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Shyguy654 Member Since February 15, 2021

A surprise you will love I promise

Shyguy654 1405 days ago on Transgender Stories

I got to the hotel after a long day of travel and quickly unpacked and showered and washed the grime of travel off. I shaved my legs and slowly washed the curves of my body while sipping a nice Rose from room service and got dressed. I was looking to make tonight special so I put on my red satin and lace panties, matching red satin bra, red lace garter belt and black nylons the ones with the line running up the back as they highlight my calves when wearing my 4 inch heels. I carefully did my makeup and styled my slightly longer than shoulder length brunette hair into a wavy modern style and put on my red lipstick. I stopped and stared at myself in the mirror and thought that my 5’ 6” frame which was athletic and toned looked good and said, “Still got it at 38!”

I put on a Navy Sati

I needed it badly and got it good!

Shyguy654 1405 days ago on Sex Stories

Super Excited!

I woke up feeling super horny today. I knew that I had to find some sexual satisfaction so I rolled over and began paying with myself like I sometimes do. It worked for the time being but I still had that desire for sex.

I showered up, shaved up, trimmed up and put on a pair of blue and white polka dot panties and a matching skirt. Added to it a nice blue satin bra, white silk blouse, low heeled red pumps and white stockings held up with a white lace garter belt. I did my long brunette hair in a pony tail and take my time with my makeup. I head out the door. Not only feeling sexy but looking sexy as well!

It was late afternoon and I went to a restaurant where businessmen from out of town typically go and sat at the bar. I ordered a Palmetto and the rum tasted

Put it in me coach! I need it!

Shyguy654 1405 days ago on Cheating Stories

I picked the team knowing just a few names and since it was Little League, it really didn’t matter who was on it. But after the first practice, things changed in an instant. I am a happily married guy and have been faithful for 14 years of marriage and have a beautiful wife. But something about Danielle, Jordan’s mom, changed all that. From the moment we met, there was this energy, this excitement that filled us both. It is hard to describe but there was an instant connection and magnetism. Pure animal instinct.

I bumped into her one morning at a Starbucks and we exchanged pleasantries about the kids and what they were doing and how the team looked. We sat for an hour and I blew off two work meetings I had just to stay talking with her.

The season ended and nothing happened after o

Swing back and forth for fun and fantasy

Shyguy654 1405 days ago on Sex Stories

Kara and I were coworkers and had been with he same company for about the same time, just under 8 years. She was super bright and we collaborated on may projects together and we became very good friends. Her boyfriend and my girlfriend would often meet up for dinner and drinks and we were all pretty close. We were successful young professionals and were in general above average in the looks department.

One evening, Kara and I finished work and we went to the local bar and waited for our SO’s to come and meet us for dinner. The television had some daily talk show on and the topic was swinging, where couples swapped partners. Kara and I laughed at the topic and some of the responses and then she asked, “Have you guys ever thought about swinging?” And i said, “We talked about it once

Super Excited

Shyguy654 1405 days ago on Sex Stories

Super Excited!

I woke up feeling super horny today. I knew that I had to find some sexual satisfaction so I rolled over and began paying with myself like I sometimes do. It worked for the time being but I still had that desire for sex.

I showered up, shaved up, trimmed up and put on a pair of blue and white polka dot panties and a matching skirt. Added to it a nice blue satin bra, white silk blouse, low heeled red pumps and white stockings held up with a white lace garter belt. I did my long brunette hair in a pony tail and take my time with my makeup. I head out the door. Not only feeling sexy but looking sexy as well!

It was late afternoon and I went to a restaurant where businessmen from out of town typically go and sat at the bar. I ordered a Palmetto and the rum tasted

Best Hike

Shyguy654 1405 days ago on Gay Stories

Best Mates

I was backpacking the Appalachian Trail with my best friend Jack one summer. We started in Georgia and were on the trails for a few months. We have been friends since 3rd grade and have been through everything together: girlfriends, break ups, graduations, parties, deaths, you name it and we experienced it together.

One night after we settled into camp, we hit a nearby river and stripped down to cool off and clean the sweat and grit of the trails off of us. We ate dinner and we were sipping a little whisky and decided to drop some acid. We had done acid together a few times so we were kinda used to it. The cool evening felt good after a long day of hiking. We laid back and stared at the magnificent sky above and watched dusk turn to night, the stars beaming and waited

Rubies and love

Shyguy654 1405 days ago on Sex Stories

Rubies and Diamonds

My flight was delayed from Milwaukee to Boston and so I did what all business traveler do on a delay, head for the bar! I sat down and ordered a tall Stella Artois and the first taste was so refreshing, I almost killed it in one gulp. The woman sitting next to me said, “Thirsty, huh?” And I said, “Long day of travel and work, I feel like I earned it.” She laughed and said, “I hear ya. Long day.” And I replied, “Cheers” and we both took another sip.

Melissa was from Andover and was returning from a Pharma Trade Show in Minneapolis. She was a good conversationalist and we shared stories of our latest travels. Mine was from Seattle where I attended a conference for investment banking and my flight began with a 2 hour fog delay, then a tarmac delay, and when I

Jeans Shopping is fun

Shyguy654 1405 days ago on Sex Stories

Found the right size...

I am not a big fan of shopping for anything. I hate online shopping just as much as brick and mortar but every now and then, I require new clothes and a trip to the mall is necessary. I often loathe this experience but something happened this time that made me rethink when and how I shop in the future.

I went to the mall at around 9:30pm knowing it closed at 10 and figured it would not be as crowded as it would be during the day. I went to my jeans store, rhymes with Ducky Jeans, and began looking around.

The sales lady was late 20’s, cute and said, “Hi, I’m Jenna, need help finding anything?” In a typical bubbly and slightly flirtatious manner, like most sales people do. I said, “Just looking right now but I will probably need a dressing room in a b

Preston works overtime

Shyguy654 1405 days ago on Gay Stories

Secret Surprise

I go to work each day in a suit and tie and do my job to the best of its ability. It’s a mundane job and I get very little pleasure form my work. I do enjoy the office environment and there is this one guy, Preston, that catches my eye each day. He is a Senior Trader, like me, and dresses to the nine’s: custom suits, tailored shirts, powerful ties and polished shoes. We are pretty good friends and have known each other since he started 8 months ago.

We will sometimes head out for drinks after work and talk shop and that leads us to our personal lives. I enjoy our conversations and especially when we get to have drinks together.

After a Friday at work, we decided to head over the Sapphire, a new bar in the South End of town and drink our stress away. I orde

Alone time is fun alone again

Shyguy654 1405 days ago on Masturbation Stories

Alone again!

The art of self love is a great one! Nothing is better than masturbating without a time constraint. You can take you time, speed up or slow down, finish and do it again or get to a heightened state and stop and resume later. I find each has its joys and all are fun ways to spend time with yourself. The quick release is okay as it saves on time but the time consuming masturbation session is the best. For me, I do this:

First, make sure the doors are locked and you know you have unlimited time, meaning your SO may be out of town for the day or at least a few hours. After this, I get down to self love and take my time doing it.

I am a male and in decent shape. I run 6 miles a day and to various workouts to stay fit and toned. My body is not overly muscular but it