Remembering Babysitting

[Kristen Marie]

Some of my best crossdressing memories as a teen came from my babysitting experiences. Alone for hours in the house of my aunt or other females whose kids I sat for, it was always a joy to find unique pieces of lingerie. Most stuff was just hanging up in the bathroom practically with my name on it. (Today I look back on it and can't believe I would actually wear them, but at the time I thought it was OK.)

One item that I loved (and I have not found today) was the bra slip. It was made popular in my late teen years and was a combination of a bra and a slip, usually worn under a short dress. The bra was usually very cushy and the slip was very soft and loose fitting, not like the Spanx or body shapers of today. The feel of it on was amazing. I distinctly remember this one woman having about a dozen of them.....and they all fit.

Were there any special items you recall from those days?

[Deborah Jane]

I remember having to look after my aunts cats when she was on holiday once when i was about 14. [I had to feed them and groom them]
I couldn,t resist looking in her closet and hanging up was the wedding dress she had worn a year earlier.
I just couldn,t resist trying it on and i guess one thing led to another, with me eventually spending the whole afternoon round there and dressing in the whole bridal outfit including underwear and even her garter.
Even now i treasure the memory of that day :daydreaming:

Needless to say, during the rest of that week i tried on several other outfits too!!

[AmandaM]

Well there was this beautiful young woman who had me housesit for two weeks once when I was 15 in the 70's. She had a liking for short dresses, ala Marcia Brady. Did I do it? I'll never say!

[Angie G]

My wife had one and I loved it wish she still had it.:hugs:
Angie

[Tina Dixon]

I had a chance to baby sit once and said no and missed out on those fun things I guess.

[leesametz]

i never babysat but i did use to stay with a neighbor so she wouldnt have to stay in the house alone at night. heres the story i posted elsewhere on the net. with some editing...


All the time I was growing up, my old widowed next-door-neighbor had a roommate. When her older roommate got married, my sister started to stay there every night. The neighbor didn’t like having the house to herself. When my sister left for college, the neighbor tried to get some local co-eds to stay for a minimal amount of rent.

I stayed there on an off for about 5 years myself. The neighbor would pay me $1 a night and since I had a double bed (more room), she was older (kept the house warmer in the winter) and I was out of my parents house it wasn’t a bad deal.

This story relates to a time when ‘Betty’ had a roommate from the local college who had gone home for the Christmas holidays. I was asked if I would stay over. I said sure why not.

I can’t remember the boarders name and I never once saw her. What I did know about her is this: she wore a size 5 panty, her bra size was 36C and her skirts and dresses were size 8/10 (I think). I had stayed there a couple of times throughout the year and had rummaged around in her panty drawer many times.

During these ‘fill-in’ nights I would slip on her nylon panties and her pantyhose to sleep in and quite often I would hook a bra around my young shoulders and stuff them with socks. Of course I always would end up highly aroused...

A couple of days the neighbor had appointments early in the morning and I would always opt to sleep in. As soon as she pulled out of the driveway I would be pulling lingerie out of the dresser. One time I took out the pair of navy sheer to waist pantyhose I had worn numerous times in the past, a full nylon slip, the only nylon bra in the drawer and the required amount of socks. I slipped this all on and caressed my slickly sheathed body until I could barely contain myself anymore. I stopped and opened the closet and pulled out a somewhat fancy blue knit jersey dress. I stepped into it and felt a great rush of excitement. I believe it may have been the very first time I was completely dressed. She must have had size 4 feet because her shoes were doll sized. The hair, makeup and the shoes were the only missing pieces.

I proceeded to walk around the house, up and down the stairs, sitting down, standing up, the whole deal, for the next hour or so...

i really would have liked to try on her shoes but they were absolutely tiny...

other times, i had rooted around in 'Betty's' drawers after i found some old open bottom all-in-ones hanging in a closet in the bathroom. i dug out a couple pair of garter stockings and had a pair of my sisters nylon satin panties. i would sneak this stash into the bathroom late at night after Betty had gone to sleep and would dress up. i think it might have been part of the reason i love girdles and stockings so much now...

[Kimberly Marie]

Hi....my sister hated babysitting. So I use to all the time. I loved it. My parents had lots of friends so I babysat alot. Not only was it fun I made alot of money, for being a teen at the time. Now I'm a single parent have been for the last four years..........hehe......:)

[daviolin]

I never baby sat. I didn't get along with little kids very well. But I used to watch a neighbor's house in the summer time when they went on vacation. Oh Boy let the party begin. I think I was about 13 years old. They had a teenage daughter so off to her room to check out my summer wardrobe. And oh boy it was a motherlode of pretty things. And what was so cool her size was perfect. From bra size down to her shoes. My favorite outfit was a pink ruffly blouse, a short tight black skirt, Black garter stockings with a garter belt. I thought I died and went to heaven when I found that. And a pair of black high heel pumps. I still to this day fantisize about that event. I almost got busted by my Mother. I was over at the house all morning a little to long for my Mother's idea. She came over to check on me. I was just finishing getting undressed. So that was close. We crossdresser's sure live on the edge.:heehee:Daviolin

[Sally24]

It seemed like everyone wore girdles back then, even the young thin girls. I use a corset myself, but the smooth, comfortable (relative to a corset!) stretch girdles are still an interesting memory. Wore one for a couple hours when I acted in a skit in college. Definitely works well as a gaff!