Pegged to Heaven A Cross Dressing Husband Gets More Than He Bargained For

By Chloe Jones

I guess if you saw us day today, you'd never guess our secret. You'd certainly never guess mine. I'm just an average, pretty manly sort of guy, and my wife Michelle is a classic girl next door. Pretty, feminine, and womanly.

In fact, if you saw us during the week, you really wouldn't guess. Even if you caught us in the bedroom, you still wouldn't guess. You'd probably find Michelle on her knees with her cute little mouth wrapped around my cock, or me on top of her pounding away. We have a very good sex life, and we like to think of ourselves as adventurous.

Actually, if you didn't know us and saw us at the weekend, you probably wouldn't guess anything was unusual either. You'd still just see a woman, on her knees, pleasuring her husband, bobbing her head up and down, or bent over in front of him, letting him enjoy her body.

You would never guess how kinky we can be unless you got up really close. Then you might realize it isn't Michelle on her knees sucking the cock; it's me, in my best dress, wig, and all my makeup sucking away like a little bitch. And you might then notice that the guy that's bent me over and is about to abuse my little hole is actually Michelle.

I'll admit it, we both love to crossdress, and we have a hell of a lot of fun doing it. But this isn't just the usual sissy guy that always dresses as a woman. I only do it sometimes. I'm quite happy bending my pretty little wife over and pounding her. But every once in a while, it's nice to reverse the rolls and get Pegged To Heaven.

• Language: English
• Publisher: SABooks
• Release date: Feb 2, 2022
• ISBN: 9781005414511

Chloe Jones

Juliana Jones is a writer of fantasy and speculative fiction. She lives in a house with too many plants and likes to collect and create art of all kinds. Themes in her work include the relationship between humans and nature, loving across differences, and vengeance.

Book preview

Chapter 1

It's Friday night, but it's Date Night for my wife and me. Most couples have date nights on Saturdays, but we have it on Friday nights to get an early start on the weekends. 

Michelle and I have been married for a little over two years now, and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 18. I met Michelle when we were in college in 2005. She was studying law while I was in the IT field. We met at a college party, and there was an instant attraction between us. I would say that it was love at first sight, and we've been together ever since that night. 

We've always had great sex, and I had found Michelle's preference to take control in bed really hot. In our second year of college, I finally found the guts to reveal my secret to her. Most girls I dated had found that to be utterly disgusting and had broken up with me over it, but after many heartbreaks, I finally met my true love. 

Michelle was not like most girls. I was amazed at how understanding she was of my fetish, even supportive of it. I had never expected someone to understand it as well as she did; she even started to help me. We experimented quite a bit after I opened up to her about it. 

She helped me choose the right outfits to wear that would suit my body and emphasize the right places and had helped me become quite adept at make-up techniques. She even called me by my CD name, Jennifer, or Jenny for short. Our sex life improved quite a bit after that. She often preferred me being dressed while we had sex, and eventually, she introduced anal play in the bedroom. We started with her finger fucking me, and we gradually moved on to using small dildos and butt plugs. Although she took charge in our relationship, it wasn't until our first year of marriage that we tried pegging. 

She loved the power of the role reversal between us, and I enjoyed her control over me while she wielded her strap-on. Eventually, Michelle started embracing a more masculine role whenever I took her cock up my ass. She would dress up more like a guy while I dressed up all sexy for her, and we would usually end up fucking like rabbits. 

She suggested once that we re-enact our wedding night as part of a fantasy role play where I dressed up in her wedding dress, and she dressed up in a dapper tuxedo. 

She asked me to call her 'Mike' that night, and the sex was amazing! That is where she got her manly name from. Calling her 'Mike' in the throes of passion only made her pound me harder, and it was definitely the best fucking I had received. Of course, we did have vanilla sex every now and then, but we had both discovered that the sex was always hotter when we switched roles. 

This week had been a pretty busy one for Michelle. She'd been coming home late because of a new client that her firm had taken on and was stressing about her workload. So this morning, I had suggested that she try to get home early and maybe 'Mike' and 'Jenny' could have a date night. She seemed pretty enthusiastic about it, and we agreed that tonight we'd spend the night at home with some take-out and a movie, with a good sex session for dessert. 

I mainly work from home as a Technical Consultant for a Finnish company and mostly only leave home when I have meetings or when a client faces some significant issues. So it was easy for me to get everything ready for our evening in. I was getting really excited, and my mind began to wander with possibilities about tonight. Around 5pm, I called up Michelle at work to see if we were still on for tonight. The phone rang, and she picked up on the second ring. Hey babe, she said, sounding and stressed. 

Hey honey, what you up to? I asked. 

Just busy with this ton of paperwork lying on my desk, it's beginning to look like a pigsty in here, she said. I chuckled upon hearing that, mostly because I know Michelle to be an organized person. She doesn't like anything at home or at work to be messy at all. 

You find that funny? she asked playfully, irritated with my laughing at her. 

Yeah, kind of. Especially since I know how much of a neat freak you are, I said, this time trying to control my laughter. 

I just hate it. Just when I think that everything is going to get better, more paperwork gets shoved on my desk! She sounded really stressed, and I wondered if she would end up working late again, canceling our date tonight. 

Well, are we still on for tonight? I asked her, hoping that she could still make it. 

Yeah, yeah. I've already told the boss that I'm leaving on time today and that I really need to de-stress and relax, she replied, her words comforting me a bit. 

Ok. That's good to know! Can you pick up some take-out on your way back home? 

Yes, I can definitely do that. What are you in the mood for? she asked. 

I don't know. Just get whatever you want. I replied. 

How about I get us something from the Golden Dragon? 

The Golden Dragon was one of our favorite Chinese restaurants in the city. 

That sounds fine, babe, I replied. 

Ok then. Have you decided on a movie for tonight? she asked. 

Yea, Basic Instinct, I said with a Cheshire cat grin. 

You know, if you turn on something like that, I basically won't be able to keep my hands off you, she chuckled into the phone. 

That's the idea! I said in a sexy feminine voice. 

You're getting me really horny now, and the sexy voice isn't helping at all! 

What can I say? I love getting you worked up, I snickered. 

You know you're going to pay for that later tonight! 

Promises, promises! I sighed. 

You're such a tease! she retorted. 

Well, you better get back to work if you want to get home early, I said. 

Ok, bye. I love you, she said, and I heard the receiver click on the other end. 

I love you too, babe, I replied, beaming. 

Now, I was even more excited. Mainly because we would get to have some intimate time today, so I spent the rest of the evening getting ready. First, I took a nice long shower and made sure that I was completely shaved and hair-free around my legs, arms, and chest. I spent the next 30 minutes just deciding what I was going to wear. I wanted to be ready by when Michelle got home, and I really wanted to wow her. 

I decided on a blue-colored sundress and beige-colored 4-inch strappy heels. But first, I took care of my make-up. I made sure that I kept it minimal and classy rather than going for the slutty look. I mean, we were just going to be home and having a relaxing night, which would possibly turn into some hot loving. Although, when I did slut it up, Michelle seemed to be even more turned on and would pound me like I was a whore. 

After I was done applying foundation, mascara, and a light touch of lip gloss, I put on my blonde wig that went well with my blue eyes. I slipped into a strapless black bra and stuffed the cups with silicone breast forms. They were not too large, just about a C cup size. I put on a lacy thong to match the bra and quickly got dressed. 

I was ready by 6:30pm and headed downstairs to make myself a vodka and orange. Once my drink was ready, and as I was about to sit down to have a sip, I heard the front door open. 

Hey, babe, I greeted. 

Hey, honey, she replied with her back to me while she locked the door. She turned around, looking surprised. Wow, you're already dressed, she said, smiling and looking me up and down. 

Yeah, I wanted to get a head start and be ready by the time you got home, I said, moving closer to her and giving her a kiss. 

Well, you look really good, she complimented. 

Thanks! I aim to please. I said. 

You sure do! she said and kissed me again. 

Is that dinner? I asked, pointing to the unmarked plastic bag in her hand. 

Yeah, I got us egg rolls, rice, and your favorite Szechuan chicken. 

That sounds wonderful, I said. 

She leaned in for another kiss, and our tongues battled with each other as it became passionate. I pulled away, not wanting both of us to get all hot and bothered right away, and heard Michelle sigh as I pulled back. 

Why don't you go upstairs, take a nice hot shower and get dressed and I'll just make sure the table is set for dinner. 

She smiled and replied, Ok. 

I grabbed the food bag from Michelle's hand, and as I moved towards the kitchen, she gave me a playful smack on my behind. She gave me