Life of Elliott…

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Diary Excerpts #9 & #10… Guest Post

Dear Diary

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9….It’s been 2 years since I began going to escorts.
There has been times when it’s been months in between visits so it sometimes feels like a fresh start when I return , making me almost as nervous as the first time. However after the past couple of times with Tiffany I had become much more relaxed ,so I was feeling confident that this was going to be the day I cum during intercourse.
Tiff was away! It was my fault for not booking her as she was on roster so I assumed she’d be there. So I had to go through the routine of meeting girls , hoping to find someone I feel comfortable with. My confidence was slipping away as the ladies came and went….but then Lessa popped her head in. She was thin , short and tiny but had boobs that looked huge on her small frame. She smiled and we chatted nicely untill she stopped and asked….”are you Howie?” When I said yes she explained…”Tiffany told me you might come today”.
Then as she left she added , “I hope I see you soon Howie”.
I probably would’ve picked her anyway because she was hot , friendly and had massive tits… , but being a friend of tiff was a bonus.
Once in the room Lessa took off her very high heals which dropped her height to under 5ft. She was tiny!
I had paid 30 extra for kissing which I loved because it made our time seem much more like girlfriend and boyfriend.
She seemed to enjoy me licking her tiny shaved vagina and was eager to suck me off. Tender kissing and her apparent eagerness to please me stiffened my cock as her small hands gripped my shaft firmly and rolled a condom on. As Lessa squatted down , sliding onto my cock , I supported her by her tits. Feeling 2 hard lumps of silicon in her greatly augmented boobs. They were the first fake boobs I’d held but I didn’t mind as they looked amazing and her nipples were still fantastic to suck. Anyway her small pussy was tight and I could feel it slide up and down my erection , getting me a bit too excited! I sat up , kissing her as she rode me. Then I swung my legs over the edge of the bed and stood up! She was so light I could support her using just my open hands holding her bum cheeks.
She had her arms over my shoulders but only for balance as I stood there using her body as a sort of masterbateing doll. My body stayed still as I slid her body up and down my cock. I layed her on the bed and kissed her as I finally came! My first time actually cumming inside anyone but my wife since before being married. I felt more relieved than guilty. I hope now that I’ve done it once that I won’t be so hung up about it. Lessa lay ontop of me naked , her head on my chest , looking up she smiled…”Tiff said you were a sweetie”

10…. I return only 2 weeks later. This time Tiffany is there which is okay but I must admit if she wasn’t there then choosing another girl would have been exciting too. Anyway it’s nice when Tiff arrives to lead me up to the room because she’s happy to see me and on the way she laughs as she tells me what Lessa had said about me. Apparently Lessa had assumed I was going to be shy about being naked and reserved in my lovemaking but she had told Tiff that she was very surprised. Tiff laughed at my embarrassment as she nudged me , telling me how lessa had described the way we fucked mid-air. It was exciting to think the two had been talking about me.
Tiff felt sorry for me and said , ” aww it’s okay….she also said you were a real sweetie”.
Over the past 2 weeks I had been watching lots of lesbian porn partly to learn better techniques of pussy licking. I figured who would know better what girls liked than another girl. As soon as possible I go down on Tiffany.
Going fast and slow , firm and soft , penertrateing and teasing. I watched Tiff moan and writhe around as the tip of my tongue flickered lightly over her clitorus. After a big sigh she suggested we get into the spa for a while. We had 45min so plenty of time.
By the time we got dry and jumped back into bed my cock was getting hard. A few sucks later then on goes the condom as Tiff quickly lowers herself onto my cock before it goes soft. We were both thrilled when I stayed hard and fucked her for ages before cumming in her.
We hugged and chatted before Tiffany commented how my licking skills had improved a lot! I assumed she was just trying to make me feel good but she stopped me and repeated firmly….”no howie… was reeealy good! .., in fact ummm…”. She sat up but looked a bit shy about what she was about to say… ” umm this is a bit naughty but ummm…..could I sit on your face again?”.
There was only a few minutes left so it would have been okay to finish but an escort wanted me to lick her for her own enjoyment!
I left there feeling fantastic , like a young hot stud! My confidence was higher than ever. Tiff had ground her mound on my open mouth as she held onto the bedhead and screamed.

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Meet Howie…  a 53 year old happily married man living in Queensland, Australia. Unfortunately for Howie, his wife is no longer interested in sex. But, Howie still is, and since he loves his wife, and would never be unfaithful, he seeks relief from sex workers. Howie is not a writer, just an ordinary family man who keeps a diary, well hidden I’m sure, here is a page or two.

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Masturbation Monday

Wicked Wednesday... a place to be wickedly sexy or sexily wicked 

One comment on “Diary Excerpts #9 & #10… Guest Post

  1. Marie Rebelle
    April 7, 2020

    Sounds like things were getting hotter for you, Howie!

    Rebel xox


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