I fucked my Dads best friend while helping him pack his deceased wife's belongings for Goodwill.
Jim waa his name he was 59 and his wife Susan passed away three years ago. He was suffering from depression and his Doctor suggested that he remove her belongings from the house and hire a contractor to put on a fresh code of paint and flooring.
He spent months trying to pack her belongings but could never fill a box. He told this to my parents and my Mother volunteered herself and I 19 to come out on a saturday and help.
That Saturday morning my Mom got called into work as she is an EMT. I decided to go ahead since I've known Jim my whole life.
We got to business immedately. Packed up several boxes worth of niknaks and keepsakes she had collected over the years.
However, things shifted once we had gotten to her closet. Susan was simular to my petite size. She had an impressive collection of dresses, blouses and lingerie with hosery and shoes. Her jewelry was just as impressive. Jim watched with a settle grin as I paid close inspection of Susans wardrobe. He asked if I wanted to try any on and I notted. I modeled on a few sundresses and Jim smiled watching me enjoying the outfits that have been locked away. In the back of the closet was her wedding dress with garter and stockings. He asked if I would want to try on as well. I agreed and slipped it on with the tiara.
I came out and asked him to fix the rear and then spun it around the room. I noticed Jim was quite erect. I asked if he wanted to dance and he agreed. I kept applying pressure against his bulge in several passings of the hips. Then we caught eyes and kissed.
I rubbed his bulge from outside his slacks and pulled his manhood out and stroked him while kissing. Then I dropped in a squatting position and begun sucking him off. I had just broken up with my first real relationship so this felt surreal. After several minutes of sucking and deep throating his girthy cock. He removed the wedding gown and reduced me to the vintage white garter, stockings and heels.
He kissed me again and told me he had a vasectomy and hadn't had sex in almost five years. I laid on the bed and he spread my thighs and he inserted himself and mounted me for almost twenty minutes before climaxing inside of me. There was so much cum. Literally was still oozing out of me several hours after.
There after, I earned Susans wardrobe and Jewelry. We had a discreet fling for several months following. Before I went off to college I set Jim up on a dating app and he started mingling with society once more.
As for the wedding dress, he had it dry cleaned and he gave it to my mother to pass on to me when I'm to settle down. She has no idea 😈
Posted Jun 23, 2025, 4:10 AM UTC