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Tim and Abbie 71: Brian’s matchmaking: Jessica  

Clairew1959 64F
95 posts
8/9/2021 5:17 pm
Tim and Abbie 71: Brian’s matchmaking: Jessica


Brian does not forget his promise to himself after the first dinner with Mark’s mother and sisters. Well, the girls, no, now definitely women at forty, deserve to meet men who will cherish and care for them. Their youth and young adulthood were totally ruined by the tyrant father they had.
It is bad enough what Mark has endured from him, but to see his sisters and Mark’s mother so repressed just chills Brian’s soul. Well, perhaps repressed is not the correct term for all of them, but held back from genuine relationships, for sure.
Brian sets himself on his campaign to change things. He keeps it to himself but is very inquisitive at the Wednesday dinners about the sisters’ interests and such. Brian is a very astute observer of others and incredibly good at gaining insight about them. It has helped him in his job and is helping him now.
So over the next few months, beginning at the start of October, Brian spends time on this special project while other things are going on.
Brian also learns that Mark’s mother is especially upset that Mark no longer accompanies her to church on Sunday, which he soon changes. Their pew is now filled not only with Jessica, Jennifer, and Patti but also Mark and Brian beside a beaming Patti each Sunday.
Mark isn’t thrilled with this getting up on Sunday but gives in to Brian’s pressure. Again, Mark is not sure why Brian is doing this. He squirms a bit, and his mother applies the same finger snap to Mark’s head as when he was young. Brian smirks, seeing this. A bit later, Brian does it to Mark when he again starts to be distracted during the service.
Mark glares at Brian, who only smiles at him and whispers, “Now I know how to keep you in line, young man.” Mark tries to look mad, but the thought that Brian is looking over him is so nice. He leans back and begins to enjoy the service and the message being given.
Surprisingly, it is a message of inclusiveness and acceptance. Mark reaches his hand to hold Brian’s, low in the seat, realizing the world is not all against them. There are those who understand and are expressing words that all are enfolding them in God’s arms.
From that moment, it is easy for Mark, and Brian, to join Patti, Jennifer, and Jessica on Sunday mornings, followed by brunch at a nearby restaurant, a tradition Brian has started.
Brian notices early on that one of the ushers, around Patti’s age, always makes a point of saying hello to her each Sunday and asking how her week has been.
About the third Sunday, Brian asks Patti about who the usher is. She replies, “That is George. His wife died about ten years ago. He is very active here since he retired. And is always so kind. When their father died,” Patti never used her late husband’s name, “George sent a beautiful plant which is still growing.”
Brian stores this information away for future use.
oOo
There is a man, just as shy as Jessica, who works in Brian’s bank’s mortgage department. He would be perfect for Jessica, who works for a realtor. Brian starts to talk more and more with the man, Roger, in passing. Not too much for Roger to think Brian is coming on to him. Though few at the bank think or know, that Brian is gay.
After a couple of chats, Brian takes the plunge. He asks Roger, “I was wondering, would you be interested in meeting a friend of mine? I just think that she and you have so much in common, you might hit it off. No pressure, but I just think the two of you might enjoy each other.”
Roger blushes deeply, “Oh, I...”
Before Roger gets too scared off, Brian breaks in, “We could go out all together for dinner. Me paying. Her brother, who is my partner, me, you, and Jessica. If you would like to?”
Now Roger blushes again, realizing Brian is gay, but not coming on to him, but offering him his partner’s sister. A bit strange, but then again, nice. He replies, “I think I would like that. But could you, beforehand, perhaps tell me more about her? So I am prepared a bit to meet her? To be truthful, I haven’t had that much experience.”
Brian smiles at him in such a caring way, Roger feels safe and secure. This might be a really good thing. Over the next week, the two have lunch together most days, and Brian tells Roger as much as he knows about Jessica and pumps up Roger’s self-confidence.
It is set for Friday night. Yes, Mark will have to miss a game night, but when he knows why he will comply. And he does. Wednesday at dinner, Brian presents the invitation to Jessica, who is surprised and overjoyed.
Friday night arrives, and after picking up Jessica, Brian and Mark drive to a very nice Italian restaurant about ten kilometers away. As they walk to the entrance, Roger joins them, and introductions are made in the parking lot.
Roger is a bit short at five feet seven inches, compared to Jessica’s five-ten. But he is very attractive with shining eyes and a twinkling smile when amused or enlightened, as he is with meeting Jessica.
At their table, Roger stammers some in conversation, as does Jessica. They are both a bit tongue-tied. But as the meal continues, and a couple of glasses of wine, a glow builds between the two. The conversation is now just between the two of them.
Mark tries to butt in a couple of times, but Brian puts his hand on Mark’s arm or leg to tell him to back off. Jessica and Roger are meshing. They are finding the perfect zones they have in common. First, working in the same area, moving to books and movies they like, and even philosophical beliefs and more.
Brian encourages Mark to lean back and watch a budding romance from the start. Mark catches on to what Brian has done tonight, At first, he is a bit peeved for not being told, but then realizes how sweet it is. And Jessica does seem so happy. Roger is interested, and more so, a nice man for his sister.
Mark hopes this works out to something. He looks at the couple, and then at Brian, and smiles. Yes, Brian does deserve a special reward tonight for sure.
When they leave the restaurant, Roger offers to drive Jessica home. He seems sober enough, and Brian urges him to do so. On their drive home, Brian assures Mark that Jessica is in good hands, and perhaps tonight will be fantastic for both her and Roger.
Mark is a little taken back at that statement, thinking about his sister in that way. But with Brian’s hand on his thigh moving up and down, and more up than down, yes, he hopes Jessica can finally enjoy such sensations also.
On Sunday, their pew expands by one more. Roger is sitting next to Jessica. Patti whispers to Brian that Jessica did not get home until Saturday morning. Then she was out Saturday afternoon until dinner when Roger joined them. “He is such a nice boy and so attentive to Jessica.” When Mark hears this, first he is annoyed, but calms and is happy for his sister by the time they all have brunch together.
One down, two to go, Brian thinks.
oOo
With the glow about Jessica now and Roger at dinner on Wednesday nights, not to mention more during the week, it is apparent that things are moving along quickly between the two.
Yes, the two started relatively chastely on Friday night, chatting on the drive home to Jessica’s house. They did have so much in common, starting with their shared field of work in real estate. Laughing over silly things they deal with on their jobs and with . From there the conversation moved to how they felt about political and social issues which they seemed to agree on also. Wondering why others can’t see the big picture at times
Books they had both read, and liked, or disliked, the same with movies, and ones that never did live up to the books they were based on. Time seems to fly by,
Realizing they have been sitting in front of Jessica’s house for hours, Roger takes the boldest move in his life. He leans over to Jessica and kisses her. Just sweetly on her lips, but both their responses make it something much more.
Looking deep into each other eyes, Roger drives away to somewhere more private, and for hours they kiss and caress each other. Both in their forties and still virgins, they do not take that step yet. But their endorphins are at high speed. It is sunrise by the time Roger does drive Jessica home.
Plans are made for the afternoon, which after more passion flying, ends with Roger at the house for dinner with Patti and Jennifer too. After Sunday at church and brunch, Roger is totally besotted by Jessica.
Monday afternoon, both skip away from work and are at Roger’s house. Agreeing to this plan, Roger has spent all afternoon Sunday cleaning it. They agreed to not wait any longer, they want to consummate their alliance.
Both are so nervous. Roger tells Jessica they don’t have to if she is not ready, with her assuring him she is. They sit first on his couch with glasses of wine. Roger kisses Jessica and tells her how he cannot believe how lucky he is to have her come into his life.
Roger confesses that he has never been with a woman before, just never met anyone like Jessica that he feels safe and drawn to. Jessica is touched by this and tells him she is the same.
They fumble a bit, removing each other’s clothes. Roger is in awe of Jessica’s larger, thirty-eight C breasts. He lowers his head and licks and sucks at them. Jessica holds his head as he does. It feels so wonderful to have someone adore her breasts like this. She has been embarrassed undressing, but she feels this different, vibrant feeling with Roger's reaction.
Not embarrassed about her body but realizing someone does admire it as it is. Suddenly, Jessica feels juices start to flow from her. Juices held back for years and years.
After time enjoying Jessica’s tits, which Roger will, again and again, the two undress entirely and make their way to the bed. They take their time exploring each other’s bodies for the first time. They have never had a chance to touch, feel, taste, smell, the other sex up close before, and this is their shared opportunity to do so.
It is a long, played-out afternoon. There is no rush. While both do want to experience the feeling of intercourse, both know if it does not happen today, it will happen soon between them. Instead, this is the time to discover each other. Finding what each other likes is such a fun way to spend a truant afternoon.
And Jessica and Roger do giggle over that a lot, both slipping away from work for this fun and games. Something they both, so straight-laced as they are, would never do, but ‘hee, hee,’ they have. Yes, it is late in life, but they are going to make the most of it now.
Monday afternoon goes on into the evening. They reach the point that both are so aroused and have explored so much. Jessica, on her back, her legs raised, her cunt dripping, ready to welcome Roger in for the first time.
Roger is between her legs, hard as a rock. His glans is running up and down her slit getting wet to press into her. And the moment arrives, Jessica moans as Roger breaks into her. It feels like her secret waterfall has been released at last.
Roger's cock head enters this inner sanctum for the first time moans with delight. Together they begin the ritual intercourse dance of couples throughout centuries. The patterned in and out thrusts making each feel themselves reaching higher and higher until they cannot go any higher.
Then at the pinnacle, both give in. Jessica grips her legs around Roger’s waist, holding him tight to her as she does with her arms. Roger pressing deep into her as he explodes, grabbing her around the neck and kissing her deeply.
This first time is fantastic. It is showing the love that neither is ready to express yet. But with this interaction, without words, they both know there is a deep love between them. No matter how long it takes, they will express this love to each other.
There are a few drops of blood mingled with their cum but neither care. Yes, there is that first-time pain for Jessica some, but the ecstasy outweighs it all. After all these years, Jessica can feel she is finally a woman entirely. And Roger is feeling much the same. To feel himself deep within a woman finally. And a woman that over so short a time he feels safe and secure with.
After, they fall asleep, holding each other tight. It is not until late evening Monday that Roger takes Jessica home. He is worried that Jessica’s mother will be upset, but Jessica calms him. By the family dinner on Wednesday with Brian and Mark, they are a confirmed couple.
Over the years, both Jessica and Roger yearning for someone, have read things so they know about different acts they can engage in. Some they think would be interesting, some they are not sure about.
The next several weeks, they use Brian as a sounding board to understand how to proceed. Several things are way outside of Brian’s wheelhouse, so he finally has to tell them to try to work them out on their own. Brian does wonder some about how far they are going at times.
In the end, by the close of the year, Jessica and Roger are a stable and secure couple.

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