My Wife/Mistress has an older lesbian friend that lives a couple miles from us. She has a lovely
large private infinity style pool that we use frequently. Lana knows how our relationship is built
and that I dress femme regularly. I am her "pool girl", responsible for keeping the pool spotless
and the decks and equipment running well. Of course this is always done in one of my many 2 piece
bikinis. And for a TV that loves being a sissy what could be better. If it didn’t need cleaning I
would just go over and swim all day and work on my pretty bikini tan. hee hee.
Lana was having a pool party and Mistress Ann and I were attending. The other guests were all older
lesbian friends of Lana's, some we have met before. My job was to be sure the pool was great and
also do the grilling and serving. It was a pretty vanilla affair. I did get to swim a bit but the
ladies kept me pretty busy with cooking and filling drinks and cleaning up. It was a fun time and I
was enjoying my role throughout. I just wish it was going to be a bit sexier. Oh well, maybe next
About 10 days later Mistress Ann called me into the den and told me that one of the gals from the
party called and asked for us to attend a party at her home the coming Saturday. Mistress had told
her we would and apparently the host, Karen, had asked her a favor. I figured she wanted me to
dress more like a guy. But no, apparently Karen enjoyed my service at the pool party and she
wondered if I had ever served as a cocktail waitress serving drinks and hors d'oeuvres. Ann said she
thought it would be a kick to have a sissy cocktail server for her guests, about 20 or so.
Mistress responded that i was well trained for that and said I had a perfect little black and pink
maids outfit that would be perfect for it. She told her about the pretty fluffy petticoats that
went with it and that I had lovely heels to wear with it. She told me that she pressed Karen a bit
because the pool party seemed so vanilla was she sure that's what her guests wanted. Karen
apparently confirmed that her friends were a bit more exotic in their tastes and it would be just
right for them. In fact the sissier the better was her attitude.
So Mistress Ann decided that we would go as invited, her as a guest, me as the hired help, so to
speak. In fact i was to be there 2 hours early to help Karen get ready.
On Friday night, the day before the party Mistress told me that she had talked with Karen again to
be sure everything was in order for the party. She had a concerned look on her face and i wasn't
sure why. Starring coldly at me she said that one of Karen's friends said that at the pool party
she entered the bathroom after i had left it and found the toilet seat up. It was totally
unacceptable at a lesbian get together and she wanted to be sure it would not happen at her party.
Mistress assured her it would not. She told me that I would be punished for the infraction and a
few others as soon as she decided on something appropriate, and that I had better be on my best
behavior tomorrow night. I promised her I would and finished cleaning the kitchen before preparing
Sat. morning Ann woke me early and called me to the kitchen. Breakfast was waiting and she directed
me to eat while it was still hot. Bacon and eggs, pancakes, OJ, and coffee. I guess she forgot
about punishing me. I mowed the lawn and Mistress came out and with ice water and brownies. Not
like her at all, something must be up I thought.
At noon she called me into the kitchen for lunch. I was heading for the bathroom and she told me to
eat first. I said I had to go to the john but she insisted. At my chair was a large bowl of oatmeal
and a grilled cheese and tomato sandwich, a glass of milk and more coffee. I finished it all at her
instance. I was trying to tell her I was full but she said it was insulting for her to cook a nice
meal for me and my not finishing it. She then refilled my oatmeal and said to finish it too. I felt
very overstuffed. I asked if I could go to the bathroom now and she said I could only pee. She
actually stood at the door and watched me to make sure and told me that not pooping was part of my
I really needed to go and asked her again but all I got was the "look". Yes that look. I knew
better than to ask again. I did some housework while she relaxed and around 2 o clock she told me
to take a shower and do my nails to start getting ready to go out. I took a long leisurely shower
trying not to think about going to the bathroom. I shaved my light facial hair smooth and got out
and wrapped up in a nice soft towel and sat down to do my nails in a dark pink to match the trim on
my maids outfit. Mistress Ann was so nice to keep me company and chat while i did them. She even
fed me about a half a Hershey bar as I polished my fingers and toes. I was finally done and letting
them dry. I asked her about the chocolate as it didn’t taste like a regular Hershey. She told me
that it wasn’t a Hershey it was a chocolate exlax bar. I looked at her astonished and reminded her I
had to serve the party tonight and worried about the effects.
She just laughed at me and said that was nothing, the oatmeal was laced with laxatives too. She
said if i was a good girl and outlasted the party she would forgive my errors and even unlock my
chastity for a full week. As good as that sounded I knew from past events that the odds were
strongly against her having to do that.
When it was time to dress she led me to her bedroom and layed out on the bed was my maids dress,
petticoats, thigh hi stockings and an old pair of pink satin granny panties. Now before we dress
you I want you over here she told me as she sat in her vanity chair. Before I could react she
pulled me over her lap and pulled my arm up behind me. About 10 Quick hard slaps to my ass had my
attention. Mistress informed me that I was to be at my best this evening and any screw ups would be
dealt with harshly. She said I was going to go with a very sore bottom to start and warned that i
wouldn’t want to dare make it worse. She reached into a vanity drawer and pulled out a piece of
coarse sandpaper and used it all over my ass and crotch, all the way down between my thighs. My
ass was burning almost immediately from this treatment. Then she took a spray bottle from her
vanity and wet my bottom all over. The cool water felt nice, until she took her wooden hairbrush to
it. She gave me a full 40 stinging swats on my wet bottom enjoying the glow form my bruised bottom.
She pushed me off her lap and spread her legs and told me to get busy. I licked her savoring her
sweet taste as I felt my ass on fire. She was totally drenched and came strongly in just a few
minutes. She collected herself after her massive orgasm gave me a hug and and said i needed to
dress. She handed me the satin panty and an extra thick Maxi pad with wings and I put in place then
pulled them up. Next was the white thigh highs with the pretty lace trim and hearts all over them.
They felt so pretty on my smooth legs. Next the petticoats. They were thick and fluffy and would
hide the small bulge in my panties caused my by steel chastity. Chin in hand, Mistress Ann studied
me for a second then told me to take off the petticoats.
As I was pulling them off Mistress went to a closet and came back with a disposable diaper and
fastened it around me, taping the sides closed and adding some extra tape to the seems. That will
insure you don't remove them. Still not satisfied she grabbed another diaper. This one custom made
pink cloth with 20 layers in the crotch and guaranteed to hod at least a gallon without leaking. I
forgot we still had them and was starting to worry. I would have to waddle on my heels with that
between my legs. I was made to lay down and Mistress pinned it on tightly, left and returned with a
pink plastic diaper cover. I started to complain and was told i would go without a maids dress if i
complained. Yes Mistress, thank you for my diaper mistress. She said that would satisfy Karen that
i wouldn’t leave a toilet seat up again. I put on my petticoats, lightly padded bra to bring my A
cups up to about a B, and slipped on my heels and dress with apron attached.
Some eye shadow, liner and mascara and a bit of rouge was next. I asked about lipstick and was told
I didn’t need it and i would find out why later on. That had me confused but I let it go. Best not
to question Mistress Ann. I reached down and found out i couldn’t even feel my chastity through the
pettis and diapers. It was going to be a long night. I was told it was time to go and mistress
handed me my purse. At the door she told me she had a couple of rules for me tonight. Firstly I was
not allowed to talk. I was to obey Karen as well as herself. And if I could get through the night
without messing my diapers I could take it off when I got home and use the toilet. If not I would
spend the next 3 days with no toilet privilege at all. You can think about that as you drive to
Karen’s. I will see you there later. And she shoved me out the door.
I got to Karen’s a little after 5 and she greeted me with a smile. As I entered her lovely home she gave me a quick tour so I would know where to find things and be able to direct guests to what they needed. She told me to lift my skirt and show her how I was dressed. She laughed at my diaper and said it was a nice touch. She said everyone will love knowing that the sissy maid is really a sissy baby. We went to the kitchen and she outlined my tasks for the night and instructed me to start filling platters with snacks and hors d'ouevres. I took to the task and readied the buffet table as well while she dressed. It was almost 7 and guests would be arriving soon. I was given a few minutes rest and a small salad. Just my luck I found out the salad dressing was spiked for me as well. I felt a few rumbles in my belly as the door bell rang for the first time.
I invited the guests in and told them to make themselves comfortable and took their drink request. More were arriving including my lovely Mistress Ann. By 8 o'clock all expected guest had arrived and I was working the room properly. Mistress Ann called me in to the kitchen and with Karen at her side said that she understood I was overheard talking. I tried to say I was just pointing out how to get to the dining room but was told to be quiet. Mistress reached into a bag and pulled out a weird toy. It turned out to be a gag. When it was attached to my mouth I found it very effectively silenced me, but it had a hollow tube passing through it to allow me to breathe. It was also painted with a pretty lipsticked smile on perfect white teeth from the front. The strap was locked behind my head and would not be coming off.
Telling Karen she would love to show her how effective it is she hooked a long large funnel to a plant hook on a shelf and attached the hose at the end to the front of my gag's breathing tube. Taking a bottle from the bag she poured about a quart of it into the funnel. It immediately flowed to my mouth and I had no choice but to drink as fast as I could. She told Karen that it was just baby formula but had diuretics added as well. When I finished drinking I was sent back out to serve the guests at the buffet, gagged and silent. I almost doubled over from cramps at one point but was able to hold back. Finally the meal was over and I was allowed to clean the platters and tables off and return to the kitchen for a break.
I was called back to the party room and began serving drinks. As I walked around I noticed the funnel bottle had been move to that room. The women were gathering around me and Karen told me that the lady's all wanted to see my diapers. I had to stand there and lift my dress and pettis so all could see. I was red faced doing this and soon was pushed forward until the funnel could be reattached to the gag. The liquid was released and it had been filled with warm urine. I had no choice but to drink, fighting cramps in my belly and trying not to fill my diapers. They were already wet from peeing and my bottom burned where mistress had paddled and sanded it raw earlier. Of course I had no choice but to drink everything that flowed, and finally the flow stopped. Some light applause and laughter when it was empty.
I was hoping to be released from the funnel as someone came up and started tickling me saying something about a ticklish baby. As I tried to twist away others held be in place and I lost control. My bottom could hold back no more and as I was tickled I felt if oozing uncontrollably into my diaper. I was on the verge of tears and Mistress Ann stepped up and disconnected the hose and forced me down on my diapered bottom to the floor. She knew what happened and laughed out loud as I plopped down and they all heard my mess squish around me. The room erupted with laughter at this point and I heard all sorts of messy baby girl comments. I was crying now and mistress said it was okay and I did just what every one wanted.
She gave me another out saying that if I could guess who pissed in the bottle I could go home and change and my punishment would be over. I had 2 guesses. I guessed Mistress of course and was wrong. The others couldn’t possibly have done it so it was obviously Karen. Shit wrong again. I turned out to be a young lady named Paula that said she always loved having people drink her pee. I was told to stand and brought to the guest bathroom and told to sit on the floor. The funnel was hooked to a towel rod. I was blindfolded and told I would spend the night in the bathroom as no one wanted to have the smell in other parts of the house. Furthermore anyone that wished was welcome to use the funnel instead of the toilet.