caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair was long and brown and she threw it around a lot. She was pretty and had a big friendly smile.
A few months after she started working I told her about the divorce my wife and I were about to get. I had to find a place to stay. She had been flirting since she started but I thought that's what she does, but no. She asked me if I would move in with her. She didn't know anyone and would love the company. So I agreed. I had been there a month or so on the couch and on the days I had off while she was at work I would dress up in my usual garter & stockings, 4 inch heels, waist cincher and a open cup bra. This had become my addiction the last few years as no sex was not going to get me down....I was going to do shit I only dreamed about...but what if I DID it. Carried out these crazy thoughts? I was into girdles at the time because of the super tight fit and I loved to make my thighs and belly bulge WAY out of my stockings and open bottom girdle. It felt so naughty! When I'd pull my legs up, my back garters would pull tightly, spreading my ass cheeks so sweetly, exposing my usually jones'n shaven asshole. I really love sticking just about anything in it and this day I kept thinking about borrowing her cucumber that was in the refrigerator and get her a new one after I had finished. In fact it was that veggie that got me started. I seen it and it was shaped bigger on one end than the other and had really big knobs or bumps all over the sides. I saw it and wanted it in my ass! But I was procrastinating because I didn't want to go to the store right after so I was watching girls with strap-on porn dressed up, clamps on my nipples, my heels on both sides of my head and as you can imagine, with my garters pulled inside my ass cheeks next to my asshole, when I pulled my legs up, they pulled my cheeks so tight it was a little painful but oh so naughty! My asshole had never been spread so wide and tightly so I was busy running my fingers lightly over it which made my 7" cut cock so hard and huge. I hadn't even touched my cock yet when the door was unlocked and there was Veronica, off early from work, mouth hanging open then laughing and comes running to me asking me not to stop and can she help or do I want her to leave? I said I'd love to have her help and she said she wanted to watch me finish what I was doing and said I could go in her bed and she would watch me. I was so excited. I'd always wanted to be watched by a woman or a group. On the way I got out the video camera and sat it on the dresser. She seen it and said "oh can I film you!" she was all excited. How could I say no? She needed lots of guidance but she had a blast! I laid on my back and with her 2 feet from my cock and totally exposed asshole my cock was raging. She wanted it bad and finally asked if I'd fuck her sometime when we got all night. woah....o yeah! I said. Anytime! I was strokin and bangin my hand for a while and that fuckin cucumber popped into head. I know I'll need it, I'm going to have to ask her to get it for me. She said WHAT! That thing ain't gonna fit in there! I assured her it will fit but take a a little while. She bounced out got right back and handed me the big green veggie after she washed it. I smeared some oil on it and my hole and she started filming again. She was so excited! I had never had anything this big in me before so I went Very slowly with the big end first (so when I pull it out, my ass lips pull WAY out with it...a fantasy I was about to try)I got the end past the sphincter and let out a huge moan. It felt SO good! And I am such a slut! Veronica was freakin out. She kept moving from the end of the bed to the side getting great close ups and angles. She was doing great except for the few times she got mesmerized by the action and drifted away with the camera...didn't blame her! It took 10 minutes or so to get the veggie stuffed a good 10-12 inches inside me and I started to pull it out and told her to watch and not miss what I was doing. Her eyes got huge when she seen that huge veggie pulling my asshole a good 2 inches up the shaft and going back . In and out for a while while I was crying out in sexual bliss. I suddenly pulled it all the way out and she got an awesome gaping asshole shot. Another fantasy fulfilled! The camera died and she put it down and wanted to suck me till I cum and then she could watch the cuke too. I let her have at it and she kept me from cumming right away and realized this chick knows some moves. She sucked me for close to an hour without a break and I ended up slammin that cuke so deep it just about disappeared. It was about 14 inches long! I just realized that may be where she got the idea to stick her whole hand in my ass but that is going to be the next story! When I came it shot a couple of feet up and I said it had been a few years since I could do that and she said she'd help with that if I wanted her to and of course I agreed...very thankfully! Thanks for reading.
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Categories: HardcoreShemalesTaboo
Posted by happytayls
1 year ago    Views: 1,554
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1 month ago
I'd be "happy" too if I had a GF like Veronica
4 months ago
wow so fantastic and erotic wish I was there too
1 year ago
Looking forward to hearing about your next Happy story
1 year ago
like it very hot
1 year ago
No wonder you name is "happy!"
1 year ago
love the storie