it takes. Well that, and as the afternoon moves into evening, the three, well mostly the two, chatting on and on. Jennifer and Henry seem to find more and more they like about each other. Seeing the time, Brian calls Mark to join them for dinner. Then around , when Brian and Mark thought they would head , it is announced that the weekly trivia game is starting.
Jennifer and Henry beg them to stay to play, so Mark and Brian agree. While helping with a couple of answers, the new couple is crushing it. And their team, well Henry and Jennifer, are the winners for the evening. The adrenaline of winning and the drinks help the winners ride of the pub in a happy daze.
Loving goodbyes are given to Mark and Brian as they fall into separate cabs for their journeys home or somewhere. Mark and Brian’s ride ends with a sedate evening at home. But for the other couple, it is not until Monday evening that they hear a report from Jennifer.
oOo
Jennifer is bubbling over with excitement when she stops by Brian and Mark's house after work that evening. She has not been home since Saturday. Jennifer is heading there now.
Henry is wonderful!
She and Henry talked about all sorts of things starting from the trivia contest. The ride in the cab had been a mix of chatting and more. Talking, they turned to each other. Henry a bit shy, but when Jennifer leaned towards him, they kissed with great passion. It felt like sparks were going off between them.
They had a hard time keep their hands to themselves until they got to Henry's apartment.
Especially since they had to redirect the cab driver from the first destination given to Jennifer's place. Outside her flat, they realized that things were moving to the point that perhaps that was not where they should be.
A new destination was given to Henry’s place, which surprises him and laughing Jennifer some.
But, at that moment, Henry suddenly is very determined.
Arriving at his flat, besides the increased , the driver was surprised with the relatively generous tip he received. of the cab, fumbling with paying the driver and the apartment keys, they managed to get in Henry's place before they started groping for each other's clothes. The kissing did not stop, except for pulling apart to make different observations. Everything was filled with lust, laughing, and spurts of conversation.
"Oh my God," Jennifer goes on with her rambling, "When he was undressed, I could not believe how well-endowed he was. It was massive. I could keep my hands or mouth off it." Then suddenly blushing deep red, Jennifer realizing who she is saying this to. Her brother and his lover!
They all laugh, and she goes on, just not quite so graphically.
"It was wonderful. We had such fun. Playing with each other. Henry brought me so many different ways to climax. Fingerplay, orally, and yes, with his instrument," Jennifer goes on, again blushing some.
Jennifer's floodgates about her hidden sexuality opened now can't be stopped, it seems. Especially since now, it is with someone she feels secure with, not just one-night stands or the hidden lover. Brian squeezes Mark's hand to help him cope with what he is hearing. They will talk about this more later to calm Mark.
"We never got out of bed until this morning when we realized we needed to get to work, which was a quick dash to get there on time. Now, I need to get home, so mom and Jessica don't think the black market has captured me. And I need to pick up a few things and then head back to Henry's for the evening," Jennifer gushes.
As she leaves, Jennifer<b> kisses </font></b>Brian on the cheek and says, "Well, bro-in-law or whatever, you did your magic again. not sure how you conjured Henry up, but not complaining. Oh, and The Big Guy did message me this afternoon – I told you about his radar – I have not replied."
Brian<b> kisses </font></b>Jennifer in return and whispers to her, "Don’t. Let this have a chance to work.”
Smiling them both, Jennifer leaves.
And as Brian shuts the door, he feels that the promise he made to himself has been completed. Now to comfort and explain to Mark about all the changes happening to the females in his life.

Jimbolover2321 50M  
10 posts
10/2/2021 7:45 pm

Interesting and quite intriguing, I will have to read everything up until this point of the story to truely understand the dynamics of the characters involved. Looks like I have an afternoon of binge reading in my future.


Become a member to create a blog