Abby's Big Surprise

My wife and kids were away for a couple of days and I had agreed to help her mother Abby clean out her attic. I ate a quick breakfast and drove over to Abby's house across town. It was a cool and rainy morning so I wasn't missing my usual Saturday morning round of golf.

Jenna's mom is a widow, not an unpleasant woman, but we don't always see eye to eye. I guess you could say we maintained a friendly toleration of each other. Her husband died a few years before Jenna and I met, so I never knew him. Abby is 54 years old and a shapely woman who dates infrequently. With a little makeup and a nice outfit she can be quite attractive. I have caught myself staring at her large breast and long legs from time to time.

I was surprised to find her dressed nicely and waiting for me. I was a little miffed when I realized that I would be cleaning out her attic by myself. She was going out for the day and informed me that she would be home in the late afernoon.

I climbed up the ladder into the attic and found that she had organized the boxes and marked the ones she wanted to have moved to the garage. She said that they were mostly old clothes and shoes that she was donating to Goodwill. There were only about a dozen boxes so I finished in a little more than an hour.

I have had a life long fetish for women's lingerie. I love to peek in the lingerie drawers and laundries of friends and family whenever I have a safe chance not to get caught. I have pilfered several panties, bras, girdles, and the like over the years. I love to put them on and masturbate. I always experience an intense orgasm when I cum in a pair of silky panties or tight girdle while wearing a bra.

I was pretty familiar with Abby's intimate underthings and have raided her laundry basket on more than one occasion. I started getting the urge so I went to her laundry room in hopes of finding some of her sexy underthings.

I hit the jackpot! Sitting on top of the basket was a sexy black lace longline bra, a matching open-bottom style girdle with garters, and even some sheer black hose. I giddily grabbed them up and ran up to Abby's bedroom so I could take advantage of her full length mirror.

I quickly peeled off my clothes and pulled on the girdle. I loved how my hardening cock felt encased in the tight stretchy fabric of the sexy undergarment. I then wrapped the bra around my torso and hooked the clasps. I twisted it on and slipped my arms through the straps. I was getting so excited that I was quite lightheaded as I peered at my sexy self in the mirror. I sat on the edge of her bed and slowly rolled on the stockings and attached the garters. I stood up and marveled at the image in the mirror. I felt so sexy.

Then a thought came to me. Perhaps in the boxes I had place in the garage I might find a dress or skirt to put on. I was pleasantly surprised to find several skirts and dresses that actually fit quite well. It dawned on me that these outfits were too large for Abby. I wondered where the had come from. I opened some of the other boxes and found several pairs of high heels that also fit my size 10 feet. This was too good to be true!

I decided to check all the boxes and then I hit the motherlode! One box was full of bras, girdles, slips, corsettes, hose, garter belts, and panties. I decided to keep that box, and after going through all of them, had managed to find three complete blouse and skirt outfits, four dresses, and even a lovely black evening gown.

I took a pair of black high heels and the gown and went up to Abby's room. I pulled on the gown and somehow managed to get the zipper all the way up. I put on the heels and began sashsaying about the bedroom. I then laid back on her bed and pulled the gown up over my thighs and began to stroke my rock hard cock.

I was just about to spray a hot load when I heard, "Oh my God! What are you doing!!!"

I opened my eyes and in utter terror saw Abby standing next to the bed. I was past the point of no return and came all over her stockings and girdle.

Time seemed to stand still. She ran from the room and I just laid on the bed spent, not knowing what to do next. I got up slowly and the gowns skirt fell around my ankles. I reached back to undo the zipper but couldn't get it to move. I was trapped and caught and there wasn't anything I could do about it. I thought about ripping the gown off but decided to face the music and asked Abby to help me.

I padded down the steps and found her in the den pouring herself a large vodka. "You know Tom, I am shocked to see you like this, but not completely surprised.", she said. "I see you found my late husbands things." "He liked to dress up as a woman and then make passionate love to me", she revealed. "He said it always made his orgasm much more intense and indeed he was a better lover when he was dressed". "Does Jenna know you like to wear women's things?" "N-N-N-ooo", I stammered.

I couldn't believe my ears when she said we could keep it our little secret, on one condition. "You will wear lingerie whenever you fuck me Tom, and I want you to fuck me right now!" She took me by the hand and led me to her bedroom. She unzipped my gown and I let it fall to floor. She removed her blouse and skirt and we climbed onto the bed.

I kissed her passionately and massaged her big tits, she flopped them out of her bra and I suckled on them and ran my hand over her wet panties. I pulled the crotch of her panties aside and licked her sweet pussy. Soon her panties were off, and before I knew it I was plowing my stiff cock into her hot wet pussy. I pumped deep and hard into her for quite some time and soon had her shaking in orgasmic pleasure. I thought about pulling out before I came but she held me tight to her and dropped a hot load deep into her. "Mmmmm", she cooed, "this is only going to get better Tom."

We spent the day making love and I tried on several more outfits. She even helped me with makeup and gave me a couple wigs. She loves to give head, and I can only say there is nothing like being fully dressed and standing in high heels while your mother-in-law sucks your cock.

This all happened three years ago. the boxes never made it to Goodwill. We continue our kinky affair to this day.