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Chris woke and stretched, memories of last night still swimming in his mind as he went to the bathroom to get cleaned up. His breasts were still held in place and were not showing any signs of peeling off. The literature wasn’t kidding when they said you could sleep in them with no problem. Thought he would have to reapply them before they went out tonight, the stuff was only good for 24 hours. The last thing he wanted was a boob falling off while they were having whatever fun Dave and John had planned. Taking off his wig he washed up and got ready for the day.
He decided to go with minimal makeup again after shaving. He was convinced after seeing the video and pictures last night the John wasn’t kidding that he could pull it off without a lot of caked on makeup. He just needed to make sure he shaved really well this weekend. He thought when he got back home, he’d have to look into laser hair removal so he wouldn’t have to shave any more. He picked out a button-down shirt that accentuated his breasts. He’d have to get some shirts cut for a woman so he wasn’t wearing his regular shirts all the time when he was dressed as a woman. He wondered if he could pull off some tight-fitting jeans too as he slipped on the pair of jeans he was wearing yesterday.
After taking a look at himself in the mirror he didn’t like it all. He decided that he needed to do some shopping today. If he wanted to pull this off, he needed actual women’s clothes. So, he stripped off his clothes and pulled on another dress that he’d packed. This one was a tight-fitting mini dress that barely covered his ass. Luckily, he’d shaved so he didn’t need any hose so he slipped into his heels and took a look in the mirror. He liked what he saw but dressed like this, early in the morning. It looked like he was doing the walk of shame. He giggled at the thought. There was no shame in what happened last night though. He loved every minute of it. Tossing some things into his clutch he grabbed his phone and was going to text John when he saw he had a few texts already. Looking at them he saw they were from Christy. Apparently, she saw the pictures and video. “Oh my God baby! Call me as soon as you can. That was so hot!” and it had a bunch of fire and heart emojis at the end. He laughed as he dialed Christy’s cell number.
She picked up on the second ring. “HI baby! Oh my God you looked so hot last night getting it from both ends dolled up like you were. Watching those tits swinging along with your cock got me all wet. I just rubbed one out.”
Chris laughed. “You like me with a pair of tits all dressed up?” He probed.
Silence for a moment on the other end, then she responded. “Yes. You looked so good. I also saw that you were wearing a little less makeup.”
Chris let out a little sigh. She actually got so hot that she got off on it, he thought. He wondered what else she was thinking. “Well, they both said I didn’t need much with my face having a bit of a feminine look. So, for the second go around I didn’t put on a lot. They both loved it. Though I think If I continue to do this, I need some laser hair removal. Shaving all the time is a pain.”
Without missing a beat Christy responded enthusiastically. “That would be good. Besides. I like you all smooth. So, did they tell you what I wanted them to do with you for the weekend?”
Chris let out a low moan. “Yes. You little devil.”
“And are you doing it?” She asked with a stern tone of voice.
“Of course. I still have on the breast forms form last night and I’m all done up. You think I’d pass up a chance at this?” He replied. “Want to see?”
Chris started a video call with her and she picked up. When the video popped up, she was sitting on the couch in nothing but her robe, which was untied, hanging loose, showing off her belly and tits, her legs crossed under her on the cushions. “Mmmm, nice look. Do you intend to stay like that all day? I’m missing out.” He quipped.
Christy laughed. “No. I have some shopping to do. Then I’m not sure what I’ll be up to. No good for sure.” She flashed him a wicked grin. “And what about you? You look awfully dressed up for a day out.”
“Well, I’m thinking I can convince John and Dave to take me shopping for some more feminine jeans and shirts that are a bit more casual. My jeans and shirts I have with me just don’t convey feminine.” He chuckled. “I think the promise of more blow jobs will get them to go along.”
Christy laughed. “You little slut.”
“And you love it.” Chris turned and rubbed his ass for the camera.
“Oh yes I do.” She was rubbing her stomach and chest in response and then stopped. “You know what? I think I know what I’ll do today.” A wicked grin crossed her face. “And I think you’ll agree that it’s a wild idea.
Chris stopped and smiled at her. He wondered what she had in mind. “More fooling around online? And how did it go by the way?”
“Oh, it was fantastic.” She sighed. “But I’ll tell you all about it when you get home. Suffice to say, I showed off for a girl and then a guy last night. They got quite internet casino a show, and so did I. I came three times.”
“So, then what do you have in mind?” He asked as he fixed his makeup up. He would have loved to be there watching Christy use her new toys and getting off in the chat rooms but He’d have to wait until he got home to hear all about it. She was such a tease.
“Remember a few months ago when we picked up Tom and his friend on your first night out all dressed up? But his friend wasn’t interested in the kind of party that we were going to have?”
“Oh yeah. But you came on to him and offered to sleep with him if he ever wanted to.”
“Yes. I’m going to give him a call. See if he wants to have a little fun tonight.” She paused a moment and looked thoughtful and then spoke again. “So that brings me to my next suggestion. I know we said we’d never bring anyone home to our house but I think this case is a bit different.”
Chris knew what she was going to say and he was okay with it. They’d all talked and hit it off so it wasn’t like she was inviting a complete stranger into their house. Before she could say anything, Chris spoke. “I’m fine with that. We both know him. Are you going to have him spend the night?” Chris raised an eyebrow at her over the phone. He didn’t mind. He was planning on sleeping with John and Dave tonight.
“That’s an even better idea. I need someone to keep me company in bed while you’re gone.” She flashed him a wicked grin. “But just for tonight. I’m sure he won’t mind. Did you sleep with your new loves last night?”
“No. They went back to their hotel rooms. I was incredibly tired after the conference and a night of fucking. And I wanted to see how these breast forms held up sleeping. I didn’t want the illusion to be ruined for them. They are, however, staying in the same hotel as me. I think I’ll have them stay with me tonight.”
“Oh?” She cocked her eye. “And how did they do?”
“They did fine.” Chris replied as he caressed his breasts. “I even took a shower with them this morning and they stayed in place. I’ll have to reapply them before we go out tonight. I don’t want a boob popping off while we are playing around or out and about later.”
They both giggled at the thought.
“Enjoying your weekend as Lisa than?”
Chris groaned. “So far yes. I have to admit, taking a shower this morning with these on was a turn on. “I was actually wishing they were real so I could feel my hands on them.” He smiled at the camera and blushed. He wasn’t sure why, but he did. Was it that he was admitting, in a way, that he wanted a real pair of breasts? Or was it just a passing thought and he was caught up in the moment?
Christy smiled at him and rubbed her breasts in response. “You’d like a pair of these?’ She teased. Chris was surprised she didn’t seem taken aback at his admission and seemed to want to probe more. “You are naughty.”
Chris rubbed his chest with his hands for her and Christy moaned. She was really getting into it. “You know how naughty I am.” Playing up his female persona, he blew a kiss at the camera and squeezed his breasts together and let them fall, bouncing on his chest. “If I had tits, I’d probably never leave the house. I’d be too busy playing with them all the time.” He laughed and continued to get ready to go, wondering if Christy was being serious.
Christy laughed too. “I wouldn’t doubt it. But right now, you better stop playing with yourself and get out there. I’m sure your two boyfriends are waiting for you. What are their names anyway?”
“Dave and John.” Chris replied as he touched up what little makeup he had on. “Well, Have fun today, and tonight.” He grinned at her through the camera. “Don’t wear him out. I’m off to do some shopping and then we’ll see how the rest of the day and night unfolds.”
Christy stopped caressing her breasts and smiled. “You too, Lisa.” Treat your two men nice. And send more hot pics. Bye baby.” She blew a kiss at him and hung up before Chris could respond.
His mind raced with possibilities of what they just discussed, in a roundabout way. Did she really want him to get implants? Did she want to take it that far? Was he really willing to take it that far? He wasn’t totally sold on the idea but it did nag at him when he was dressed up. He enjoyed it quite a bit and was really getting into being dressed a s woman. He’d think long and hard about this, but right now he needed to get going. Looking at his watch, it read 10:00, and looked way to masculine on his wrist. One more thing for him to change he thought.
Heading out the door, he texted John to see where they were at. He figured he’d head down to the buffet for breakfast and mee them there. On the ride down the elevator, he got a response.
“We’re eating breakfast. Come join us at the buffet.” John’s text read.
“Headed that way now.” He typed back.
Walking through the lobby to the buffet garnered him a few looks. Some approving and others were a sideways glance with a chuckle. He knew now that he was convincing canlı poker oyna enough to pass as a woman so he figured those chuckles were people thinking the same thing he had earlier, the walk of shame. Never mind them though. He had better things to think about. Reaching the buffet, he was Dave waiting for him at the entrance.
“Hi Lisa.” Dave greeted him and eyed Chris up and down, taking in his long legs and tight red dress. “We’re sitting at the back so I came up to greet you.”
Chris smiled at him as he saw Dave checking him out. “Thanks. So, did you two sleep well last night? I hope you’re up for a fun day.”
Dave chuckled. “Yes, I did. John did too. Let’s stop and get something from the buffet before we head to the table.” He said as they wound their way to the food.
“Wonderful idea.” Chris gushed. “I’m hungry. You two wore me out last night.”
Dave smiled and suppressed a laugh as they filled their plates with food. “It was incredible. Thanks for a memorable experience.”
“Well, it’s not over yet. We’ve got all weekend. That is, if you want to.” Chris said as they worked through the tables to where John was sitting.
“Of course.” Came Dave’s enthusiastic reply as he sat down. “I don’t want the fun to end yet. Right John?”
“God no.” John said as his two companions sat down. “Last night as great and I want the fun to continue.” He smiled at Chris. “A little dressed up for a day out aren’t you, Lisa?” He asked as they all began to eat.
“Well.” Chris blushed, “I hadn’t planned on this turn of events.” He leaned in closer. “I don’t have anything to wear that isn’t a dress or club wear.” He glanced at John and Dave. “Would you two mind taking me shopping? We could head to the mall to get me a new watch, some jeans and shirts, and some new shoes that aren’t dress shoes.”
John looked at Chris and smiled. “Sure Lisa. We can do that.” He sat back and glanced at Dave. “Don’t you think so Dave? Take Lisa out for a shopping spree?”
Dave agreed wholeheartedly. “Sounds good to me. She needs the right clothes for the situation. And it will be our treat.”
Chris gasped. “You mean it? You guys will pay for some new clothes for me?”
“It’s the least we can do for the good time you are showing us.” Dave said as he smiled at Chris.
Chis blushed a bit. “Well thank you guys. I’ll be sure to give you a great time the rest of the weekend.” He leaned in closer and whispered. “Maybe I could start off thanking the two of you with a quick blowjob in one of your rooms. After all. Didn’t my wife tell you two to take good care of her hooker?”
He leaned back and grinned at the two of them.
A low moan escaped Dave’s lips. “That sounds like a great idea. What do you say John?”
John was grinning and getting up from the table. “Well, that’s a no brainer. Let’s go.” He was in the lead ats they worked their way to the elevator.
Dave and Chris were not far behind. As they walked through the lobby Dave put his arm around Chris’ waist and he moved in closer as if it was the most natural thing in the world. He was getting more used to walking around all dressed up with confidence. Last night had been a real boost to his capabilities and he was slipping right into his persona easily and very comfortable with it. Catching up to John, Chris slipped an arm around John’s waist and kissed him on the cheek. The elevator finally got there and disgorged the group of people getting off. Stepping on, the doors closed and left them alone. They were the only ones on the elevator.
Chris leaned in and kissed John deeply. “Thank you. You two are being so nice to me.”
He turned and kissed Dave too, sliding his tongue into his mouth and rubbing his groin as they rode up to their floor. When they got off on their floor, they ran into a group of six guys getting on the elevator. Both John and Dave said “hi” to them as the group parted to let them through. Some of them took an appreciative glance at Chris as the passed by.
“Who were they?” Chris inquired as they reached John’s room.
“Coworkers here with us for the conference.” Dave replied as they entered the room.
Chris noticed a door connecting the room next to John’s was open. “Is that your room next door then Dave?”
“It is. We figured with what we had planned for the weekend, having adjoining rooms would be better.” He was dropping his jeans as he talked, ready for Chris to suck him. “No one in the office knows that we are fooling around with each other, or that we are bi.”
“Awfully presumptuous of you, Dave.” Chris said, as he glanced down at the bulge in Dave’s underwear.
“Well, you did say you wanted to give us blowjobs Lisa.” He grinned.
Chris giggled. “Yes, I did.” A hooker should abide by what she agreed to.” He giggled and both men gave a small chuckle. He reached over and rubbed the large bulge in Dave’s underwear and glanced at John, who was now getting out of his clothes. Chris walked deeper into the room and got on his knees, ready for the two gentlemen.
“Well let’s get down to some poker oyna fun then.” He grinned up at them as they eagerly came forward, cocks now hanging out and ready to go. He licked his lips as he gripped both of them in his hands and began stroking them to full hardness. Save pumped his hips back and forth and John did the same. Chris fell into a rhythm with his hands, stroking both men at the same time, their balls swaying with every stroke.
“Mmmmm. Who should I suck first?” Chris cooed as he looked up from his position on the floor. Glancing back and forth he leaned in to Dave’s cock and swallowed it in one move.
Dave watched as Chris greedily gobbled down his cock. Groans escaped his lips. “Ahhhh. God Lisa, your mouth feels incredible.” Dave moaned and groaned as he kept pumping his hips in time with Chris’ bobbing head. His face contorted with pleasure as his thrust in and out of Chris’ red lips. Muscles in his legs tensed as waves of pleasure washed over him. Just when it looked like he was going to cum, Chris pulled off him and he moaned in protest. “Don’t stop baby.” He pleaded as Chris began stroking the spit slick cock in his hand.
“You wouldn’t want me to ignore John now, would you?” Chris sighed as he batted his eyes at Dave before turning to John and doing the same to his cock.
John was in awe at how well Chris switched between their cocks. He turned, opened his mouth, and took the length of his cock easily. “So hot Lisa!” John moaned. He held still as Chris bobbed back and forth on his cock. John groaned as Chris pulled his mouth to the tip of his cockhead and then swallowed him again, mouth sucking hard and tongue sliding over his hard shaft. “Ughhhh. Mmmm. Suck a good cocksucker.”
“You know it.” Chris moaned as he pulled off John and returned to sucking Dave. Back and forth he went between the two men. Alternating sucking and stroking them. He would suck one cock for two or three strokes and then turn to take the other cock in his mouth while stroking the other. Eventually he pulled off both cocks and tugged them, urging both men to move closer. They each stepped in close and their cocks now touched each other. Both men moaned as Chris rubbed their cockheads together. He then leaned in and began licking back and forth moving from one cockhead to the other, occasionally slipping his tongue between them.
“Oh my God Lisa. That is incredible.” John moaned.
“Yessss. Dave grunted. “Your tongue and John’s cock pressing against mine is so good.” He tensed up and sighed, “I don’t think I can hold out much longer.”
Chris continued stroking and licking both cocks, his tongue running up and down the heads and shafts of both men. “Do it. Cum for me. Both of you.”
John let out a long low moan as Chris knelt there and begged for a face full of cum. He tensed up and cried out, “Oh God, I’m going to cum.” He thrust his hips forward and exploded just as Chris pointed his cock at his open mouth. He watched and moaned as his cock exploded, sending stream after stream of cum into his open mouth and on his face. He watched in awe as shot after shot flew from his cock and landed on Chris’ face and mouth as he knelt there, not attempting to close his mouth and swallow. Just as he was coming down from his orgasm, Dave grunted and called out he was going to explode.
“Dear God that is incredible” Dave groaned as he watched john explode on Chris’ face and mouth. “He tensed up as John finished cumming and called out, “Oh God Lisa, get ready for it! Here it comes!”
Chris looked over at Dave in time for the first shot of cum to land in his mouth. He held his face in front of the spasming cock and let it shoot it’s full load directly into his mouth. Between the two of them he was getting quite the mouthful as his cheeks filled with the warm sticky fluid. After a few more shots Dave sighed and his cock stopped shooting cum. Chris’ face had streaks of cum on it and his mouth was wide open and full. He grinned up at the two gentlemen, closed his lips, and swallowed the huge load in his mouth. He finished by licking his lips and wiping the rest of his face and cleaning his fingers, sucking each digit like it was a cock itself. “That was a great way to start the morning before heading out.” He exclaimed.
Both Dave and John were watching in rapt attention as Chris stood up and pulled his dress back on.
“That was incredible.” Dave stammered. “I’ve never seen anything like that Lisa.”
“You must not watch a lot of porn then.” Chris replied with a smile on his face as he leaned in and planted a kiss on Dave. He was sure the taste of cum was still on his lips as he thrust his tongue into Dave’s mouth. Dave responded by returning the favor, thrusting his tongue deep in Chris’ mouth and wrestling with him. Breaking the lip lock Chris excused himself. “Pardon me boys, but I need to freshen up.” Chris grabbed his clutch and disappeared into the bathroom to clean up. He washed up his face and cleaned up his neck before slipping his dress back on, all the while thinking about what to look for today while shopping. He figured he’d need a couple of pairs of jeans, a couple of shirts, and some more sensible shoes to walk around in, maybe a pair of tennis shoes that looked more feminine. He freshened up his makeup and was ready to go out shopping now.