Three Days as a MILF

As I was pulling into my driveway from a long day of running my startup company, I saw her again. My beautiful 37 year old MILF neighbor Jessica with her blue eyes and medium length dirty blonde hair. She was on her front lawn wearing a flowery blouse with mom jeans completely bent over, planting some petunias. God. She had the widest and plumpest ass I'd ever seen. Most of my friends prefer round and perky asses on much younger women. But me? I'm obsessed with her double wide mom booty. I would do almost anything to be able to grab two big handfuls of it.

As I parked and started walking to my front door I tried my hardest not to stare so I wouldn't be caught. As I was inserting my key into my front door I heard her from across the lawn.

"Howdy neighbor, coming back from huh?" she said walking towards me.

"Yup, just getting back after a very long day, I can't complain though the pay is good." I said shrugging.

"Well that's good to hear. Do you mind if I come in?" she said with a smile.

~~~

"I just wanted to thank you again Tom," she said while sitting across from me at my kitchen table and sipping some coffee I had made for her. "Thank you so much for getting my husband a maintenance job at your company. We're so lucky to have such a successful and kind young man as our neighbor. After he had lost his job and I had quit mine to take care of my 6 month old, I had no idea what we we're gonna do."

Geez, why did she have to remind me that I gave that buffoon Larry a job at my company? Even though I'm a 27 year old successful CEO for some reason I just couldn't say no to Jessica when she came to me crying two weeks ago asking if I could possibly get her unemployed, good for nothing husband, a job. He's such a meat-head that maintenance is the only department that would take him.

"Oh it's no big deal Mrs. H, we're neighbors. That's just what neighbors do, we help each other in times of need. Love thy neighbor right? It's what my mother used to always say."

"Oh just call me Jessica, Tom. And stop being so humble! You're the greatest neighbor we've ever had! If there's anything me and Larry could do to pay you back just let us know. Anything at all."

"Anything?" I said, trying not to sound too excited.

"Well anything that isn't sexual I mean." she said giggling awkwardly, perhaps remembering that I'm currently single and that she may have caught me staring a couple times.

DAMN! I was just about to ask her if I could have full uninhibited access to her ass for an hour. But of course I forgot that Jessica is super conservative and Christian. If I asked her that she'd very likely give me a slap and never speak to me again.

At this rate I don't think I'll ever have a chance to ever get a nice big handful of her posterior without going to jail. If only there were some way

"Well honestly Jessica... this might sound a bit like science fiction to you but please trust me all I'm about to tell you is completely real."

"Alright I'm listening." She said leaning in and slightly intrigued. "What could I possibly do for the man who has everything?"

"Well you see at my company, my engineers with the help of neuro-scientists are developing a machine that could theoretically allow for two consenting people to transfer minds and step into each other's shoes, literally. It could help doctors feel what their patient feels or help treat someone's prejudices by having them wear someone else's skin. The applications are endless. The only problem is it's gonna be a few years or possibly decades before it is fully functional. Currently it can only transfer a mind one way while the other remains comatose and has to be put on life support. Without a mind the empty shell won't even breathe on its own."

"You're right this does sound super scifi. Science really is amazing. But what exactly does this have to do with me and Larry? I'm not really sure what you're getting at."

Damn. How on Earth could I explain to her in a nice and innocent way that I want to get into Larry's head just so I can use his dirty hands to squeeze and knead his wife's butt?

"W-Well you see Jessica..." I stammered trying to think of what to say. Damn I just now realized I should've talked to Larry first instead so that Jessica wouldn't know I was in him. If I approach him with the idea now Jessica will know it's me and not give me access to her posterior, she'll think it's cheating. Then I'll just be stuck in Larry's oaf body working at the bottom rung of my own company. Damn I really messed this plan all up by telling Jessica first.

Come on, think Tom! You've gotten yourself out of trickier situations than this. There has to be some way to take advantage of Jessica's offer and the mind transfer machine to get full access to her amazing ass... Wait a second. I think I've thought of a crazy solution.

"Well you see Jessica. I was raised by a tough single mom who worked two jobs and struggled to afford being able to send me to college. She's my role model." I lied through my teeth, my father was the breadwinner and my mom just had the nanny look after me. "And that upbringing has just really made me admire all women. Specifically mothers. They truly struggle in so many ways. And they feel things like motherly instincts and the pain of childbirth. Feelings that no man could ever hope to truly understand."

"Wow I never knew that Tom, your mom must be a really great lady to have raised such a successful and caring young man like you." she said with a radiant smile, she completely believes my lie.

"Well she was. She's gone now. And I never got to ask her what it was truly like to be a struggling mother like that. I desperately want to know the ways she felt when she was raising me. The feelings and worries she had. The struggles. It angers me to not be able to truly understand her as an equal. What I'm trying to say is... I want to know what it's like to be a mother." I said nervously as Jessica's eyes went wide. "Jessica, you don't know how much it would mean to me if you allowed me to step into your shoes and see firsthand what it's like to be a mother. I want to know what it's like to have to cook for everyone, do all the work around the house, and be everyone's emotional support. I'd like to be able to hold a baby and not be looked at funny. To be someone's shoulder to cry on. To be the emotional center of a family. Just for 3 days."

"Tom... it sounds like you're well meaning but I can't have a young man in my house. My husband and kids would freak out seeing you doing the laundry." Jessica said with a confused look.

"Jessica I think you misunderstand me. I don't want to take over your duties while looking the way I do right now. Remember the mind transfer machine I mentioned earlier?"

"You... you're saying that... you want to enter my body? That sounds so peculiar. Why on Earth would a rich young man like you ever want to be me?"

"Jessica it's like I already said. I want to know what it's like to be a mother. I want to live your life entirely the way you do. And to do that I have to look like you."

"Well Tom, your reasons seem virtuous but if this machine is actually real, the idea of a complete stranger living with my family while wearing my face... It makes my stomach turn. My husband, my 19 year old daughter, and my baby will have no way of knowing you're not me. They'll think you're Jessica Hughes." she said softly while looking worriedly out the window towards her house.

"Yes Jessica, that's the point of the machine. To be able to truly step into someone else's shoes, into someone else's life. The experience will not just help me understand my late mother, I'll also become a better future husband. I'll know firsthand the struggles my future wife will have. Aren't there things you wish Larry would understand but he just doesn't?"

"Well I mean yeah of course there are. When we both worked the same hours he would still expect me to do the laundry and make dinner. He doesn't even wanna do the dishes sometimes. He also gets mad at me for still having some leftover baby fat, as if I could control that!" she said, quite frustrated. "He's not that bad, he just thinks I owe him all these things just because he was willing to help raise a daughter I had in high school that isn't his. It's crazy but I think I'm starting to understand you. I think you would definitely learn a lot of things from being me for a few days."

"So then, is that a yes?" I said a bit too excitedly.

"Well, it's just peculiar that's all. Tom, I don't mean to offend you but are you by any chance gay? That's just what my mind thinks when a man tells me he wants to be a woman. Do you want to get affectionate with Larry or something?"

I almost choked and spit up the sip of coffee I had been drinking. Hell no I'm not gay, the only reason I'm pulling all this crap is so I can finally get my hands on your ass lady!

"Or maybe you just want to wear my clothes Tom?" she said in a concerned tone "if you want I have some old ones I can bring over and we don't have to do all this machine business..."

"Jessica you have to believe me, no I am not gay. I'm a completely straight, hot blooded man. I don't want to wear women's clothing at all and I certainly want nothing to do with Larry. In fact, with your permission I'll probably just wear sweat pants and a t-shirt and ask Larry to sleep on the couch for 3 days."

"Well I was kinda hoping you were gay actually. If you're straight that means you might..." she started saying with a disgusted look "Well, you might just take me home and disrobe me. To look at the body of a married woman with your sinful eyes. It would be humiliating. To have a man invade me in such a way while I didn't even know."

"Jessica there is absolutely nothing sexual about this proposition." I lied as straight faced as I could. "Jessica if I wanted to do this for some disgusting and terrible reason then wouldn't it make more sense to find a stripper or something and not my own next door neighbor?"

"I guess that would be a lot easier than trying to convince me." she said as her face softened. "Besides who am I kidding, I'm an older mom and I was always made fun of in school for having such a large and unappealing bottom. If you were just trying to do something indecent and gross you'd be asking someone a lot thinner and younger I guess." She said, starting to sound a lot more willing.

"Exactly Mrs. H. Nothing sexual at all about my proposition."

"Still, 3 days? I know you got my husband a good job but-"

"One thousand dollars. I'll pay you one thousand dollars for every day." Jessica's eyes instantly lit up. I think I've finally convinced her. "That's the easiest three thousand you'll ever make. And the best part is it'll just feel like you're going into a deep sleep then boom you're awake again. Except 3000 dollars richer."

"We could definitely use the money. But gosh I still don't really know if this is even possible. Can I have some time to think about this?" she said while starting to stand up.

"Of course Jessica I personally always get a full night's sleep before big decisions like this. Just let me know as soon as you can."

She then walked away towards the front door. Her beautiful ass jiggling with every step on the way out. Torturing me and taunting me to reach out and grab it.

~~~

"Hey boss, what's the emergency you had to call me after hours for?" said John, Tom's best friend and lead engineer in charge of the mind transfer machine.

"John, I have some questions about the mind transfer machine. How is it progressing?"

"Well boss, we haven't progressed much since you last saw it. It's still only a one way transfer where the empty shell falls into a coma-like state."

"I see... and have we ever conducted any mind transfer with opposite genders?"

"Ehhh no, we've only done same gendered ones. We're not entirely sure how different male and female minds are quite yet. It could be possible. We won't know until we do further experiments. What exactly made you get so curious about my machine all of the sudden?"

"John, since you're my most trusted friend I want you to keep the rest of what I'm going to say confidential."

"Yeah you know you can trust me."

"I want this machine set up at my house ASAP and I want you to find out if a male to female transfer is possible before then as well."

"Uh sure, may I ask who is transferring into who?"

"Well remember that neighbor I told you about? Jessica Hughes?"

"Oh yeah that's the really nice and wholesome christian lady who has a huge posterior like a dump truck right?"

"Yeah well I kind of asked her for permission to transfer into her for a few days."

"HAHAHAHAHA." John laughed like a maniac on the other line. "Now what on earth do you possibly want to do that for? Tough guy CEO Tom Johnson suddenly wants to wear dresses and be a woman? The guy who was always chasing skirts in college now wants to try wearing em? This has to be a joke you're doing, are you drunk or something man?"

"John, look, I know how this sounds." I said completely humiliated and embarrassed. "But you know how much I've been obsessed with her ass. I've been obsessed for years. If I transfer into her I'll have the complete freedom to enjoy and grab her ass for 3 days straight."

"Yeah but wouldn't it make more sense to transfer into her husband? Then you could grab it as much as you want and even have sex with her if you felt like it. Wanting to transfer into her instead? It seems strange. Do you want to try on all her clothes and makeup too or something? Maybe paint her nails while you're in there."

"Yeah yeah keep joking pal. The truth is transferring into her moron of a husband was my original idea but I fucked up and told her about the machine first when I should've approached him with this offer instead. If she knew I was in Larry she wouldn't let me do anything to her. Besides from inside her I don't even have to ask for permission or be gentle."

"I guess you're right but still. You'll get to feel them as much as you want but whats the point? You won't have a hard on to jerk off with. You'll just be stuck inside her."

"Damn you're actually right for once. I'll try to think of something. I think I'll just take a lot of pictures and try to memorize the feeling of it as much as possible and jerk off after I'm back to normal. I'll figure something out."

"Yeah yeah okay I believe you man." John said in a more serious tone. "I'll have it all set up by Monday at the earliest. Just promise not to try and kiss me from inside of her alright? I'll still know it's a man in there."

"Thanks John, I can always count on you to get things done while busting my balls and keeping me in line." I was relieved to be done with this embarrassing call. I hate that someone has to know I'll be a woman for 3 days.

~~~

3 days later, around 8 p.m. Tom hears his doorbell ring

"Oh hello Jessica. Have you finally made your decision?" I said with the friendliest smile I could manage.

"Well you see about that," she said twirling her hair around her fingers nervously "Well Tom you seem like a nice fellow but I just don't think this proposition of yours is a very good idea at all..."

My heart sank into the pit of my stomach. I had been obsessing over her rear more in these last 3 days than I had ever done before. I finally thought I was gonna have my chance at it and she's about to deny me my ultimate desire.

"However," she continued "We really need the money. So I'm willing to go through with this procedure if you're willing to bump up the pay to $4500 for the 3 days. That should be enough to wipe out me and Larry's credit card debt." she said with confidence

"You know what Jessica? I think that sounds absolutely fair. I'll go grab the check right now. I trust you with it, you can deposit it the day after this is all over."

I closed the front door while I went to grab the check. As soon as it was shut I quietly jumped up into the air and pumped my fist in celebration. Finally, Jessica has given me the chance to defile her double wide booty and she doesn't even know what she's done. $4500 is nothing to me. She could've asked me for way more, even though I have no clue how much I would've offered her. She could've asked for 10k and I may have considered.

~~~

Monday day of the procedure, 12 p.m.

"She was supposed to be here at 8 a.m. sharp, Tom. I think she's a no show. I gotta go pick up my wife from work soon." said John checking his watch sitting on a chair in my basement where the mind transfer machine has been set up.

"Look, she'll be here soon John. She said she really needed that money and she even called me yesterday to go over some details about her life. Just wait another hour at least." I said with determination.

I hear the doorbell ring and almost fly up the stairs. It's Jessica wearing a loose sweater, jeans, and a pair of pink sneakers with her hair in a ponytail and no makeup on.

"Gosh sorry I was so late Tom. I was just leaving some things prepped and ready for you when you go over to my house. And also getting cold feet I suppose." she said sheepishly.

"That's alright Jessica I'm just glad you finally came." I said as I squeezed her arm reassuringly. We then started heading downstairs towards John and the machine.

"So what things did you prep anyhow?" I asked curiously.

"Oh well for instance I went out and bought some baby formula and prepared it in a few bottles so that you won't have to feed the baby... the way I normally do. I hope you weren't looking forward to that." she said coldly.

"Of course I wasn't Jessica, that's probably the one motherly experience I'd rather miss out on anyway." I said honestly.

"Well which ones did you want to experience anyhow? I've been wondering about that." She asked suspiciously.

"Oh you know just the usual. Just cooking, cleaning, burping the baby, singing some lullabies, brushing hair, gossiping with other moms, pinch some cheeks, spend all my husband's money on shoes and telling your daughter to stay away from all boys until she's 30." I said jokingly.

"Wow you might make a better mother than I thought. Do you really sing lullabies?" she asked, raising her eyebrow and joking back.

"I try but in my voice they sound menacing. In your beautiful falsetto I'm sure they'll sound lovely." I smiled as warmly as I could.

Once we made it downstairs I introduced Tom and Jessica to each other and we tried our best to explain how the machine works exactly. After that Jessica and Tom both got strapped into the machine on opposite seats by John.

"So John, how did you feel when Tom first told you about this proposition of his?" Jessica asked, smiling and trying to make small talk while the machine readied up.

"Well I think I laughed really hard at first. I thought he was just pulling my leg." said John as he plugged in a thick red cable. "But then he got really serious and made it clear he wasn't joking. That's when I started to worry that maybe he went off the deep end and would rather wear a dress than be the guy who rips them off." As he plugged in a green cable.

Jessica's face turned completely pale at the thought of John's statement that she might be letting a weirdo have full reign over her body. Who knows what he might do, she thought.

Tom immediately gives John his meanest death stare to let him know he had made a mistake.

"But then I remembered what a great relationship he and his mother had." John started bullshitting realizing he might get fired if Jessica backs out. "I think he truly does just want to know what it's like to be a mother. I don't think he'll do anything you wouldn't.

Jessica sighed with relief. John really seemed like a guy who tells it like it is. He didn't seem like the type of guy who would reassure her if he thought something bad was going to happen.