April 7, 2025 Monday I got to see a blog fan this evening! He wrote to me April 1 to say his business was bringing him to Boston again! I had not seen him since a wacky winter night in January 2019! We emailed back and forth all week figuring out the details.
BackgroundHe first wrote to me in January 2013 to tell me he adored my blog, and he travels in my area sometimes and asked to visit. We have seen each other three times when he was in town on business:
1) our first visit on a snowy night in December 2013!
2) Our second visit was in 2014 and we ended up on a bench in the cemetery!
3) Our last visit in 2019 was another snowy night
I had not heard from him since February 2022!
He always treats me like a celebrity so his visits are very special.
It was great to catch up on his news, share a delicious dinner, and have some sexy dessert at his hotel!
Challenges
He was staying near Fenway Park, Boston’s baseball stadium, and asked to have an early dinner close by. I warned him we’d have to wade into 45,000 baseball fans trying to get dinner and get to the game, but that didn’t phase him. I was stumped on where to eat, so I asked some friends on FB and they gave me 13 ideas! I offered 5 to him, and he picked the most expensive one!
My day
I wrote to him first thing to start the day with some good cheer!
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from: Sassy
to: BlogFan
date: Mon, Apr 7, 2025, 9:41 AM
subject: Re: Boston visit
It's Sassy Day! Hope this day flies by!
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I had a routine morning, prepping for the cleaners, going out for breakfast and grocery shopping so we were out of their way. I got home at 1:30 pm and checked for an email from my visitor - nothing.
2:15 pm I got out dressy clothes to wear. I heeded nature’s call.
2:45 pm I showered, moisturized, clipped my toenails, and got dressed up in my Savers top, navy blue massage bra and panties, leggings and blue silky jacket with black silky socks and serious shoes. My Glucose Sensor fell off! I decided to skip it for now.
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from: BlogFan
to: Sassy
date: Mon, Apr 7, 2025, 3:37 PM
subject: Re: Boston visit
At my hotel. Will meet you at 5:00 pm at the Blue Ribbon.
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I was so relieved to hear he made it to his hotel and still plans to see me at 5 pm!
I brushed my teeth, grabbed two of my vibrators - the blue CVS and purple bullet vibes - and stashed them in my purse, then grabbed my phone charger and some tropical TicTacs.
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from: Sassy
to: BlogFan
date: Mon, Apr 7, 2025, 3:45 PM
subject: Re: Boston visit
Yay! So relieved to hear it. See you soon!
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3:50 pm I put on my blue wool scarf and my dressy blue raincoat, and ordered a Lyft.
I went downstairs to wait for the ride share driver and chatted with the neighbors in the foyer.
Heading to Boston
4 pm After much hassle with the driver trying to find me, I got into a Lyft with Angelo who drove me into Kenmore Square in Boston in the rain. He dropped me off about a block from the restaurant. The traffic was much better than I had feared!
4:38 pm I went to the Blue Ribbon Brasserie, stood in the foyer and emailed the Blog Fan to let him know I made it.
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from: Sassy
to: BlogFan
date: Mon, Apr 7, 2025, 4:47 PM
subject: Re: Boston visit
I made it! Roll on down! Waiting in the entry.
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Meeting the Blog Fan
4:47 pm He appeared at the same moment!
We went to the host desk - she was on the phone talking to someone who lost their glasses. Eventually she seated us in a corner banquet on the right. I sat at a right angle to him so I could rub his knee. We were the only ones there - my guess that Red Sox fans would not be getting a fancy French dinner pre-game panned out! I took a photo of the dining room.
He was rocking the “Steve Jobs look” with a black turtleneck sweater and jeans.
Delightful dinner and catching up
We looked over the menu - he chose the Steak Frites (filet mignon) with fries, and a glass of Cabernet. I picked the paella. I asked if he wanted to share a starter and he said to pick one. I asked if he’d eat a couple of snails and he nodded, so I ordered the Escargot! They appeared first - he ate two and I ate four.
We asked for bread to sop up the garlic butter and the server brought warm sourdough rolls!
We had a great discussion - so good to catch up! He asked if I was still living in the city and I told him about my move in 2020 during COVID. He asked me if I was still seeing Jeremy and the Northerner? Yup. He asked if I was still prowling and I told him no - had not been with anyone new in 2.5 years. He asked if I miss the excitement of meeting new men and I said I don’t - it was starting to feel more and more dangerous. He nodded. He said he has not found anyone near him in a long while. He talked about how his job changed during COVID - some for the worse and some better. He asked about Philip - I said he is retired and doing well. It’s so fun to be with someone who reads my blog and knows about that Sassy part of my life!
He was fascinated by the throngs of baseball fans heading to the ballpark despite the rain, wind and fierce cold. He asked if I am a fan? I told him I keep an eye on it, and used to be really into it, but not so much these days. I told him I wanted to be an umpire when I was younger, but found out that wasn’t an option for a woman when it would have been time for me to start. I was a statistician for the men’s baseball and basketball teams in high school.
He admitted to being 70 years old - I thought he was younger than I am. He looks great! I asked if he was planning to retire and he said no. He had a bunch of projects and wanted to keep going until he couldn’t. He told me about his projects. I told him about mine. He told me about his travels and how much he enjoys Europe. He asked me where I went to college and shared his educational institutions. I asked if the Federal defunding going on would affect his work, and he said it remains to be seen, but he doesn’t think so, but it might be bad for others at his employer.
The server packed up my paella and asked if we wanted dessert - I said I’d like to look at the menu. She brought us each one. I asked if he’d share a creme brulee - he said he was full but I should indulge, so I did! It was the perfect finish - cool and creamy and light!
He paid the bill and I thanked him. He said it would be covered by his business. Wow. He went to the bathroom upstairs, and I snuck a look at the check -- $240! And I saw his real name on the credit card slip. I had thought I knew it from Googling details about his life years ago, but was relieved to know I was right.
He returned and I went upstairs to the bathroom in the Vansanity Hotel. He was reading his phone at the table when I returned but smiled up at me with such a sweet grin!
Walking to the hotel
6:46 pm We joined the crowd heading to the baseball game, and strolled around the corner in the drizzle to Brookline Ave, past the ballpark and to his hotel.
At the hotel in his room6:52 We went into his hotel - the Residence Inn, and went up to his room 503, and enjoyed ourselves.
I hung my raincoat in the closet, set down my purse on the desk, and sat on the couch to take off my shoes. He reclined seductively on the bed, looking very sexy and invited me to come cuddle with him.
Cuddling and kissingWe shared a lovely horizontal hug fully clothed. That was a little odd, but I enjoyed being close to him. He kissed me for a long time. He helped me take off my top and bra, then worshipped my breasts.
Oral for meHe took off my leggings and panties (so I was naked except for my black knee socks, while he was still completely dressed and wearing his glasses!) and kissed his way down my stomach then got between my legs and went after my slit with his tongue! He stuck one finger inside me. I moaned and writhed and he kept it up until I was soaring. He said I taste so good and he adores watching me enjoy what he is doing.
He asked if I would sit on his face. I thought he wanted me to kneel around his head but when I moved that way, he turned me around so I was on my knees with my ass in his face! He licked me that way for a couple of minutes, then moved me around to cuddle and kiss some more.
Fun with toys
He asked if I brought my toys? I jumped up and grabbed them out of my purse. I showed him my purple bullet vibe and the blue CVS bullet vibe. He picked the purple one. He asked how to turn it on and I showed him. It started buzzing. He asked where to put it and I answered, “On my clit.” He asked, “Where’s that?” Oh my… I told him at the top of my slit and he pressed there… I told him to angle it up and under and he did, and it felt so good! He moved it up and down and around and I could not stay still. My hips popped up to meet it. He moved it down and inside me and I went still… that is not so great for me. I told him I’m a clit gal and he returned to the top and pressed and I exploded! He stuck a finger inside me and then licked it. He kissed me and stuck his tongue in my mouth so I tasted our juices mingled together. So sexy!
CMNF
We cuddled together again - me naked and him clothed. So strange. I began to wonder what he was hiding. I don’t recall this behavior from our other meets.
We talked about photos - he asked if I let men take them. I told him Jeremy is the first person who asked to do it and he enjoys them. He asked if I send them to J? I told him I do, and he also tells me to send them to Philip! I told him I post some of them in my blog. He admitted he has not looked in a long time but would be doing so soon. I told him to look for the tag Sassy photos or Sassy video. He chuckled. I asked him if he would play and look at them. He said he has not done that in a long while. I was very surprised! He said he feels too busy and too old. Huh. He asked if my husband reads my blog and I told him he knows about it but is not interested in reading it. He asked if he knows what I am doing tonight? I answered that he knows vague details, but is not interested in knowing more. He shook his head. He said, “I wish,” and I replied, “I know.”
He talked about how he thinks women and men have different sex drives and women especially just get tired of sex at a certain age and stop thinking about it. I disagreed, saying I’ve seen a wide range in both my women and men friends.
Taking care of him
I asked if there was anything I could do for him? He asked if I would suck on him? I answered, “Of course!” He asked if I like that? “Oh yes.” He said most women don’t want to. I assured him I consider it a fun part of any encounter. He took off his jeans and briefs in record time. He said he had not been hard in a long time but I could try and it would feel good anyway. I told him not to let me hurt him - to say ouch or something. He said to keep my teeth out of it.
I kissed my way down his stomach and out to his hips, then sucked his completely flaccid cock down my throat and sucked hard. He moaned and said that felt so good! I licked the top and stroked his cock and kissed his balls. He moaned. I sucked and then blew on him… then sucked him again, pressing him in and pulling him out. He quivered and said he was going to cum and asked if that would be okay, and I said "Absolutely!" and then he shuddered and I tasted hot white cum! I licked it all off the tip. He said, “I came! You did it!” sounding very surprised.
I have had fun with men who were flaccid, but never someone who was flaccid but could still cum. Fascinating. I felt very accomplished! I know a lot of it is the forbidden nature of our interaction, but take some credit for my technique.
Kissing and cuddling some more
I went back up his body to kiss him and we shared a lovely tongue dance. He asked if I like his tongue in my mouth and assured him I do. He asked if I like to put my tongue in his mouth and I answered, “I certainly do!” He smiled. We kissed for a long time. These are questions I categorize as "no one else I've been with wants to" and enjoy bucking that trend!
He asked me to lean over him and let my breasts fall in his face - I did that, and he sucked and caressed them. I saw the bliss on his face and smiled. Mmm..
Taking a break and talking
I got up to heed nature’s call. I kissed him on the forehead as I left the bed. He got up and put on gym shorts. We talked about what I found easy and hard about retirement. I talked about the good aspects - setting my own schedule, and single tasking and getting to do things at less crowded times during the day.
It's pretty clear that he finds retirement frightening and not something he will willingly do. I tried to reassure him and point out activities he might enjoy while he's still healthy, instead of work.
We talked about traveling. He wants to go around the world. I told him I seem to be done traveling and my husband doesn’t enjoy it, so we stay home.
Under the covers
I pulled back the covers and got under them and he joined me. We kissed some more, then got talking about our health, and his wife and my husband’s health. He said he is in good shape. I said I am healthier than I’ve been in 30 years.
He started to dose, then asked me if I would stay the night, said he would love to hold me. I told him I could not… that I need my CPAP machine to sleep and breathe. He said he has heard of that. I asked if he needed to get up early and he said not really, but it had been a long day and he was fading.
Parting
I took the hint and got up to get dressed. I collected my toys and stashed them in my purse. I brushed my hair. He talked about various TV shows he watches to fall asleep most nights - mostly PBS mysteries. I named some of my favorites and he has seen them all! He said he often falls asleep halfway through, so he doesn’t know whodunit. Heh.
He got up and gave me another long hug and several kisses. He looked at my phone while I summoned a Lyft, and said it looked easier than he thought. He said he still uses cabs. He helped me put on my coat, then held the door for me. Such a gentleman!
He wished me well, said he is bad at keeping in touch. I winked at him, said I’m there whenever, grabbed my purse and the bag with my leftover paella, and headed out.
Heading home
10:05 pm I went outside to the corner to wait for the Lyft. I checked MLB.com to see if the baseball game was still going - nope. It’s done and the Sox lost. Hoping that means less traffic.
10:08 pm messaged Hubby to tell him I’m on my way. He replied with a thumbs up.
10:16 pm I took a Lyft home - the driver said he didn’t know much English and I told him that’s okay and didn’t pester him - I read FB, and Gmail and went back over the delectable meal and all the sexy fun I had tonight!
hot. Yes very sweaty.
