Must Be Dreaming

December 2017 Christmas Dreams Story Contest Entry

Must Be Dreaming

By Jessica C

Eight friends from high school get together for a pre-Christmas gathering...
Saturday the guys were to do their thing and the women theirs...
Josh however gets invited along with the women...

It was three weeks after Black Friday and the guys and women were back together having breakfast, this time near Chicago. They had been friends in high school or some longer and they were together for away weekend from college or work. Most of the guys were pumped up for another weekend of football and pub finding. The women were going shopping for one another and a little self-indulgence as Jennifer phrased it. The gals had paid their breakfast bills and were getting up to leave, when Jennifer turned around and spoke up. “Josh would you like to come with us?”

Dick asked, “Just him, you’re not inviting us?”

Cori said, “I’m glad you understand. Josh relates well with us, you’d ruin the day we have planned.” She and the other women giggle mostly to themselves.

Harry said, “Hey Josh, do you know what kind of man that makes you?”

Josh spoke up, “Lucky and well liked, I’d say.” He knew it wasn’t what Tom, Dick or and Harry were thinking. But his response was accurate. He had been fairly smart in school and graduated when he was barely seventeen. Tom and Harry had the habit of reminding Josh that he was younger.

Tom said to the women, “Girls are you taking him with you so you can train him up the way you like?”

Jennifer spoke saying, “No, we just don’t want you weaken his mind with the same old games of football and beer.”

The women begin to walk away and Josh was happily in the group. Once they’re outside, Ainsley sprays a puff of perfume that he walks into. “Now you’re officially in the club, I hope you don’t mind.”

Josh says, “I appreciate being with you, and the fragrance is subtle. I like it.”


The rest of the morning was spent window shopping and visiting among one another. Now they were stopped at a makeup counter. The cosmetician there a woman named Alexis was well trained and very personable. Jenn, Cori, Ainsley and Meg were all enjoying the time immensely. Alexis turned to Josh, “Oh what beautiful eyes and eyelashes you have. I bet you are teased about having them…” She saw from Josh’s expression that was true, “I dare say you should consider another perspective.” She pauses, realizing Josh is not protesting nor even sadly disagreeing with her.

Alexis says to Josh, “I bet you don’t quite understand the fuss over your eyes. If you’d let me work on your eyes for just a few minutes; you’d understand the remarks you’ve always heard from women.” Josh mumbled, “Even my mother and her friends as well as my grandmothers and girl cousins.

Josh huffs as though annoyed but doesn’t walk away. He looks around and the others aren’t laughing but being quiet. They have subtle smiles that indicate nothing to him. Finally he asks, “If I allow you to do it so I can see what you’re speaking about; will you be able to take it off and help me look normal again?”

Alexis tells Josh, “Most certainly, I wouldn’t expect you to keep the look unless you were pleased with seeing yourself like that.”

Josh confesses, “I’ve heard people saying that since I was four, but all I ever see are my eyelashes that I like but nothing girly. They’re nothing special.” Jenn pats the cosmetic chair that’s there for those to be made over. He sits there with a smile creeping onto his face, hoping a long bedded puzzlement will clear up.

Alexis uses a makeup cloth to make sure the skin around his eyes are clean including natural oils that might interfere. She focuses on Josh’s eyebrows as she waits for his skin to dry naturally. She pulls some stray hairs and does a little shaping, nothing noticeable at least to a guy. She asks, “Would it be okay to use an eye-liner?” Josh says, “Yes, as long as it too will come back off.”

Josh stares ahead not moving his eyes or head, occasionally seeing Jenn or Ainsley off from the corner of his eyes. Ainsley’s expression says she’s pleased. Otherwise neither indicates very much. Alexis uses a dark purplish blue mascara getting both upper and lower eyelashes.

She’s ready to allow Josh to see the end product in a mirror. Jennifer speaks up, “That’s impressive, but if she… he had eye-shadow wouldn’t be more telling.”


Alexis pulls away the mirror, “Josh, I’ve done what you have agreed to. What your friend Jennifer is suggesting might explain why people say your eyes should be on a girl. Would you like to see them now or for me to go a step further?”

Josh says, “If I look now you could still do the eye shadow thing couldn’t you?” He pauses, “I’d like to see them now.” Alexis brings back the mirror and sets it on the counter before Josh. He turns and looks into the mirror and moves his face until he can fully see his face in the mirror. His mouth begins to form the expression ‘Oh’ and his hands come up to cover part of his face but not his eyes.

Jennifer is looking over his shoulder, her hands are warmly there. “Do you like,” she softly asks?

Josh turns to Alexis, “But how could you or others know, I never wore makeup like this?”

Alexis says, “Us women even young teens have come to sense what makeup might help to bring out. Jennifer and the others didn’t need makeup to see the beauty of your eyes.”

Josh turns to Jenn and the others and they’re all agreeing as are a small crowd of women. Jenn and Josh give each other a hug. Jenn being sure their faces don’t mess the look of the other. She whispers, “Would you be open to seeing it with eye shadow?”

Only Alexis knew what she asked, as Josh contemplates, “I’d look foolish if I did that.” Jenn and others in the small crowd that has now gathered shake their heads, ‘no’. Someone softly said, “Just more attractive.” She begins to apologize for speaking up, but says, “You’re already an attractive man. I could enjoy someone like you.”

Josh agrees to allow Alexis to add the eyeshadow. Alexis says something to Ainsley and turned back to Josh. “Thank you for being so cooperative, and you can stop me whenever.” She says, “I’m going to use a little foundation and makeup so the eyes show properly.” She’s soon done, including brushing his hair a little. Josh gets to see the completed look.

A look in the mirror shows an attractive looking college woman looking back. “Josey, you look more like a Josey. I’m going to pack this small shoulder purse with the makeup and things that I’ve used and a little more. They’re all yours for being so accommodating.” Ainsley raises a white satin blouse and a black piece of clothing. He can’t tell as it hangs if it is a skirt or pair of slacks in her hands. Josh is not sure which nor does he care.

Josh says, “I’ve already done enough.”

Ainsley says, “I just was hoping you’d not take off your makeup. The top is kind of a unisex top and it would help you in carrying the purse, but I’d be willing to do that if you’re embarrassed.”

Josh takes hold of the blouse and there’s a camisole to go underneath it, he knows it’s like an undershirt. He looks at it and turns to Jennifer, “Do I dare do it?”

Jenn looking back at him, says, “It’s up to you, but it would be fine with us.” Josh has both the top and the cami, and then looks around. Jenn says, “I’ll show you a changing room.”

Josh turns to Alexis, “What do I owe you for all of this?”

Alexis says, “The makeover is free and I’m giving you the makeup and essential things. There’s well over two hundred in makeup and stuff. You’ll need to pay for the purse and clothing.”

Josh followed Jenn to the changing room and when she says, “The one just around the corner is open. You won’t be bother anyone. Josh felt peculiar, but decided it was one time, and in for a penny, in for a pound. Once changed he notice his shoes missing. Stepping out in in his black socks, he went out to his friends. Cori said, “Try these on your feet.” There’s a pair of black shiny loafers.


It was now one thirty and their small breakfast had worn off. They went to a nice restaurant near the shops they were still interested in looking at. When the hostess said, “This way ladies.” Josh was more at ease with how he looked to others.

While they talked and ate, Megan asked, “Is it alright if we call you Josey for the rest of the trip. During the afternoon and until they finished shopping around six, the focus was on them as women.

Josh/Josey was comfortable watching the others shop, though he was now seeing the same clothes with different eyes. He enjoyed the colors they were looking at and what fit loosely and what would snuggle their figures. He observed at a black skirt wondering if it went with what he was wearing, but said and did nothing.

It was five thirty when the women were shopping for intimate apparel. The women were talking about staying together at the hotel but having nothing special to wear. He thought to himself what they were looking at was not much more than nothing. But he knew they were not looking at things in the same way he was.

Jenn said, “When we get back to the hotel Josey, you can shower and we’ll help take the makeup off. You can then dress in your stuff and get back to the guys for the last of the football games.” Sure enough, when they passed a place with a TV, a football game was just getting ready to start and another game would begin in two and a half hours.

Once in the lobby of the hotel, they went to the lounge and ordered appetizers and some wine. Everyone was enjoying themselves, even Josh, still in Josey persona. It was there Jenn first suggested, “You know Josey, you could complete your experience staying with us for the night.”

Ainsley said, “But remember it’s a women’s time with no sex included.” Josh didn’t need that said. He was enjoying the day and even lost track that he was dressed as Josey. With the exception of keeping Josey’s voice that he needed to be mindful of, less he outed himself. Most of the time he tried even not to talk when others were around.

They visited for another hour exhausting a good list on things to converse about. One including what they thought was important in a man they’d like to have. The choices were: A big pleasing dick and how he performed in bed; his lips and kisses and whether he inspired romantic feelings; his physique and how nice he was to look at or lastly if he had a combination of intelligence and being attractive. Ironically they decided to start this discussion with Josey as she was usually the last to speak up.

Josey thought at first they were kidding about her participation and then Josh protested. Finally Jennifer said, “We’ll order another bottle of wine and let each of us think about it until we’re served.”

While waiting Josey asked, “And how did you come up with the four choices?”

Meg smiled saying, “We’ve each had those experiences; one way or another. You should have an advantage on us getting to be in the locker room and showers with guys.”

Cori says, “And please don’t tell me you guys never look at each other. One guy I went out with was half drunk when he told me most of you did. I didn’t think it was reliable information. But another guy confessed it was true that the locker room and an exciting game makes team members more attractive to some. He clarified it saying he was talking about straight guys not someone who was already known to be gay.”


The wine arrived and was poured into our glasses and a toast was offered. Jenn says, “Now Josey, you’re not getting out of this, so get talking.” But Josey did protest for over five minutes, now finally seven minutes, but it became inevitable that the others weren’t backing away from their persistence. Josey finally said, “Guess it would be in the lips and the inspiring of romance.”

Ainsley said, “Back up, you need to say it would be his lips and kissing and finding him romantic.”

“You wore me down, I’m not worried about the words. His lips and kissing me as well as in sighting romantic feelings between us. There I’ve said it, onto the next person.”

Ainsley asks, “Would it be a young man having strong forceful lips, or a guy with warm, surprisingly soft lips? It is surprising I find a lot of men that the latter. What do you like Josey?”

Without thinking Josey begins talking, “Warm, damp lips, a degree of softness but not mushy. It would be how he felt in my arms and his face to my touch… A passionate kiss probing or caressing my neck and ears. I like doing the same…” Another pause and Josey looked around, “Enough I’m done.” He couldn’t quite remember what he said, but looking around he knew it was more than enough.


The others gave their responses and in more detail than Josey and more in depth the why. Cori actually picked the big strong dick and went into how she wanted a man who was solid to match it. “He has to know how to use it in a pleasing way. No wham, bam, bam, bam, thank you mam. He needs to have a brain that knows how to use it to please me. I want to be able to moan with joy on my way to ecstasy. Don’t all of you like to feel him inside of you, causing erotic pleasure?”

Ainsley agreed with Josey, “He has to be attractive to me, but as an oldies song goes, “It’s in his kiss. I want a nice romantic kiss to begin and end each time we’re together. I don’t want it to be routine, but come from his heart. A good kisser should be able to caress me in many places and ways. I’m not terribly experienced when it comes to sex, but I know good romance when the chemistry is right. Brian was like that in high school. There’s been Logan in college, the results aren’t completely in on him. But then again I’m not ready to settle on a guy.”

Cori quickly begins, “Sorry Jenn and Meg, but I don’t want to be last, and I know what I like. His physique needs to be of a guy in shape, a well sculpted figure of a man. I don’t want a muscle bound guy or someone in love with himself. Most of us like Josh’s body and the fact he runs and works to stay in good condition.”

Others interrupt her at that point, “You weren’t to say that. If it goes to his head you’re in trouble with the rest of us.”

Josh says, “You’re teasing me aren’t you?” The group is shaking their heads no. He never would have guessed. He had dated each one, but friendship seemingly kept it going further into a relationship. Here he was in December of his third year in college, and he could finished his degree next December or earlier. He’d want a master’s degree at least, so it would be two and a half years. It hadn’t been hard keeping his focus because he didn’t think there wasn’t anyone interested in him. Jenn and he both went to universities in Chicago and Ainsley wasn’t that far away in South Bend, Indiana.

Cori went into more detail about the physical side of things she liked in men, but then came the surprise, at least for Josh and Meg. Cori liked having sex with guys, now and then, but she came out about being a lesbian. The knowing smiles of Ainsley and Jenn were there. She talked about one person they knew from high school, but it wasn’t any of them. She mentioned Abby from work, all the women knew Abby to be a woman at least three years her senior and a climber in their company. Abby was an athletic type of woman and attractive in her appearance. Cori made no secret among the group that the attraction was strong and mutual. Seemingly Abby let Cori work in the company for six months before know Cori better. Cori was happy with the company. Abby even encouraged Cori to continue her education by taking night classes to help her reach her potential.

Megan said like Jenn would say, “The man needs a good degree of intelligence and he needs to respect mine. Being attractive doesn’t need to mean what one might think. I could be attracted to a man of a different background. It could actually feed my desire to travel and know different people and places.

“We’d explore ways to enjoy one another. He’d listen and not be put off if I guided him to please me. Like I try to be open to the other person and theirwants. I think it would need to be a man, but I’m not absolutely sure. I’ve enjoyed a couple of times with women but haven’t been drawn to a relationship with either of them.” Josh is surprised as each woman seems to identify with the last statement. “It could be one of us if he could embrace his feminine side more. But no, Josh would be too familiar, I’d want to journey more.” The group talked more exploring ideas that have arisen from the discussions so far.

Jennifer said, “I’d have to choose both the romantic and the intelligence of a person I find to be attractive.” Ainsley and Meg both speak up, “Leave it to Jenn to pick two. …She’d pick ‘the thinker’ if he made it off his ass and could get out of himself.”

“Not true,” said Jenn to Megan, “I had him (the Thinker) and his ability was too philosophical for me. He had trouble imagining possibilities outside of his thinking and I felt he was cold to the bone. I definitely want someone in touch with his feelings and can see the artistic elements of the universe.”

“I see a romantic who is not only intelligent in thought but connects that thought to life. I like being near him; I have met one and we made some beautiful music together. Later however, I found he was already committed to another. I hope I’m not calloused too much that I won’t trust the next one I find.” Cori felt the need to speak and said, “He doesn’t exist.”

Jenn turned to Josey, “Josey do you think he might exist?”

“More than one I’d hope,” Josey sighed, “or poor Josh doesn’t have a chance.”


Josey went up with the women to their suite; where they’d help take of his makeup, then shower and he could get back to the guys. The women had him shower and get refreshed, hopefully looking more like himself. Once dried he wrapped a towel around him and went out to find his clothes. There on the box spring of the bed was his clothes to one side and a short nightgown to the other. A knock on the door, marked the presence of Jenn.

She said, “You know you’re more than welcomed to stay as Josey; we know she’s Josh too. All you need to do is put on the nightgown and the panty and join us. If you do, we want you to stay the night.”

Josh looks and the nightgown is short and the panty can’t be much. “It’s not much and I have more to hide.”

Jenn steps in half way, “That’s what I’m wearing and when you sit around the circle. You’ll see we’re not hiding much at all. She steps in nearer to Josh, and lifts a small bottle of spray perfume. A light mist flies in the air, “We would love you to stay.” She turns around and goes back to the main room, glancing back once as she steps through the door.

Josh selected what he’d wear and then brushed out his hair. Josey stepped out into the suite finding four mattresses had been pulled out and placed together. There were pillows from the beds and pillows from the furniture forming a circle on the mattresses. The only one whom you could not see through their panty was Josey. They had left two panty liners with instructions for Josey. Josey would close out the night and see it to the morning as a woman. It was hours later that each of the five would drift off to sleep.


Josh fell asleep only after he was kissed numerous times by Jennifer.

He woke up in the morning being sure he had a recurring dream. He had them before more than once with each of Ainsley and Jennifer. The only difference this time; it was the first time all four women were in his dream at the same time and he had spent the day together with them. The first time his girl image was named Josey. When he awoke, he was saddened, it was just a dream…

He stretched to wake up and rolled to the edge of the mattress, so his feet could find the floor. As his feet hit the floor much too early in their decent, an arm and hand touched him. It was Jennifer, she was lifting herself up on an elbow, “I have a question for you? I had a dream, hoping you Josh and you Josey could be my Christmas dream come true?”

Jennifer and Josey were quickly making love as Cori, Ainsley and Megan threw sheets and bedspreads over them. No complaints or taunts to stop. Jennifer and Josey say sweet nothings and moaned, finally Josey answered for her and Josh…

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