Road to Re-Awakening

Tasting

I was enjoying going to work Monday, Wednesday and Friday. The initial idea of three days one week and two days the next never happened since I really liked being there again.  The employees that Jan and I hired seemed to like having me around again and the place seemed to have that old fun but serious mood.  The newer employees seemed to fit right in and there was a good atmosphere.  

"I think you found a younger clone of yourself when you found Sean.  I just wish he'd ditch that white shirt and tie. Nothing really changed when he took over and we knew that you needed time with Jan" Charlie told me.  He was one of the first people we'd hired a long time ago and never sugar coated anything so I knew he was being honest with me.  It was good to hear from another person that Sean was a good pick for the job.

It didn't take long to meet the newer employees and while most were worried I'd change everything when I came back, they heard from the old timers that I wasn't like that.  I went to the kitchen to refill my coffee mug one morning and a few people there were talking as usual.  At least after my first month back they kept talking and didn't immediately stop when I walked in. My ears perked up when I heard the words "cabernet" and "pinot" but I let them continue talking without saying anything.  One person said "Your expert is over there.  He can tell you about the various types of wine all afternoon", pointing at me.

A couple of the newer people were a little shy, but we did have a casual discussion.  Finally one asked "Are you going over to the wine tasting event tonight over at the store on fourth street?"

Chuckling, I told them I didn't know they had one.  A couple of the people said that they were going after work and one invited me along.  Both were a few years younger than me and neither looked like wine people.  Cheap beer or whiskey looked more to be their preferred libations.  Indeed both were new to the world of wine and were finding out which varietals they liked.  We planned on meeting at the wine store at six when the event started.  George got there first with Danny and I a few minutes later. 

The store looked a lot different than when I had been in it the last time and had gone from "repurposed old grocery store" to "wine boutique" in the intervening years.   We all paid our fee, got a glass, information sheet and a pencil.   Several serving tables were spread around and there were a lot of people tasting.   I didn't want to take control of our group, but suggested a few good ways to start sampling.  "Don't be afraid of dumping it in the bucket if you don't like it" I said.

We made it through each of the tables, sampling the whites before moving on to the reds.  Danny kept asking questions and I told him what I knew while George just soaked it all in.  At the first table on our red round I ran into a woman I'd known for years.  Ann was one of the quiet ones that got a lot more lively once she had a little alcohol in her.  It was never over the top, but very noticeable.  I preferred the alcohol enhanced version.  We gave each other a hug and started to talk as we tasted the next set of wines.  When we got to the next table, I noticed she was no longer wearing a wedding band.  

Eventually the topic came up since she was very "hands on" with the three of us.  "Oh, I got sick of Harold and his mistress" she said.  From what I knew of her husband, he didn't seem to be the cheating type.  In fact, it was hard to think of him being very sexual at all.

"Oh?  That surprises me" I replied, trying not to pry too much.

"Yes, he spent more time with that business than with me.  I finally gave up.  I'd rather be a divorcee than left at home, bored" Ann said, giving me a wink.  The four of us finished the last of the tables and both George and Danny said they had to get home.

"Thanks, Ben.  I appreciate you guiding us tonight.  Now I won't feel like an idiot when I go looking for wine.  You showed us some really good ones too" George said.   It was the most he'd talked all evening.

"I have a nice cab franc at home, if you'd like to stop over" Ann said as soon as George and Danny were gone.  

I laughed to myself, never thinking that Ann was ever interested in me, but replied "Sure, why not."  I followed her home and after a few minutes inside her house, a young guy came out of the hallway.  He stood there in a glittery thong, choker chain around his neck and a short leash.  I chuckled since the shocked look on his face told me he wasn't expecting anyone to come home with Ann, much less someone he knew.

"Hello, Theo" I said.  He looked a little different than the last time I saw him and that was skipping the lack of clothes.  His hair was longer, there was chin patch for facial hair and two large star tattoos on each side of his upper chest.  Ann came back into the living room with an uncorked bottle and two wine glasses.

"Oh, I thought you'd be out tonight.  I take it you know each other?" Ann said. 

I laughed and Theo nodded.  I'm sure he was trying to figure out how to go back in time and hide.  "Yes, he used to date my daughter.  He's quite the upgrade from Harold.  It looks like you have an interesting relationship" I said.

"Oh yes we do.  I found that I'm interested in younger men that like to serve me.  Theo knows his place and can be quite fun" Ann replied.  I could see that Theo was uncomfortable with us talking about him but I followed along with Ann's conversation.  She filled the wine glasses and set the bottle down on the table.  It was a good vintage from an outstanding vineyard but I doubted I'd get to appreciate it like it deserved.

Theo took his spot next to the sofa that Ann was sitting on, waiting for her next command.  We talked as we sipped the wine, catching up on each other's lives.  When the first glass was empty, she poured the second one and we kept talking.  Well, Ann and I kept talking.  Theo stayed silent and watched our every move.  Once she'd put the empty bottle down, Ann looked at Theo and then at the bottle.  He got up and took it into the kitchen.  This really wasn't a scene that did anything for me, I preferred my partners to be on equal footing.   Theo came back and knelt on his pillow awaiting his next duty.

We didn't finish our second glass before Ann looked at me and said "I heard you ended your seclusion by visiting your children.  I'm sure you were bored to tears since you and Jan used to be so active."

I chuckled, maybe a bit too long before I replied "It really wasn't the trip I expected.  I found enough things to keep me busy and I completed Lea and Dan's to-do list.  There was a lot of driving and my attempts at camping along the way were total failures.  My stay at Ron's was probably the busiest.  I wasn't quite prepared for six days of hiking above nine thousand feet.  And then there were the tattoo sessions..."  I wasn't going to talk about any of the sexual encounters I had along the way for fear that it might make it sound like I'd been screwing anyone I could find now that I was out in public again.

"It does sound like you kept busy, but that wasn't the type of activities that I meant.  We all need a little sex to keep everything working, right?" Ann said in something between a motherly and doctor's tone.   It did remind me that I needed to book an appointment with my doctor for a physical.

"I'm sure it all works fine" was my response.  It wasn't the one that Ann wanted according to the scowl on her face.  I added "But... if you were hoping to see some proof I might be able to oblige."  That got her smile back.  Moments later we were kissing and her hand was unbuttoning my shirt.  Once she'd opened my shirt, I returned the favor and it didn't take long before the two of us were naked.  

We had never had sex before since she was in her sexless, monogamous marriage with Harold.  Her kissing was more aggressive than I expected, but that probably came from her newly exposed Domme lifestyle.  I was able to get a few glimpses at Theo and he was watching us intently but not disturbed by the sight of us.  Ann seemed to relish having another man being intimate in front of Theo and I wondered if cuckolding was another of her new interests.  

Slowly, I moved down her body, finding out what turned her on.  I listened carefully as my tongue and lips explored her, getting moans most everywhere and a few places of dead silence.  The loudest moans came when I started to eat her out until she said "Oh god yes! Finally a man that knows how to eat my pussy!"

I spent several minutes giving her oral pleasure and while my cock was hard it could use a pair of lips to get it ready for the next step.  Once I'd worked my way back up her body, I put a little pressure on her shoulders and got nothing but resistance.  Another attempt got a "uh-uh" telling me she had no intention of going down on me.  I knew several women over the years that did not like giving oral sex, to men anyway.  To me, that was kind of a deal breaker.  I'd accept some lame oral sex over the refusal to even try.  

My thoughts briefly went over to Theo and how he deserved at least a little oral sex in his relationship.  Some quick thinking gave me an idea to salvage this sexual encounter.  I stood up, pulling Ann with me and I said "Theo.  Get over here and suck me."

It was an all or nothing gamble.  I could offend Ann by taking control of her sub or offend Theo by giving him a command without his Domme's approval.  It really wasn't a world I'd spent any time in and was an act of desperation.  He scurried over and with a little twist of my body, I gave him access while he was still pressed against Ann's leg.  His lips were soft and his tongue gentle, unlike Ann's.  She seemed to like having me get more assertive and she began to kiss harder and deeper.  If anything, me giving commands to her sub had actually gotten her more aroused.

Theo was no stranger to sucking dick and I wondered for a brief moment if he had started before or after dating my daughter.  After thirty seconds all of his hesitance was gone and he was fully into sucking me.  My cock was fully hard and he liked taking it all the way.  His throat was tight but he liked to squeeze it around my dick before going back to sliding up and down.   

The stimulation felt good and Ann did drop down my body to examine and then lick over my nips.  While she didn't appear to like my tongue on hers, she seemed fascinated by mine.  After a few more minutes, I wanted to move on.  My hand reached down and gave a little tug to Theo's head and he stood back.  The bulge in his thong was much bigger than before and I wondered which excited him more, sucking dick or pleasing his Domme.  

When I laid Ann back on the couch, Theo went back to his pillow.  He seemed to get more excited when I began to penetrate her, but his hands stayed behind his back and he didn't try to stroke himself.  Instead, he just watched me fuck her.  Ann was a willing and vocal partner.  Her days of lay back and take it were long gone.  When she wrapped her legs around my body, I laughed to myself at how a half hour earlier I was ready to give up and go home.

We tried a few different positions, all with her on her back.  Laying flat lengthwise on the couch led to her turned crosswise with me on my knees and her legs over my shoulders.  I tried to make sure Theo had a good view each time.  Both he and Ann seemed to like it better when I would plow harder so I backed off for a minute and then slowly built up speed.  The resulting climax was really good and got my whole body shaking.  Ann tightened the grip with her legs around me, holding me fully inside her.

She loosened her legs a minute later and we were both breathing heavy.  The grin on Theo's face vanished as soon as he saw me look at him, making me chuckle again.  I had no idea what their regular sexual encounters were like, but I was going to put my own twist on it.  "Theo.  Come here" I said.

He gave a quick glance to Ann and then crawled over.  By then I'd pulled out of her and presented my cock to him.  He let out a soft whimper and came closer, licking up the sides and bottom of my dick.  A louder whimper preceded him swallowing my cock down to the base.  His tongue and lips lapped over the shaft, cleaning it of my cum and her juices.  I only let him go for a couple minutes before I pulled him off.  A quick look at him and another back at her gave me an idea.  "Strip" I told him and "On the sofa back" I told her.  It was a nice modern sofa with a wide back that was almost perfect for sex.

I don't think Ann was used to taking directions, but she did as I asked.  Theo stood there naked with his manhood pointing straight out with a little sheen covering the head from the precum that had leaked while he watched me fuck her.  He was almost my size, maybe a little shorter and thinner.  I handed Ann the leash and with a little maneuvering he was sliding into her.  My hand was on his back, encouraging him to drill her.  I had no idea if this was the first time he'd entered her with another guy's load inside, but the look of ecstasy on his face told me he enjoyed it.

He plowed her, usually with long strokes but at varying speeds.  After several minutes, she pulled on the leash making it dig into his neck and bending him over.  His thrusts changed and he'd occasionally plant himself in deep. I moved behind him and watched his ass flex with each thrust.  He had a cute butt and with the thoughts of how well he sucked dick, I wondered how many times he'd been fucked.

My gambles that day had paid off so I decided to try one more.  When he planted himself the next time, I drooled a long string of spit just above his crack and let it run down.  A finger pushed it in and Theo grunted.  I let him resume drilling Ann with my finger going along for the ride and working the spit in deeper.  The next time he paused deep in her, I added a second finger.  Another grunt came out.  My body was hidden from Ann and I was pretty sure she had no idea what I was up to.

More spit got added and I was almost ready.  The whimper from earlier came back when my fingers pulled out, replaced with a surprised groan when he felt my stiff shaft ride along the crevice.  He kept plowing, though I'm sure he knew what was coming next.  A half dozen strokes later, I pushed in.  Theo froze and gasped and Ann asked "What?" 
 
All I could do was chuckle before I began to rock my hips.  Seconds later, Ann knew what was going on.  Theo was still buried in her, yet she could feel my thrusts.   I added a little more spit which let me drive all the way in.  The moans coming from Theo told me that this wasn't his first experience feeling a guy fuck him.  I did wonder if this was his first time being in the middle of two others.  He just stood there, not moving even after I was giving him full strokes.  I gave him a hard thrust, paused, pulled back and paused again.  

That told him it was his turn and he began to slowly plow back and forth, driving my cock into him and then his into Ann.  Indeed, he didn't appear to have much experience in this position.  The more he drove in and out, though, gave him confidence to go faster.  Theo would thrust in and out a half dozen times and then freeze.  He did that a few times and I realized he was getting too stimulated.  I figured one or two more cycles and he'd reach his limit and it turned out to be three.  It felt good to have him milk my cock, but I didn't really have much more than three of four shots to give him in the way of cum.  From the length of his orgasm, he was full.  

I let up on his shoulders and slowly pulled back.  A few drips of my cum ran down his legs and he stayed bent over Ann, panting.  I'm sure some of it was from trying to refill his lungs after getting choked while Ann pulled on the leash, but also from his exertion.  When she finally let go of the leash, Theo backed away.  He looked over and gave me a brief grin.

"Theo.  Go clean up.  I don't want you dripping on the carpet" Ann commanded.  He quickly obeyed and disappeared down the hallway.  I reached down and pulled on my underwear and then continued by pulling my jeans back on.  While I doubt she'd give me the same orders, I didn't want to dirty the sofa either.  Ann slid back down on the sofa next to me and I sat down.  She had no qualms about staying naked and picked up her glass.

I picked up mine, too, but only swirled the wine around for a few moments.  It seemed like a waste to wash the taste of her out of my mouth with a really nice wine but in the end, I did.  

"I think he leans more towards guys than women, but he never fails to satisfy me" Ann said.

Looking back at her, I asked "Is that really a problem?  Unless he's neglecting you, I wouldn't think it matters."

"I guess.  I just don't want to get dumped for a guy" she replied.

"That seems to be a rather selfish reason.  Do you have any reason to think this is a life long relationship?  If not, then one of you is going to break it off.  Breakups can be hard but I really don't think it matters who their next partner is, unless maybe if it's Harold" I told her.  A few seconds later, I added "To be honest, Ann, I don't see him dumping you.  My guess is that you're going to use him until you're bored and then move on, so there's nothing for you to worry about."  Her comment had surprised me and I guessed that she wasn't as confident in her new role as she led others to believe.

We sipped our wines and continued to talk about what we'd been up to.  Theo came out of the hallway wearing a different thong but with the chain still around his neck and the leash dangling.  Ann gulped down the last of the wine in her glass and said "Give me a moment" before heading down the hall toward the bathroom.  

Instead of Theo kneeling on his pillow on the floor he came up to me looking worried.  "Please don't tell Lea about my relationship with Mistress Ann" he begged.

We were only a foot apart and I looked at him face to face.  "Theo, never apologize or be ashamed of what you like to do with a partner.  The only thing that matters is that both of you find pleasure in it.  Also, I never talk to anyone about my sexual encounters except for the people that were involved" I told him.  He seemed to be relieved but I also wanted to tell him one more thing.  

I grabbed the leash and pulled his head close.  "If Lea knew, I seriously doubt her impression of you would be any different.  Don't always think people will disapprove of your kinks and fuck 'em, if they do.  You're probably having a lot more fun than them, anyway" I told him quietly before Ann came back into the room.  Now, he had a grin on his face and I knew that my advice had given him a jolt of confidence.  I truly hoped that Lea wouldn't care and might get turned on if she knew, though I doubt she'd ever get Dan on a leash.

I had my shirt back on and glass empty when Ann came back and we said our goodbyes.  I got home to a very anxious dog and the three of us spent the next hour wandering the neighborhood in the dark.  We ran into only one other dog who was much more interested in meeting Walker than the cat on his back.  

I picked up the mail and found a small package that I wasn't expecting.  I opened it up in the kitchen and found four patches like Trevor, Greg and their motorcycle crew had, taped to a sheet of paper that said "Honorary Member" on it.  I had to laugh but it meant a lot.  I just hoped I could find a group like them to ride with closer to home.  There was a note from Trevor, too.  It said: 

"Ben, We enjoyed your visit.  Come back any time.  Maybe ride your Italian Stallion down, LOL.  BTW, now out to family besides my uncle.  Went way better than I thought.  Hugs, Trevor & Greg"   

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Author's note:  I'll be taking a break for the holidays and trying to decide whether to continue this story or to move on to another one.  Thanks for reading!