Pretend Girlfriend

Warning - this contains non-con/reluctant sex.

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I suppose I should know better. Sometimes when you try to help someone it blows up in the worst possible way. I'm Kelly, 23 years old and in spite of my name was male. I did contract work, often remotely and was now making a decent living. I had a best friend, Kurt who I'd known since college. We'd hung together for years.

Kurt was a total loss when it came to women. Not only did he get tongue tied around them, when he spoke, he had a tendency to say the worst possible thing. I'd tried setting him up on blind dates a couple of times before I gave up. He was so bad his dates disappeared long before the date was supposed to be over. When I talked to the women, they told me never to set them up on a date ever again. They also told me never to set Kurt up on a date with anyone ever again.

We still were friends, and particularly when we were younger he had helped me out of a pinch several times. I felt like I owed him, so when he came to me asking me to help him, I of course said 'yes'. Little did I know what helping him would entail. Even though everything worked out at the end, it was pretty shitty along the way.

"Kelly, bro, I need a favor."

"Anything for you, man. You know that."

"This is a really big one, Kel."

"So hit me with it."

"I have a problem."

"Why the hell else would you be asking me for help, Kurt?

"You know my track record with girls."

"Kurt, none of the girls I know are willing to go out with you."

"My folks have been bugging me about having a girlfriend."

"If a girl won't go out with you a second time, how the hell are you going to get a girlfriend?

"I lied to them and told them I had one."

"Tell them she broke up with you, maybe."

"They want me to come home for the holidays and bring my girlfriend with me."

"How the hell are you going to do that, Kurt?"

"That's why I need your help."

" If I can't get a girl to go out with you, then I sure as hell can't get one to spend a week pretending to be your girlfriend."

"Kelly, I need you to pretend to be my girlfriend."

"They're never going to believe I'm a girl."

"They will if you take one of those sex change pills."

"You want me to change to become a girl, then meet your parents pretending to be your girlfriend?"

"Exactly."

"You got to be shitting me."

"Kelly, it's only for a week."

"A week? You want me to do this for an entire fucking week?"

"You owe me, and you said you'd do anything I needed."

"I didn't think you meant something like this, dude."

"Come on. It's not going to be that bad, Kelly."

"Easy for you to say. You're not the one becoming a girl and pretending to be someone's girlfriend for a week."

"Do this and we're even for everything. I won't ask you for another favor as long as we live."

"You know I fucking hate you, Kurt."

"You have a week to get ready."

"I need to get a women's wardrobe."

"So do it. You have time."

"My body won't be the same shape. How do I get clothes to fit?"

"I have a pill that lasts a week. I'll give it to you a couple days early so you can shop."

We were supposed to fly out on Monday, so I took the pill early Saturday. I'd talked with Terri, who I'd been casually dating. We were not exclusively dating, but we liked each other. I told her what I was supposed to do and she said she'd help me get some clothes. She came over right after I'd taken the pill and told me to strip, so she could get an idea as to my sizes.

My clothes obviously didn't fit so well anymore, but I put on briefs, jeans, and a loose tee to go shopping. The first place she took me was a store that specialized in intimate apparel. She seemed to take great pleasure in picking out some of the sexiest bras and panties and telling me I should buy them. I was at a loss as to what sizes I needed and though it pained me, bought what she suggested.

She said I needed sleep wear, unless I was planning on sleeping in the nude, which of course, I wasn't. She tried to push me into a sheer and skimpy negligee. Instead, I selected two sleep shirts that were far more modest. I wasn't sure what our sleeping arrangements were to be, but I sure didn't want what she seemed to be pushing.

Kurt's family lived in Florida which was warm even now and he'd said they had a pool. Terri tried to push me into getting the smallest thong bikini that I'd ever seen. Mercifully a clerk came along and helped me find a far more modest two piece suit. I'd have preferred a substantial one piece, but the clerk and Terri convinced me to get a two piece.

We went from there to another store, where I headed straight for jeans. Terri helped me select a couple pair, but also told me I needed dressier slacks as well as skirts or dresses. I pushed back hard on the idea of a dress, but she convinced me I at least needed a nice skirt for dressier attire. Of course I had to try these things on and model them for Terri.

I wanted to go for more casual tops in more muted colors, but she told me I needed a dressier top. She sent me back to try on very low cut top which all but blatantly showed my boobs. I hated having breasts, and certainly didn't want to go showing them to people. We compromised on one that wasn't quite so low cut.

Next of course was shoes. I just wanted to wear my running shoes, but she said that at the very least I needed a few pair of flats. We selected a few pair of those, then she wanted me to get heels, since she said every woman our age, even the ones who weren't particularly stylish, had some heels. I couldn't even walk in the high heels, so we got some lower, wider heels for me.

I assumed we were done, but Terri assured me we still had quite a way to go. She took me to a salon, where she had my hair cut and styled. You can imagine how much I loved that. What I loved even les was when she took me to get a mani-pedi. After some lengthy negotiations, we agreed on a muted color on my finger nails and toe nails.

We still were not done and she took me to buy cosmetics. I never realized quite how much stuff women put on their face. By the time we were done I had a full supply along with face, hand, and body lotions. She also had them do my face and explain the items and techniques. Terri had me go in a bathroom to change after our earlier purchases and I could hardly believe how I looked.

Next stop was a jewelry kiosk, where she had me buy some bangle bracelets and simple necklaces. To add insult to the injuries I'd already suffered, she had them pierce my ears and had me buy several pair of earrings. By that time, I was almost in shock, but the shock was redoubled because Terri had called Kurt, telling him where we were.

"Hot damn, Kelly. I'm going to have the sexiest girlfriend in town."

"Kurt, just shut the fuck up."

Terri piped up. "So, Kurt, you approve of my makeover?"

"Shit, I just wish Kelly could stay this way."

"Bitch, first I don't plan on doing that, but even if I did, it sure as hell wouldn't be as your girlfriend."

Kurt had a snide grin. "Oh is it her time of the month already?"

"I'll 'her time of the month' you upside the head."

Kurt looked me up and down a couple of times before having a shit-eating grin. "I am really going to enjoy next week."

"One fucking week -- not one second more, Kurt."

"You realize we will be there for a week, and you took that pill two days early to buy clothes."

"So get one to cover the difference."

"Kelly, the short ones are 24 hour, 48 hour, and seven days, and given when this runs out and when we leave, the 48 hour might not cover it."

"Regardless of when the pills run out, once we leave there, I no longer have to pretend to be your girlfriend."

"Spoil sport."

"Don't push it, asshole, unless you want me to back out."

"You promised to do this and you've already taken the pill."

"You used to be a friend."

"I'm sorry, Kelly. I'll quit pulling your chain."

"I'm getting a better idea about why all those girls dumped you."

Terri stood to one side, watching this exchange and grinning. At least she didn't laugh out loud, though I know she must have wanted to. Some people walked by us in the mall and glanced over, though they kept going. I suppose we just looked like a couple who were arguing. We were not a couple, even if I'd have to pretend we were for a week.

I never regretted a promise half as much as the one I made to Kurt. I stood there glaring at Kurt, until Terri suggested that Kurt apologize by taking us to dinner. At that point, I didn't want to spend one additional second with Kurt, but as Terri pointed out, I'd have to spend a week pretending to be his girlfriend, so I needed to get over it.

Kurt took the three of us to dinner and the food was decent. Given that Kurt was with two women, assuming you considered me one, he was as big an ass as he was on any of his dates. Between Terri and I, we read him the riot act and told him he'd have to clean up his behavior or else. For my part, I told him that if he didn't treat me with respect as a girlfriend, I'd walk out on him, regardless of my promise.

That made him subdue his behavior somewhat. Kurt may never be anything but an ass when it comes to women, but he may at least be less vocal about it. In truth, I guess being a guy -- until that damned pill -- I'd been insulated from most of it. I guess he was still something of a jerk, but it was not as bad and I was free to call him on it.

In one sense, I was still free to call him on his bad behavior. Most of the time, around his family, I figured I'd do it more discretely. With me, Kurt, and Terri in the restaurant, we both did it far more openly. By the end of the meal, Kurt was somewhat more subdued. I figured I'd try to keep him subdued for as much of the time as I could.

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The next day, Terri spent a lot of time working with me so I could do my hair and makeup passably. My first few attempts scared even me when I looked in the mirror. By the end of the day, I looked okay, though hardly spectacular. Terri helped me pack my clothes, which I appreciated. Honestly, even though I was now a woman, I'd have loved to share some intimacies with Terri.

She made it clear, she was only into guys, but said once I changed back, that we could have some fun again. In the meantime, I had one long and no doubt painful week ahead of me. Even if I could get my idiot friend to act better, it was likely to be difficult. I slept fitfully Sunday night, knowing I had a flight followed by a week pretending to be Kurt's girlfriend.

In the morning, I wore a sports bra, jeans, a comfortable tee, and my running shoes. Traveling is difficult enough without making it harder by dressing uncomfortably. Kurt offered to pick me up, but I told him that I'd meet him at the airport. I took a ride share, so I didn't have to pay for a week of parking. The damn clothes had set me back more than enough already.

He'd given me the information so I'd checked in remotely and downloaded my boarding pass to my phone. I went to the airside and waited by the gate with my carryon bag. A little later Kurt showed up, and acted like I really was his girlfriend. I told him to cool it -- while we might have to do that around his family, I didn't intend to play that game before I had to.

"Don't you think we need to practice some before we get there?"

"We'll have plenty of time to practice this coming week, and that's more than enough."

"We have to make them really believe it."

"If you can act like something other than a jackass, I can act like your girlfriend."

"I was hoping we could have some fun, Kelly."

"Pretending to be your girlfriend is not fun for me."

"I didn't realize that turning you into a girl, would turn you into a bitch."

"I don't like being a woman and don't like pretending to be your girlfriend. I'm only doing this because we've been such good friends."

Kurt sat beside me and pouted until it was time to board. Kurt had booked and paid for the tickets and when he did got us seats together. I suppose that made sense, but I was still uptight about the whole thing. When we boarded, he wanted to put up the armrest between us and I wouldn't let him. I get it -- he wanted to enjoy the idea of having a girlfriend -- even a pretend one.

When the plane landed, I took a deep breath. As soon as we were off the plane, I had to act like I really was Kurt's girlfriend. Someone from his family was going to pick us up, and I had no doubt they'd be there as soon as we were off the plane. As soon as we approached the exit, I took Kurt's arm, as though I really liked him.

Okay, we were close friends, so I liked him as a friend. That didn't mean the same thing as we would pretend it did. Kurt had a big grin as we exited the plane, and once we were back in the main terminal, we were met by half a dozen of his relatives. Both of his parents were there, along with his brother and sister, and one set of grandparents.

We had hugs all around, with the whole family wanting to hug me. Once we finished the greetings and introductions, several of them looked me over very carefully. I suppose they knew what a bozo he was and wanted to know how he landed a cute girlfriend. Perhaps oddly, I think his sister Rebecca paid the most attention to me.

His father was the first to comment. "Damn, son, how in hell did you manage to land someone like this pretty lady?"

"It was my great personality."

I couldn't help but roll my eyes for a second before recovering and giving a demure smile. I could tell that Rebecca had caught that, and she had a stupid grin. Kurt's brother Michael slapped Kurt on the back and told him he didn't think Kurt had it in him. Kurt said he had it in me, as well. I gritted my teeth and elbowed him in the ribs, which made Rebecca laugh out loud.

Rebecca had to comment. "Well, Kurt, I see you haven't changed that much."

I gave a sweet smile before commenting. "I'm still trying to housebreak him."

"You clearly have a lot more work to do."

Kurt looked a little peeved, at least until I rubbed my head up against his. He reacted by swinging me around, hugging me and giving me a passionate kiss. Since I was supposed to be his girlfriend, I had to let him and respond to his kiss. As soon as he broke the kiss, I bopped him on the nose with my finger and told him that we agreed no public displays of affection.

Kurt pouted a bit, then the eight of us proceeded to the cars. Given the number of folks, there were two cars. Kurt, of course wanted to sit with me, but Rebecca told him he'd have plenty of time with me over the next week, and she wanted to get to know me better. Kurt and I had talked and worked out our little back story so we wouldn't get tripped up if questioned separately.

Of course Rebecca wanted to know how I met Kurt, how long we'd been dating, where I thought the relationship was going -- all that kind of stuff.

"You know my folks would love to see Kurt married and starting a family."

"Neither one of those are happening any time soon -- not with me anyhow."

"Are you in love with him?"

"No, definitely not."

"Kurt seemed to tell my folks that the two of you were getting serious."

"I am not ready for marriage, and not having any kids any time soon."

The grandparents were in the front seats, and grandma said she felt like Kurt's parents would push him to propose to me.

"I sure hope not, because I'd have to say 'no'."

"Emily will be so disappointed."

Emily was Kurt's mother and I guess it was her pressure that caused Kurt to lie and tell them he had a girlfriend. Rebecca and I talked and I found that she and I liked a lot of the same things. Honestly, I'd have preferred being Rebecca's boyfriend to being Kurt's girlfriend, but that wasn't very damned likely. I did enjoy it though.

I was feeling pretty good, when Rebecca told me that her parents expected me to share a bed with Kurt. Now I'd far prefer sharing a bed with Rebecca but that clearly wasn't going to happen. Now I was really glad that I had the long sleep shirts instead of the almost transparent negligee that Terri was pushing me to buy. I sure as shit didn't want to wear something sexy if I was sharing a bed with Kurt.

God knows it was going to be dicey enough just sleeping beside Kurt in bed. He knew this was pretend and that I was a guy in a woman's body. I wasn't sure that he wouldn't take sleeping together as permission for something more. I suppose that was why Kurt's mother had us sleeping together. She wanted Kurt married and his wife having babies.

I was not going to marry Kurt and certainly not going to have his babies. Call me paranoid, but after I took the pill, I had an IUD put in. I didn't trust Kurt even if he knew that wasn't what I wanted. The doctor told me that when I changed back, as my penis and testes dropped, it would push out the IUD, so I had no particular worries.

We got to his parents' house and I wheeled my rolling bag in. They showed me to the bedroom I'd be sharing with Kurt. He and I got in there and I shut the door. I tried to keep my voice low as I spoke.

"Look, Kurt, we're sharing a bedroom, but that doesn't mean -- "

"You're my girlfriend, aren't you?"

"I'm your pretend girlfriend and the pretence is only when we're with your family."

"You're in my family's home and they're around all the time."

"They aren't around when we're in the bedroom with the door shut."

"Don't be that way, baby."

"I'm not your fucking 'baby', I'm putting on a show to keep you from being embarrassed in front of your family."

"Just calm down, Kelly."

"Keep in mind, I'm a guy who took a pill to be a girl for a week because we couldn't get a real girl to do this."

"And I appreciate it."

"So for God's sake don't push the envelope."

"It's just -- I've never had a girlfriend before and I want to enjoy the whole experience."

"Enjoy it when we're in a room with your family and back off when it's just you and me behind closed doors."

"I'll try -- it's just -- I wish you really were my girlfriend."

"If you didn't run off every girl you went on a date with, you might have a real girlfriend instead of just a pretend one."

"You really are wonderful for doing this."

"And the best way to thank me is to not make me sorry I agreed to do this."

"Believe me -- I've got it."

About that time, there was a knock at the door, and we heard Emily, Kurt's mother. "Okay you love birds, it's time for dinner so leave the lovey-dovey stuff for later."

I mumbled as we headed to the door. "Like I want any lovey-dovey shit."

"Now, now,baby."

"I'll 'baby' you right in he teeth."

I glared at Kurt, then plastered a smile on my face as he opened the door. We went down to dinner and I played the girlfriend, and tried to be sweet and encouraging to Kurt. He didn't act like quite so much a jackass as normal. The food was tasty and plentiful and the family seemed happy to have Kurt home and particularly happy that he seemed to have a girlfriend.

Emily piped up first. "Kelly, so when are you two going to get married?"

"I've told Kurt that I'm not nearly ready for marriage."

"Neither of you are getting any younger."

"I'm in no hurry to settle down."

"Don't wait too long to have children."

"Not every woman wants kids."

"Some women say that when they're younger then are unhappy when they get older and can't have any."

"I'll take my chances."

"I want grandchildren, and neither of these two seem in any hurry to give me any." Emily cast a disapproving glance at Rebecca and Michael.

"Don't pin your hopes on me."

Emily huffed, and I noticed that Rebecca was trying valiantly not to smile or laugh. Michael scowled and shook his head. It was clear that Kurt's father, Andrew had heard Emily pushing various kids to get married and have children. Kurt's grandparents had heard Rebecca and I talking earlier and seemed bemused by it all.