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It had been a couple of years since Ted had changed our lives. Dee became inspired to make some life changes including improving her health. She joined a gym and began working out 5 times a week. She started losing weight. She was now down to 140 lbs. Not bad for a former BBW that weighed almost 250 in her 30's after three kids. Her wardrobe began changing. Her clothes started to be more revealing. She seemed inspired to improve her life. And it wasn't just her body that started changing but her attitude as well. She was becoming more self confidant and proud of her changing body. We enjoyed spending time together and went out more often. Dee was starting to get admiring glances from older men and disparaging ones from their wives
. Our sex life improved too. What once had been a once a month event had increased to at least 3 times a week. She was limiting our intercourse, as she now called it, to once or twice a month, but I had access to her body with my fingers, tongue and her toys.
She purchased a few butt plugs in different sizes. She was very particular about which ones. The smallest was a little over 4 inches long and about 1 inch around. The largest was 6 inches and almost 2 inches inches in circumference. At first she found the small one a little uncomfortable but she seemed driven to begin enjoying it. I was hopeful that one day I would be given access to her ass but she was quick to tell me it belonged to Ted and always would be his alone.
She suddenly seemed to be an expert on sex toys. Her toy collection now included a large black dildo that she named Theodore. She said it was an 11 " insertable, but it measured over 12 inches. I don't know how she figured she was going to get that in her small pussy. Maybe it was just for inspiration. Everybody needs a goal.
I asked why such a long name and she told me that Ted had a long penis so it seemed appropriate. She had a couple of smaller ones too but they all had one thing in common. They were all black as were the butt plugs.
About a month after we returned from our Colorado trip on which we met Ted, Dee started loosening up. She started using the butt plug when we were having sex. It seemed to intensify her orgasms. I enjoyed watching her respond to my eating her pussy, fingering her and using one of the dildos on her. The bigger one was a little much for her initially but eventually she was able to take the whole thing and her orgasms were explosive. I wasn't allowed to fuck her most times for some reason, but she always allowed me to stroke and cum on her body. She still wouldn't let me cum in her mouth although she would suck me. Soon she started allowing me to cum on her nipples which she would then lift to her mouth, lap up and swallow. I found that strange but I was grateful for the new kink. It was still better than the old days in which we would fuck about once a month. She soon started keeping the medium butt plug inserted most of the day although she did remove it during her workouts at the gym.
She still enjoyed it when I used the nipple clamps. I would tug hard on the chains and insert a dildo in her hairy pussy while licking her clit. Her orgasms were so hard as she thrashed her head and yelled out "Yes, lover, fuck my pussy. I love it when you go so deep." I so enjoyed watching her cum and the added visual of the butt plug was hot.
Then one night just short of 2 years from our Colorado trip, I received a call from Ted while we were dining with friends. We hadn't spoken since the morning we parted at the hot springs. I excused myself from the table and went to the lobby of the restaurant to talk. I was surprised but we chatted a bit. He was doing fine, his business prospering but he noted that we were coming up on the two year anniversary of that magical night in Colorado. He suggested we might want to celebrate it together.
I was curious how that could happen but I was interested. I asked him what he had in mind. He knew that we lived on the Olympic Penninsula in Washington and he had a business trip scheduled for Seattle soon. He would pop for the suite since we paid for the room last time and we could join him for a long weekend. He knew of some fine restaurants in Seattle and he would cover the cost of the whole thing. Sounded good but I told him I'd have to check with Dee. He said yeah sure but his tone suggested he already knew the answer.
After Dee and I returned home from dinner I shared the details of Ted's call. She acted surprised but after being married to her over 35 years, I could tell she wasn't being honest and I felt she might have already known.
I asked her if she'd been in contact with him and after initially denying it she came clean. He had contacted her about 2 weeks after our return from our meet with him.
She said he called her as a friend who wanted to help her get healthier. He had suggested the gym and the lifestyle changes that she needed to make. When she went shopping for outfits, she would text him pictures of her in her new outfits and he would give it a thumbs up or a thumbs down.
He suggested the toys to get and encouraged her to buy the butt plugs he suggested.
He even asked her to send him nude pictures of herself so he could see the progress being made from her workouts.
I didn't ask her but I am sure he also monitored our sex life and what access to her body I was allowed.
She said she resisted the butt plug initially but that he insisted and told her that she would one day thank him for it. He also sent Theodore to her.
When I suggested that maybe meeting him again wasn't such a good idea She got angry and came back with the point that because of Ted our sex life and improved and I had to agree. So it was set then. I would call him tomorrow and set it up.
She was beyond happy, giddy even. We had the best intercourse we'd had since our return and she even orgasmed on my cock for the first time in over 2 years as I tugged on the nipple clamp chain stretching her breasts high in the air as I emptied my balls into her now roomy pussy. It felt like fucking as opposed to intercourse.
I called Ted the next day and told him the good news. He congratulated me for convincing her. I chuckled.
Ted had reserved a suite with an adjoining room in Seattle for a coming weekend in mid July for three nights : Friday, Saturday and Sunday nights. He needed to be back in Chicago for an early business meeting on that Tuesday.
Dee and I made arrangements to have our friends, Stan and Diedre, keep an eye on our place in Sequim while we were away. We told them that we were meeting an old friend for an anniversary celebration.
As the weekend approached we both became so sexually excited. The night before we left, Dee came to me and asked me to trim and shave her pussy. It brought back memories from almost 30 years ago when I had unwittingly shaved her for her boss's pleasure ( see It's Never Too Late 1 for the story). Dee prefers her pussy unshaved but I'm sure Ted had a different point of view. It did clear up that this wasn't going to be just a dining and drinking event, if there was really ever any doubt.
Sex that night was fairly hot but I didn't have intercourse privileges. I did use both Theodore and the large plug and she orgasmed rather quickly. Her nipples were off limits as she didn't want to start the weekend with sore nips. She did allow me to jerk off on a small towel on her belly.
The next day we set out for Seattle. Dee was dressed in a very sexy low cut blouse that showed quite a bit of her cleavage. She wore a bra that lifted her breasts. She had on dark nylons and a fairly short skirt, ending about an inch above her knees. Her shoes were pumps rather than high heels.
We took the ferry from Bainbridge Island so we wouldn't have to fight as much traffic which is brutal in the Seattle area.
We arrived at the hotel mid afternoon. Ted had made arrangements at the desk for us to be sent up. The bellboy would bring up our luggage later.
As we got on the elevator our excitement level rose. Could this really be happening! As we reached the door of Ted's room, it opened and we were greeted by a smiling Ted.
Dee threw her arms around him and gave him a deep kiss and a warm embrace. He invited us in and he offered his hand which I shook.
He showed us around to his beautiful 2 room suite. The bed room was large with a King bed and a chair. The sitting room had a couch that made into a bed and 2 chairs. There was a large bathroom with a seperate tub and shower. He invited us to sit.
After a bit of small talk about our travels, Ted told us he had made reservations at the seafood restaurant onsite for 7:30. and tomorrow morning we would use room service.
About that time the door to the adjoing room opened and in stepped a tall black man. Ted introduced him as Max, his business associate that was staying next door.
Max looked to be in his mid forties and was a little taller than Ted. Dee looked shocked and I could tell that she didn't expect anyone other than Ted as did I.
Ted apologized for the oversight
but said he was involved in the business meeting they'd had earlier that week and they had one tomorrow too in the meeting room downstairs.
He seemed nice and was very friendly so both Dee and I relaxed.
After a bit of small talk, we all left for dinner. Ted mentioned that there was a gym downstairs that Dee could use and he'd arranged for her and I to get a couple's massage at the onsite spa while he and Max were tied up.
Dinner was wonderful but we might have had a little too much wine. We headed back to the room. Our luggage had arrived while we were gone.
Ted excused Max who returned to his room next door. Then Ted turned to Dee and asked her to turn around and show him how she looked.
Ted was amazed at the transformation in only 2 years. Then he asked her to remove her clothes so he could get a better look. She was happy to show off her new body to him so she gladly followed his instructions. He first asked her to remove her top and she did so. Her push up bra was rather thin so one could see her silver dollar sized areola and hard nipples.
Then Ted took out his phone and asked if he could take a few pictures. Dee blushed but answered yes and I nodded in approval. I took a seat in a chair to watch the big reveal.
Next Ted asked her to remove her skirt and she did. I was shocked to see she had a garter belt on but no panties so Ted could see her freshly shaved pussy as she stood there on display for his pleasure. He asked her to turn around and bend over and as she did he was glad to see the jeweled butt plug. She had apparently followed his instructions on what to wear. He had already taken 4 pictures of her including a closeup of her filled anus. Next he had her remove her bra. She looked so sexy and proud as she stood there in her garter belt, nylons and her pumps.
Ted walked up to her and and bent down and kissed her. Dee immediately relaxed and returned his kiss.
"I've missed you so much and I need to be
fucked"
Ted suggested we move to the bedroom. There was a chair in the bedroom that I sat in facing the corner of the bed. Ted gently pushed her back on the bed and tenderly kissed her. He cradled her left breast and raised it to his lips so he could suckle on her hardened nipple. Her hand held his head to her breast and urged him towards her right breast and sighed as his lips found her nipple and his right hand pulled on her left one.
He then moved down to her shaved pussy and kissed it.
"It's Beautiful" he said.
Ted slipped off her pumps, stripped off his clothes and walked to the head of the bed.
From my vantage point I saw her pussy, looking vulnerable without her sparse bush protecting her, but beautifully framed by her black stockings and garter belt.
Ted offered his cock to Dee and she began licking it from the base to the tip as it quickly hardened. She craddled his balls and then started putting them one by one into her mouth while stroking him. She worshipped his big cock for a few minutes.
" I need your cock inside me" she said.
He quickly moved and knelt between her legs. He moved the tip of his cock up and down her wet pussy, then shoved his cock deep inside in one motion. Her pussy was no longer resistant to his girth as it once was due to her frequent practice with Theodore. He then lifted her ankles to his shoulders. I had a clear view of his cock violently pounding her as her butt plug winked at me. It was a magnificent sight and I took my cock out and stroked in unison.
It wasn't long before I heard Dee screaming " Oh, Ted. Fuck me. Fuck meeeeeee. I'm cumming!". He kept pumping her. She came again and still he kept on pounding her pussy.
I moved a little so I could watch her breasts jump each time his balls slapped against her butt plug.
Finally about ten minutes later, He started grunting and Dee screamed out
"Give it to me Ted, I want your hot cum."
I watched in awe as his balls twitched and he emptied inside her while I orgasmed at the same time.
He kissed her tenderly and told her that he had a special surprise planned for her tomorrow. Then he got up and motioned for me to clean her up. I actually enjoyed licking his cum from her pussy and then kissing her so she could taste their juices.
After I was done I laid down on the couch in the other room. Dee was in the bed with Ted and I could faintly hear them talking.
I wonder what tomorrow's surprise is.
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