The seminar started at the local Marriott today. As the lead appraiser for my office, I was the main organizer for it. We had brought in one of the best appraisers in the East to share his expertise in appraising and developing a larger client base. The real estate market on Eastern Long Island was hot and I wanted to capture more of the $$$ it was spreading around.
My name is Gayle. I moved out here from the city 5 years ago with my wife, Linda. Yeah were lesbians, big deal. We're both in our upper 30's and in good shape for our age. Anyway we bought a nice 4 bdrm. home with pool on a quiet cul-de-sac, 3 miles from the beach in an area with a thriving gay and lesbian community, and plenty of opportunity. Linda is an OR nurse at the local hospital, and we share our home with Amber and Carol. Amber has her own construction
company and Carol owns a local salon.
I met Bill at the hotel and showed him the set up. We had time before it
started so I invited him for coffee and to discuss the weeks meeting
On the way to the dining room I looked him over... a bit longish hair, a well fitted suit, about 5' 6" or 7". Probably about 45. He hung his sport coat on his chair and we sat and drank our coffee. I noticed his wedding ring and surprisingly, through his white shirt I noticed what appeared to be nipple rings as well. As he lifted his cup I saw he had soft but well manicured hands. In fact it looked like they had a clear or almost pink tint to them.
We talked a little about what he would be teaching over the next few days, then headed back to the meeting room. I figured that with pierced nipples he was probably pretty cool so I told him that I had a home not far away with a spare bedroom and a pool and he could stay there instead of a cold hotel room.
Bill said it sounded like a good idea but he would have to call his wife
and get her ok first. I said fine and he said we could call at lunch
The morning session went well and at the lunch break he called his wife.
He explained the situation to her and said "yes ma'am" a couple of times.
He handed me the phone and said that Mary, his wife, wanted to talk to me.
I told her about the house and that I was gay, and just hoped to pick his
brain a bit more without the meeting attendees around. Yeah I was a
little selfish but it has helped me get where I am in business today.
She told me it was okay for him to stay, but there were a few rules she
had for him. She said he was well versed in household chores and she
should be expected to help with dishes and cleaning. She also said that he is required to obey when told do something. Finally she said she bought Bill a new swim suit that he was to wear for swimming and would love a pic or two of him in it.
I told her I had no issues with that, and gave Bill back the phone. I thought it odd that Mary seemed to have a problem with gender, as she certainly called him "she" more than once in our conversation. I wondered what was up with that and the swim suit comment.
Bill sort of nodded a few more "Yes Ma'am"s into the phone followed by
an, "I promise I'll behave," said goodbye and hung up.
He said that everything was cool with her and he wanted to know what she
told me. I said he was supposed to do the dishes and behave and something
about wearing your new bathing suit. He blushed at that and really had me
wondering what was up with them. He certainly seemed to be a bit
submissive to her on the phone.
When the afternoon session ended, we were free until 3:30 Tuesday. I
suggested he follow me home and he smiled seeing me grab my helmet on the way to the door.
He followed my new Indian cruiser in his Mazda. It was only about ten miles to my home. After grabbing his luggage, I gave him a quick tour and showed him the guest bedroom. At lunch, I had explained my living situation so it was no surprise when I introduced my wife, Linda. She was off most of the week and was lounging by the pool when we got in.
She looked hot in her silver bikini with her long tanned legs. Judging by
his reaction Bill looked impressed with her attributes as well. I took
his coat and said I would put his bag in the guest room and fix us drinks. He asked for a tequila sunrise. I had a beer.
I really wanted to sneak a peek into his suitcase and answer the curiosity his wife built in me about his swimsuit. I knew I shouldn't, but he was outside at the,opposite end of the house and wouldn't hear me open it.
I plopped the case on the bed and hesitated a bit, but then I went ahead and opened it. I moved a couple shirts and then saw some soft pink
straps. How odd I thought and pulled them up slowly. It turned out to
be a cute pink bikini top. Looking further I found a bikini bottom and a
short pink swim skirt to go with it. Worried someone would miss me I quickly replaced the items and noticed a couple of lacy panty briefs and a camisole.
I packed it all back in and went downstairs to the bar and poured Bill a stiff drink, grabbed a Sam Adams for Linda and myself, and and went back out to the pool where they were talking. I was wondering what he would look like in the 3 piece pink bikini, and if he would really wear it if I told him to. Bill and Mary must be pretty kinky, I was thinking to myself. This may be a better conference than I hoped for.
He asked me about my bike and I offered him a ride. He said he would love to but wanted to change out of his business suit. While he was changing, I told Linda about his bikini and the stuff I had noticed in his case as well as his piercings. Linda smiled at that and I also filled her in on the conversation I had with his wife.
She said it seemed we had a submissive sissy girl for a house guest. Linda thought we could
have a whole bunch of fun with Bill so why not take advantage of it. I
agreed and said we would join her for a swim when we got back and see how
he handles wearing the bikini for us.
I asked her to call Amber and Carol and fill them in so they wouldn't be
surprised when they got home.
Bill came out in jeans and a tee. We went out through the garage and I
tossed him a helmet and laughingly told him that he would be riding on
the "bitch seat" and better behave. He said I had a nice bike and he is
happy to be the "bitch" on it. We laughed and headed down the road. I
gave him a tour of the town and then headed by the beach. I pointed out a
gay bar we usually went to on the beach. He asked to stop at a shop on
they beach. He said he needed to stop and get a new bathing suit so he
could swim later as he forgot his. I new he was lying and kept driving. I
told him his wife said she packed him one and he was to wear it.
He was strangely quiet the rest of the ride. We roared back into the
driveway and I told him I was going to go for a swim. I poured him
another strong tequila sunrise and grabbed a beer. I went to change
telling him he had to serve the next round. I put on one of my sexiest
suits and went out and gave Linda a long hot kiss. Bill was watching
while having a drink and a smoke. I turned and told him to go change into
his swim trunks and join us and he blushed, and declined, saying he changed his mind. I told him that wasn't good enough and teased that I would tell his wife if he didn't.
He sort of bowed his head and muttered "yes miss" as he headed back into the house. Linda and I had a good laugh when he was gone and softly kissed.
We were still making out when Bill returned wrapped in a towel.
"Well, drop the towel and lets see the new suit Bill," I demanded.
He unwrapped and sure enough was wearing the pink bikini bottom. We both told him how cute it was but I told him it, "it looks like he was missing some of it."
Before I sent him to finish the job I made him come closer and show us his nipple rings. Moving closer so we could see them better, he informed us that they were an engagement gift from his wife and that she had done the piercing herself.
We also noticed that there was almost no bulge in his crotch so I thought he must have tucked himself back. As he turned to leave and get the rest of his swimsuit, noticed a small padlock hanging out the back of his suit. I pointed it out to Linda and we tried to figure out how that fit into everything.
When Bill returned he was wearing all 3 pieces. We had him twirl for us
and told him he looked sweet. He blushed almost the same pink as his
suit. I sent him back in to get us all another drink. He served us our
drinks and lay out in the lounger next to Linda. We asked him why his
wife got him that bikini and he told us that she thought girls are
prettier and more fun, and she says, "I'm more obedient this way."
I lit a joint and offered him some hoping to relax him more so he would
open up. After a long toke, he thanked us for not laughing and teasing him about the suit, and said how great it was that we let him stay at our house instead of at the hotel. I laughed and told him that maybe we
just didn't start teasing her yet.
"We will see if you feel the same
way in 5 days when the conference is over."
When Linda asked, he said her fem name was Brenda, and that she had been submissive to his wife since before they were married.
A few more hits off the joint and I could see him getting higher and more relaxed.
That's when I asked him about the tiny padlock at his back. He said it held a light weight chain that locked into his P A piercing. He said he wasn't allowed to use his penis like a man but could only rub it between his legs more like a clitoris, But once in a while Mary would let him free.
Brenda blushed when we laughed and said we agreed with her wife.
"They should all be locked up until needed," Linda piped in. "After all strap-ons don't get soft or need testosterone."
I handed Linda a bottle of lotion and told her to spread it on Brenda
because the sun was still pretty hot. Brenda was enjoying Linda's attention, but I forgot to tell her it was a quick tanning lotion, not a
sun block. I lit another joint and passed it to Brenda.
I guess the drink, pot, and hot sun combined to tire her out and she was
soon asleep on the lounger.
Linda and I discussed what we could do to make Brenda more fem during the short time she would be here. We decided to keep him as Brenda unless we were at the conference. That would
be about 5 hours a day that he/she would be teaching or speaking or schmoozing the attendees. We would not do anything that would effect that, but his wife had pretty much given me cart-Blanche with her sissy.
We gently turned Brenda over on the lounger to get her tanned evenly and
went in to start dinner. Brenda awoke about an hour later and jumped in
the pool. When she (I guess she won't be a "he" in our house anymore)came in, I told her to shower before dinner.
Not 5 minutes later, Linda and I heard a loud gasp.
"What's wrong Brenda?" I called up to her.
"That damn bikini left me tanned like a girl!" she yelled down.
I went up to see and when I did, I said, "you looked adorable. A perfectly girly tan for a sweet sissy."
She said she was worried she couldn't go to the beach with the tan lines.
"Oh, don't worry about that we will figure something out. Dinner is almost ready. I will get you something comfortable to wear."
I got her a denim skirt and pink bra and tank top that would look cute on her. She balked at first and I just said "It's okay Brenda, we are all girls here, you should enjoy yourself when opportunities like this come around. It's not like we don't both know what a stuffed shirt business we work in. Now promise me you will relax and just be Brenda while you are here. I wouldn't want to have to give Mary a bad report."
Linda and I both smiled as she came down to dinner wearing what I left out for her.
As she neared the dining room, Carol walked in the door, saw a startled Brenda, and said, "well who's the new bitch?"
"That's not a Bitch, that's our sissy house guest, Brenda," Linda told her.
"She's cute, but she needs a little make over. Don't ya think?" she said with a grin.
I told her to wait until after dinner and introduced her to Bill who was blushing away. I explained she would be giving the keynote address at the conference and will be staying with us for the next few days.
Amber came in from work a few minutes later, and we went through the whole intro thing again with her. We
introduced her to Bill/Brenda. She shook his hand and, kissed Carol and sat down to eat. After dinner we relaxed a bit and I decided we should take Brenda to the bar.
Brenda said she would need to change first and Carol told her she would help, and led him down the hall to a room he hadn't yet seen.
Upon entering, Carol said it was her home salon and that she used it to do
Amber, Linda's and my hair. Bill was balking, saying she meant to go to her room and put on a mans' shirt and jeans.
Carol adamantly told her that won't do as they were going to a women's bar and she was going to do your hair and make-up.
When Bill started to protest, Amber, at 6ft. tall, got up and suggested he do as he was told. "Did you already forget that Gayle said you would be en-femme when not at the conference?"
As she was about 4" taller than Brenda, and probably stronger, with a whispered, "yes sir", to Amber, he returned to the beauty chair.
I called Brenda's wife and filled her in on the day's events. She was
pleased about his wearing the bikini and said she couldn't wait to see
her tan. She said to, "take a free rein in dressing him, but to make sure he could still appear normally in work situations. We talked a bit more, and agreed to talk more the next day.
I went in to tell her and Carol what Mary had said. Bill blushed and
Carol smiled and said she knew just what to do. Amber reentered the room
with a few long straps and bound the sissy securely to her chair. Carol
told him to behave so she could get to work. She started thinning and
arching his eyebrows, but not too much.
She combed out his hair and started to trim it a bit before using a curling iron to give him a prettier style, then did his toe and fingers in a nice bright summer red.
As she was working I told Bill that she would of course be Brenda for the rest of her stay and she better get used to it or the polish would stay on his fingers tomorrow. (I wouldn't have made him do his seminar like that but he didn't know that.)
I told him I would be having more discussions with Mary and he had better behave himself. Carol finished his makeup and added 2nd earring to her already pierced ears. When she released him he probably looked
better than he ever had before, but, due to her masculine features would still be made as a male.
I had Brenda take off the tank top and gave her a lacy dark red top and
cinched in her waist with a snug 3" belt. Amber had a pair of strappy
open toed pumps that fit her well and we were ready to go.
We hopped in Brenda's car and headed to the bar. Once inside, we said hi
to the bartender, Janet, and headed to a table. Janet was a dear friend
and was one of the bar's owners.
I told Brenda to go to the bar and get our drinks. I could see some heads turn as she walked to the bar, even a couple of whistles and a very clear "Hi Sissy" from one of the patrons.
I could see Brenda blushing from my seat. She returned with the drinks on a tray and served us all then sat down. After some small talk I took Brenda onto the patio to have a smoke, and showed her the private beach the bar owned, as the last of the daylight faded. I pulled her to me and forced my tongue down her throat. We kissed for a couple minutes and she melted in
my arms. She gasped as we parted and asked why.
"Because I wanted to feel
you submit and get all frustrated you silly sissy," I told her.
She thanked me and we headed back in.
After we rejoined the table Janet came over to get the tray. She
mentioned that one of her waitresses had called in sick and she was short
handed. She said Brenda looked like she knew what she was doing with a
tray in her hands earlier and wondered if we would let her fill in as a cocktail waitress for a few hours.
"It would be neat to have a sissy serving the ladies in the bar. And you guys can drink free all night if you say yes."
Brenda was moaning about if not being fair and blushing at the same time. Amber, Carol and I looked at each other and all nodded in agreement. I told Brenda to get her sissy as up and get to work. Janet took her to the office for a minute and she came out with a pretty frilly apron and a tray and started walking the floor taking orders. She gave a huge blush when the DJ announced that Sissy Brenda would be filling in as a waitress for the evening and there was a big laugh from the crowd of about 150.
Brenda was busy constantly, but did remember to come by and get our order
now and again. The 3rd time she came by she was complaining about the
heels and how her feet were hurting. I had enough to drink by then that I
just told her to shut up and do her job or I would pull her over my lap
and spank her in front of everyone and then she wouldn't worry about her
feet as much.
The evening was going well and Linda and I danced a bit and walked on the
beach for a while. When we got back to the table Brenda came over, put
her tray down and said she didn't think her feet would last much longer.
I reminded her what I said earlier and she shook her head and said she wouldn't let that happen.
She forgot about Amber apparently.
Amber got up, grabbed her hand
and pulled her arm behind her back. I moved my chair out and Amber pushed
her down over my lap and pulled her skirt up revealing her pink pantied
ass. I started swatting her and when she started to squirm Linda hopped
up and stood with Brenda's head squeezed between her legs keeping her in
place. A crowd gathered to watch, cheering "Spank the sissy! Spank the
After about 10 minutes I relented and told her to kneel. I asked her if she was ready to return to work and she said she was. I told her to
apologize for causing a scene and to kiss Amber's, Carol's, Linda's and
my feet and hop to it. As she went back to work the gathered crowd
cheered. I don't know which was redder, her face or ass.
By 1 am we were getting tired and had Janet release Amber form her duties
and got ready to head home. Janet joked that she hadn't even cleaned the bathrooms yet. I said maybe another time.
On the ride home Brenda said that she really did have fun and that after the spanking she was actually treated much better by the gals at the bar and even got about $80.00 in tips.
Once home we all pretty much went straight to bed. Bill had to do a
morning seminar, Amber and Carol had work and I was going to the seminar.
I gave Brenda a nightgown to wear and kissed her goodnight, then joined
my lovely wife for some hot sex before falling asleep.
The next morning we removed Bill's nail polish and we went to the host hotel for his seminar. I spent so
much time thinking about the rest of the days plans that I wasn't paying
much attention, but I had plenty of time to talk business with him anyway
so I wasn't worried. We left after lunch and headed back to the house.
It was a gorgeous day so I told Brenda to get ready for the beach. She said we should just use the pool but I told him no way. It was to nice a day and there were too many beautiful people to watch at the beach.
She whined that it would be too hot having to wear a shirt to hide the tan lines and I told reminded her that she was back in female mode and that she would just have to wear her bikini. When she balked I picked up the phone and asked what his wife's phone # was.