My first experience

Every story begins somewhere, so tell us how you got started crossdressing. Only one (1) topic per member, please!

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Bobbie Roberts
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My first experience

Post by Bobbie Roberts »

Maybe this should have gone in the new members section ...anyway, here it is..

My first experience….

I was about 13 or 14 years old as I recall. I was living at home and on this day, I was sitting in the living room, reading the evening newspaper. My parents were getting ready to go out for a formal affair: my Father was upstairs and my Mother was downstairs. Our house was small, a 1 ½ story Cape Cod style house, 2 BR + bath upstairs and the 3rd bedroom and powder room was downstairs adjacent to the LR. All of my fathers stuff was upstairs and all of Mothers stuff was downstairs in the 3rd bedroom. As the affair they were going to attend was formal, Father was dressing in a tux and mother was dressing in a ball gown. Mother had also gone to the salon earlier and had her hair “fixed” for the occasion.

Sitting in the living room, reading the newspaper, I heard dressing type noises coming from the 1st floor bedroom that Mother was using. She had already applied her make up and touched up her hair so that could not be the noises I heard. I had heard a soft snapping / “popping” and puffing noises along with a quiet sigh and some more popping noises. After a few minutes, Mother emerged from the back bed room, wearing her new high waist long leg panty girdle (the sounds I had heard was her struggling to get into the girdle even though it had a zipper – the girdle, I would later find out, was a Poirette # 1578 style) and stockings; she had also elected to wear a merry widow strapless long line bra, which she held against her and asked me to “please fasten the hooks – on the “tight setting”. The dress she wore had a fitted bodice, which required the merry widow bra.

While I was fastening the bra hooks (there must have been at least 18 hooks and eyes), I inquired as to the comfort of these items and what they feel like to wear. She was frank in her description: the high waist long leg girdle felt very tight when it was first put on but after a few minutes, it felt “just right” and “held me in nicely”. As for the merry widow bra. It also felt tight initially, but also became “just right” after a brief period of time. I asked if sometime, I could try them both on and see how they feel for myself. Her answer was: “We’ll see…maybe someday”.

A few days later, I was again reading the morning paper in the living room and Mother was in the kitchen cleaning up after breakfast; Father had already left for work. When she finished with the kitchen chores, she asked: “did I still want to try on the high waist long leg girdle and bra”, just to see how they felt? I answered; “sure”. When I was younger, I was a little on the chubby side. I had developed a little “pooch” tummy, a sort of a soft and jiggly tush and a “midriff bulge” (best described in the current vernacular as a “muffin top”). These issues were the driving factor into the request to try on a high waist girdle and bra.

I went to the back bedroom where she had laid out the same Poirette high waist panty girdle and bra on the bed. She suggested that I put on the girdle first, followed by the stockings then the bra. As I was somewhat self conscious about the situation, I gathered up the girdle and went to the first floor powder room to attempt the put on the girdle. As I was “new” to the experience of trying on a girdle, I did not really know how to do so; I was instructed that the girdle’s zipper was on the left side, just step into it and to just sort of gently work it up, until the girdle was in place. I had not removed my underwear prior to attempting to try on the girdle; I was wearing boxer type shorts. The failure to remove my underwear caused much difficulty while attempting to “just work it up” (the girdle). The girdle just caused the underwear to bunch up and after several attempts, it appeared as if the girdle had “won” the battle. There was a soft knock at the door and Mother inquired how things were going. I related my difficulties with my underwear. She suggested that I remove my underwear completely and that the girdle will take the place of underwear and provide all the smoothing and holding power needed and my underwear would “just get in the way”. I said : “Oh, I did not know that” and proceeded in that direction. After a few more minutes and surprisingly, with a little more effort, I had the worked the girdle on, a little at a time, gently tugging and pulling each side until the girdle was in the proper position. I then proceeded to fasten the four hooks and eyes under the zipper and then closed the zipper and adjusted the legs down. The feeling was euphoria!....not really what you would call tight (it was) but more like a firm, all over compression. As I was a little on the chubby side, the girdle made my tummy absolutely flat; my bum was smooth and rounded and firm, and, my “midriff bulge was also gone! I was initially conscious of the tightness the girdle provided but, overall, feeling was great.

I came out of the powder room wearing only the girdle, feeling a little self conscious, but wonderful. Mother was waiting in the bedroom; she asked how did the girdle feel (firm and tight and wonderful…this is how it was suppose to feel?). She asked if I ready to try on the merry widow bra. As I did not have any breasts to speak of, I would not be able to fill up the cups (she had D cups) but I could experience the rest of the bra and how it felt. She also suggested if I did not want to try the merry widow, I could try a Playtex “living” longline bra; as this may be a little easier the first time. I went with the suggestion of the Playtex longline bra. As I slipped my arms through the straps and placed the bra around me, I turned so she could fasten the hooks and eyes. She asked if I wanted her to use the “tight setting”….answer…YES. After a few minutes of pulling and tugging, the bra was on. With a little more adjusting of the bra, I almost was able to fill up the cups (later I found out the bra was a C cup)

The feeling was indescribably wonderful; the bra and girdle combination totally reshaped me into a curvaceous person…..my pooch tummy was gone, my midriff bulge was gone and I was smooth and curvy. By now the initial tightness of both the bra and girdle had diminished to only a gentle firmness. She said this is normal and after a half hour or so you will not even notice that you are wearing a bra and girdle.

After a few minutes, she asked if I wanted to get undressed yet. I responded: “not yet…can I wear the bra and girdle for a couple of hours?” She said OK, but after wearing them that long, you will be accustomed to their support and when you take them off you will probably feel a little “flabby”. I continued to wear the bra and girdle (and, eventually I had attached stockings to the girdle’s 6 garters to hold the girdle in place) for the rest of the morning and afternoon, for approximately six hours total. When I eventually undressed, she was correct, I did feel flabby and “loose” and could not wait until I once again dressed.

This feeling is still with me after all of these years, which is why I enjoy dressing; starting with a “good” girdle and bra (longline style of course). In trying to define exactly what a “good” girdle is, one can only note is what they prefer and provides the degree of control wanted/needed. My choice is a firm high waist long leg panty girdle, with or without a zipper. This longline bra / high waist panty girdle combination works for me, although some may think of it as over kill or too much support, I find it just right, as it provides the smooth bust to thigh shaping I like. My choices of girdles vary; I like the Playtex 18 hour, the Playtex I cant believe is a girdle girdle, Poirette, VaBien, Rago, Custom-Maid, etc. My choice in longline bra are: Goddess 1304, Elilia front hook, Cortland, Rago, etc. Whenever I dress, I always wear a longline bra and high waist girdle (usually a panty girdle but I have worn the Rago 1294 open bottom girdle, which offers very good support and comfort). I use this combination with a LBD + black stockings and 3” pumps or with a sweater dress combination, stocking and 3” heels. These combinations suits me to a “T”.

Please excuse the ramblings…but you asked …sort of….
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Post by Pat »

Bobbie, Thank you for that wonderful story. I never had an opportunity like that to try girdle and merry widow bra =D> =D>
Keeping them cupped comfortably.

-Pat
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Erica S
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Post by Erica S »

Thanks Bobbie for sharing that story with us,


Hugs,

Erica
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Absaroka
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Post by Absaroka »

This is one of the more unusual first experiences posted here, mostly in the subject of age. Not many mothers would be quite so amenable to helping a teenage boy try on their lingerie. It makes me wonder what was happening at an earlier age, did you wear some of her other clothes for example that were not lingerie so you didn't think of that as crossdressing?

Zari
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DonnaT
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Post by DonnaT »

Hi Bobbie, -wel- to the forum.
DonnaT
Bobbie Roberts
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Post by Bobbie Roberts »

Absaroka wrote:This is one of the more unusual first experiences posted here, mostly in the subject of age. Not many mothers would be quite so amenable to helping a teenage boy try on their lingerie. It makes me wonder what was happening at an earlier age, did you wear some of her other clothes for example that were not lingerie so you didn't think of that as crossdressing?

Zari
Zari,
To follow up to your query re "earlier" .... A year or so, prior to asking her to try on her bra and panty girdle, I had "dressed" for a Halloween party (naturally as a young lady as this just felt right). I had used a wig and make up and a very old "house" dress along with 2" hi heels. I received some applause but also a few jeers. Oh well... can't please everyone....except me. -

Later on (but before making the request to try her bra and girdle), I was looking thru some women’s fashion magazines while waiting at the dentist office (Harpers Bazaar, Women's Day, etc) when I came across bra and girdle advertising. The pictures always depicted a woman dressed in, what appeared to be a substantial high waist girdle (usually and open bottom style but later most of the ads were showing a panty girdles) and a very supporting bra. The copy read something like: "provides firm tummy support that is comfortable for hours; firm slimming panels providing hours of comfort; firm tummy and hip support, etc. The reference to firm support seemed to be in every ad. What did firm tummy (and hip and tush) support with comfort mean? What did it feel like? Why were these aspects important to a woman? Could these garments be worn all day (presumably so or at least for several hours).

As I had noted before, I was overweight with a poochie tummy and a soft "jiggly" tush and midriff bulge. Could these areas be corrected (at least temporarily) with the proper high waist girdle and bra; according to the ads, presumably so.

As she was dressing for this fancy outing with a ball gown, new and substantial underwear was in order. The high waist panty girdle she had selected was the Poirette Style # 5780 (I believe I had incorrectly stated the style previously). This girdle was made from a light weight material but had heavily reinforced tummy panel and satin down stretch side and back panels and a zipper. This is the girdle that I had put on; the longline bra that I tried was the Playtex "living bra". She had no Issues with being asked to try on her foundations and actually instructed / helped me into them. To this day, I believe that looking good and dressing correctly requires a “good bra and girdle” of the wearers choice to correct what ever figure problems need corrected. Feeling good also affects how you look as well. A bra and girdle helps me feel good.

As I have noted before, over the years, I have worn many different types of longline bras and many different types of girdles. Although I have worn open bottom girdles, my preference is a high waist panty girdle (I just like the way it feels); I like the various Poirette styles or the Custom Maid remakes), of course Playtex (18 hr, ICBIAG, and Double Diamonds), Rago, “Subtract” Band top Panty, Sears and Penny’s equal to the Playtex styles, Gossard Answer and a real favorite – Cupid Duotrol (crushingly tight when first putting it on – a pull on style no zipper) but offering substantial firming and control that actually is very comfortable, even after 10-12 hours of wear.

When I dress (a couple time a month), I wear age appropriate conservative clothes; fitted suits, sweater dresses, slacks with knit tops, knitted dresses, 3” hi (max) shoes, all in conservative colors and cuts….but ALWAYS with the proper longline bra and girdle, with stockings, of course.

Not sure if I answered your question…..

Bobbie R
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Michelle Miller
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Post by Michelle Miller »

Bobbie, that was a beautiful story, thank you for sharing it with us.
-Michelle-
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Leeza
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Post by Leeza »

Bobbie, I enjoyed your story and expansion on it. Thank you for taking the time to share it with us.

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Absaroka
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Post by Absaroka »

Thanks for expanding.

My question had to do with the idea that many mothers might not be that surprised by a younger boy asking to try on their clothes, but for it first to appear at puberty would be unusual. So I thought probably your mom had an inkling from things that had happened in years past.
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Post by ArleneMcCarthy »

When I was about 8 when I put on my mothers elbow gloves, hose, and heels
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