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In part 1 I came home to see my daughter Amanda crying. She was upset because she was going to miss a mother/ daughter weekend because my wife Lacey had a work emergency and could not get away. She somehow convinced me to dress up and go as my wife. With the help of Lacey and Amanda I made a very attractive woman.
I later learned that my Amanda had bet my wife that she could get me to suck a cock. She had two of her friends buy me drinks at the hotel bar, get me drunk and take me back to their room. Moments later as I was giving them both blow jobs. Lacey and Amanda entered the room and took pictures of me sucking cock.
To add insult to the situation Lacey fucked the two men and had me lick their cum out of her pussy.
Finally the two boys. Steve and Jack, kissed us goodnight and thanked me for sucking their cocks.
My wife, daughter, and myself retired to our hotel room. The room had two queen beds and a couch. Lacey decided that I should sleep on the couch. With my hair and makeup a mess I was in no condition to argue.
Lacey asked Amanda. "How did you know that your father would suck cock?"
"I thought he had sissy potential. The way he stared at me when I put on lipstick seemed to turn him on more than it should. Then I thought some of my sexier panties seemed a bit stretched."
"That made you think he would suck cock, I'm impressed with your detective and logic skills."
"Then I was at school one day and I overheard Steve and Jack talking about picking up and fucking sissy men. We started talking about my suspicions about dad. They helped me hack his computer to see what porn he watched, then they offered me $1,000 if I could get dad to suck their cocks, $2,000 if they fuck his virgin ass.
Then once I saw how excited dad got when he put on panties and stockings I was pretty sure I was right."
"Wow, maybe we should have waited before we went to their room. You might have made another $1,000."
"We still have the rest of the weekend."
"I don't want to get fucked in the ass. The only reason I sucked their cocks is because Amanda tricked me, left me alone at the bar, and her friends got me drunk."
"Stop whining." My wife said. "Now put on this lacy nightgown and go sleep on the couch."
"How about that lipstick blowjob you promised me?" I asked.
"I promised you a lipstick blowjob, I didn't say I would give you one. I'm pretty sure I walked in on you giving two young studs lipstick blowjobs, so it looks like I kept my word."
I was still a little buzzed from the alcohol, and I was getting very tired. I put on the sexy nightgown and tried to get some sleep. Lacey and Amanda were sharing some laughs. Amanda was clearly happy that she managed to pull off her grand plan and was trying to figure out how she was going to spend her money.
When I woke up the next morning, part of me was hoping that last night was just a dream. But instead I had a bit of a hangover.
I asked Amanda. "Now that your mother is here can I go home?"
Lacey answered. "Of course not. Amanda has such a nice day planned for us. There's a Victoria Secret fashion show this afternoon. Before then you and I are going to get massages and facials at the salon.
Amanda says. "Steve and Jack just invited me and Brianna to lunch."
"I really don't want to see them."
"Please, is that anyway to talk about the young men that let you suck their cocks last night. Mom, should I ask if they have a friend for you?"
"That's ok honey, why don't the four of you go out. I am going to hang out by the pool. I noticed this hot young life guard yesterday. I hope he notices me in my brand new bikini. Meanwhile I'm starving, let's get dressed and get some breakfast."
"I have no male clothes. Please don't make me spend the day dressed as a woman."
"Not the day." My wife answered. "The whole weekend, Brianna. Your daughter has bought such nice clothes for you to wear. You wouldn't want to disappoint her."
Amanda opened her suitcase and handed me a pair of lacy panties. "Put these on Brianna."
After putting on the panties and some stockings my wife and daughter noticed that I had an erection.
"And you said you wanted to wear your male clothes." Lacey said. "It looks to me that you still get excited wearing panties."
I couldn't really argue, and after a few minutes I was once again transformed into an attractive woman.
"Dad looks extra hot this morning." Amanda said. "I really love his shiny pink lipstick."
"Yes, she does look very pretty. Must be the after glow from sucking her first cock. Maybe you should stop calling her dad. How about, step mom."
"You are right. Step mom looks extra hot this morning."
"That's better."
As we go to breakfast we get a lot of looks from the men in the lobby. I'm a little uncomfortable, but Lacey and Amanda seem to enjoy the attention.
During breakfast Lacey and Amanda are flirting with our waiter. Then they try to embarrass me by asking each other which men they thought had the biggest cocks.
Finally as the waiter brings the check and asks how everything was, Amanda answers. "Everything was delicious. This is my step mom Brianna, do you think she's pretty? Last night she sucked cock for the first time."
The waiter turned bright red, and said. "Thank you for the tip, have a nice day."
After breakfast Amanda went to buy tickets for the Victoria Secret fashion show while me and Lacey walked to the salon for our massages. As we entered the salon the hostess, Rachel, asked if we wanted a male or female masseuse.
Lacey answered. "I would like a woman, my husband, I mean Brianna, would like a man."
As Rachel walked us into the room she said, "Please strip to your bra and panties, your massauses Jessica and Tyler will be here in a few minutes."
Lacey quickly stripped to her panties, but to the surprise of me and Rachel she wasn't wearing a bra.
Without batting an eye Rachel said. "Nice breasts."
After she left I complained to Lacey. "What are you trying to do embarrass me? The massasuses will know I am not a woman."
"You need to relax, and enjoy your massage. You will love having a strong man having his hands all over you"
Jessica and Tyler walk into the room and introduce themselves. Jessica is very pretty, while Tyler is a handsome man with a very athletic body.
Tyler says. "Brianna please strip to your bra and panties."
Lacey adds. "C'mon Brianna don't be shy. They are professionals they see girls with very little clothes all the time. There is nothing to be embarrassed about."
As I take off my dress Jessica and Tyler notice the bulge in my panties.
Lacey adds to my embarrassment. "Brianna just started wearing panties a couple of weeks ago, she still gets excited when she wears sexy panties and sees a good looking man."
Tyler and Jessica have us lie on our stomachs to begin the massage. Jessica is fascinated by the situation and asks Lacey how she managed to get me to dress up and look like such an attractive woman.
"It was actually my daughter's idea. She thought my husband had sissy potential and could get him to suck a cock."
"Did she?"
"Last night she sucked the cocks of two of my daughter's friend's cocks."
"They got me drunk, I am not a sissy."
Then Tyler added. "Whatever you say Brianna, that bulge in your panties say differently. Just relax, I promise this will be the best massage you've ever had."
Tyler starts working on my neck and shoulders. His strong hands feel amazing and I start getting excited all over again.
I look over at my wife and she is smiling at me.
As Tyler's hands move down my back I notice my wife is now laying on her back and Jessica is massaging her breasts. Lacey starts moaning and says. "You didn't know I like hot women playing with me, did you? I guess there are things we never knew about each other. I like the touch of a woman and you seem to like the touch of a man. Besides you don't suck my tits or lick my pussy as well as a woman can."
Seconds later Tyler's hands were massaging my butt. Next thing I knew he had a couple of fingers inside my ass. Seconds later I came in my panties.
My wife was quick to comment. "Look, Brianna made a mess in her panties. I can tell she can't wait to be fucked in the ass."
"No, I don't want to get fucked in the ass. Watching Jessica suck on your tits and you licking her pussy got me extra excited."
"Don't fight it honey, I love getting fucked in the ass, you will love it too."
"I love it too." Said Jessica.
"I love it also." Tyler added. "The only thing I love more is fucking an ass. Especially a virgin ass like Brianna's."
"I guess I forgot to mention that Tyler is gay." Said Jessica. "Looks like he's got a little crush on Brianna."
"I think we are embarrassing Brianna. He, I mean she's not ready to admit she's a sissy."
"That's fair. Said Tyler. "It took me a long time to admit that I was gay."
Tyler and Jessica finished our massages. I was feeling relaxed and excited at the same time. As me and Lacey got dressed Lacey thanked Jessica and gave her a big kiss. After their tongues met for about 30 seconds Lacey told me to make sure I thanked Tyler. I thanked Tyler and shook his hand.
"No, no, no. Give him a proper kiss."
Before I could say anything Tyler turned to me and planted a kiss on my lips. Without thinking I opened my mouth and let his tongue inside me.
"That's more like it. Lacey said.
As we left the salon the salon Rachel asked how our massages were.
"Amazing."
I walked toward the elevator in the hotel lobby.
"Where are you going?" Asked Lacey.
"I need to change my panties."
"No you don't. You cum in your panties you wear them all day. Every woman knows that. But we do need to freshen up your lipstick. That little make out session with Tyler messed up your makeup."
Before I put on my lipstick Lacey gave me a quick kiss. "Thought you would like to see what Jessica's pussy tasted like." She said.
Everything was happening so quickly I had forgotten I had lunch plans with my daughter and her friends. I quickly put on my lipstick when Amanda called. "Where are you? I am here with Steve and Jack at the restaurant."
"Sorry, I will be right there."
I get to the restaurant. Steve and Jack greet me with a big kiss. I am a little nervous, but for the most part lunch is pleasant. That's until Steve asks about my massage. Amanda quickly jumps in. "I heard Brianna loved her massage so much that she came in her panties when his massause put a finger in his ass."
"Does your mother have to tell you everything?" I asked. I didn't feel like sharing details between her mother and Jessica.
"Only the good stuff, Brianna. You don't need to be embarrassed about cumming in your panties. I cum in my panties all the time. Besides, you sucked Steve and Jack's cocks last night, we are all friends here."
Steve said. "Amanda, your dad looks extra hot today. Love the shiny lipstick."
"I no longer call him my dad. Brianna is my step mom. I love the lipstick also, I just bought it yesterday. If you're lucky I will let you borrow it, then you and Brianna can make out."
"I would love that." Said Steve
"Me too." Added Jack.
Just then, Steve and Jack each take one of my hands and place it on their cocks. They had both unzipped their pants and I could feel their erections thru their underware. Without thinking I began rubbing each cock. I instantly became excited, and I began to rub faster as I felt their pre cum. Seconds later Steve came. He then took my cum drenched fingers and stuck them in my mouth.
Without thinking I started licking all of Steve's cum from his fingers. Was I actually enjoying the taste of cum?
Amanda rushed us through dinner. "We have the Victoria Secret show, I don't want to be late."
We paid the check, and as I left our waiter slipped me a piece of paper with his phone number and a note. "I have a nice cock, I would love to see your hot lips around it."
Amanda and I hurried to the fashion show. We got there with about 5 minutes to spare. She asked me. "What was that paper that the waiter handed you?"
"You don't miss a thing do you? He said he had a nice cock and he left his phone number"
"Are you going to call him?"
"No."
"Why, it would be so wild. He thinks you're a hot woman."
"What happens when he finds out I'm not?"
"Maybe he'll like it more."
Just then the fashion show started. About 15 gorgeous women wearing very sexy lingerie. I finally started feeling better about myself. I was getting turned on seeing attractive women parading past me in sexy bras, panties, and stockings.
After the show some of the models were selling some of the lingerie that had been on display during the show. Amanda walked up to one of the prettiest models and started chatting with her. Soon she had picked out a handful of assorted items, and she called me over.
"Do you like what I bought? Some for me and some for you. I need to borrow your credit card."
When the model ran my credit card thru the machine she gave me a quizzical look.
Amanda chimed in. "This is my step mom Brianna, she started embracing her sissy side a few weeks ago. Isn't she pretty?"
The model introduced herself as Jessica and said. "Yes she is very beautiful, and she is lucky to have such a pretty daughter to help her. I bet many of the men here claiming to buy lingerie for their wives or girlfriends are actually buying for themselves wishing they can look half as good as Brianna."
I thanked her for the compliment. I started feeling better about myself knowing that I was attracted to many of the Victoria Secret models.
Amanda chimed in. "Well, maybe you are bi. You seemed to like some of those hot models. Or maybe you just wished you looked that good in the sexy lingerie they were wearing. Anyway, let's go show mom what we have bought."
We go upstairs to our room. Part of me was excited about trying on my new lingerie for my wife, but as I opened the door, there she was getting fucked by the young life guard she was talking about earlier. I had never seen Lacey so excited.
It took her a few minutes before she realized that me and her daughter were in the room watching. She was moaning so loud she never heard the door open.
"Hi Brianna, hi Amanda. This is Carl. He has the most amazing cock I've ever seen. I have already cum twice. C'mon Carl you must show my husband and my daughter that incredible cock."
Carl pulled his cock out of my wife's pussy. It was huge. He smiled at me and turned to Lacey. "Your husband is a very pretty sissy, look at the way he stares at my cock. I bet he would love to suck on it."
"I bet he would love that cock in his ass." My daughter added. "I know I would."
"Amanda! When did you become such a slut?"
"It's not really fair, everyone is having sex except me. I'm a little frustrated here."
"You are right honey, if it weren't for you noticing your father's sissy potential we wouldn't be here this weekend. Maybe Carl has a friend for you to fuck."
"I'm sure I can find a friend to fuck Amanda."
"What about finding someone to fuck my husband?"
"I think I know just the guy. He loves sissy boys."
I was beginning to get annoyed. "I am not a sissy. I don't want to suck some guy's cock."
"Maybe he's right mom."
"Thank you Amanda."
"Why doesn't Brianna try on the sexy lingerie we bought at the Victoria Secret. If she doesn't get an erection then maybe he's not a sissy."
My wife smiled and winked at Amanda. "That's a great idea. Let's see what you bought."
Lacey ordered me to get naked, then Amanda handed me a matching black bra and panties.
So there I am trying on a bra and panties in front of my wife, daughter, and a young life guard with a big cock. Well, it wasn't long before my cock betrayed me and a had a bulge in my panties.
"Well Carl, it looks like you can call your friend. Come here Brianna let's get you dressed up."
Everything happened rather quickly after that. Lacey and Amanda had me put on sexy thigh high stockings and a very short dress. Hot red lipstick and a blonde wig and I looked like an attractive, but slutty woman.
"Wow." Said Carl "We shouldn't have any trouble finding a date for your sissy husband. Why don't we take some pictures and I will send them to some friends."
While Lacey and Amanda had me pose, Carl took some pictures and sent them to friends.
Within minutes three of his friends texted back. Two of the texts had pictures of big cocks.
Amanda smiles. "My panties are getting wet. I'm the only one that hasn't been fucked this weekend. I want one of those huge cocks"
Lacey said. "Sorry Amanda, tonight is about getting Brianna'a virgin ass fucked."
"Remember, Steve and Jack will pay $2,000 for a virgin sissy ass. We don't want Carl's friends fucking step mom for free."
"Maybe Carl's friends will pay more."
Amanda and Lacey laughed.
To be continued
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