Marrying My Tomboy Wife

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He wears the dress to marry his Tomboy dream girl.
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Feinux
Feinux
107 Followers

Chris was nervous. He had been with his girlfriend Jordan since they were 18 and their relationship had survived everything that was thrown at it, including Chris being let go from his job. They were in a really good place. It didn't matter, though, he was still nervous.

When Jordan came home from work that night she walked into the house to soft jazz and a candlelit dining room. Her favourite meal was sitting on the table with a glass of wine freshly poured next to the plate. Chris was sitting at the other end, smiling. "What's all this?" Jordan asked as she walked over to give her boyfriend a kiss on the cheek.

"I wanted to surprise you." Chris replied.

"Well consider me surprised. If you keep this up, you'd made a very good housewife one day!" Jordan jested.

"Well it's funny you mention that."

"Oh? Why is that?"

Chris knelt down, "Jordan. You've been my rock through these last years and I couldn't imagine my life without you. Would you do me the greatest honour and marry me?"

His heart raced. Mere seconds had passed, but it felt like days. When she answered, he could scarcely understand what she had said.

"Yes! Of course I'll marry you!"

She picked him up off his knee and kissed him deeply. His nerves floated away like leaves on the river.

"I have one condition." She said suddenly with a mischievous grin, "I'm not going to wear the dress."

****

Two days before the wedding Chris found himself in an unfamiliar place. A beauty salon. After much coaxing by his now fiancé, he had agreed that he should be the one to wear the dress at the wedding. Jordan's reasoning was that they had already experimented with crossdressing before, and since they were both orphans, they would have no family to disappoint. Plus, their friends would get a huge kick out of it. So he had given in: he would wear the dress and she would wear the suit.

The beautician who ran the salon had allowed them to come back after hours so that no one would see Chris getting pampered. Although, that's not what he felt had happened... Over the course of several hours, from neck down, Chris had all his hair shaved and waxed. This included shaping his eyebrows and giving him fake longer eyelashes. His toenails were buffed and painted pink, and he was given fake fingernails that were also painted pink. He had grown out his hair to about shoulder length, and so it was styled in preparation for the final touches on the big day. Chris admitted to himself that it was quite enjoyable to be pampered, even if it was painful at times.

****

The big day had come. Chris finished his bath, shaving his face one last time, and applied an assortment of lotions and moisturisers at the request of the beautician. She was there when he came out of the bathroom. She motioned for him to sit down at the mirror. She began to style his hair and placed it in a classic bridal bun before she turned him away from the mirror to begin applying the make-up. She applied a light coat of foundation, followed by a natural pink blush. Then came the light eyeshadow and mascara, followed by bright red lipstick and a clear lip gloss.

When Chris turned around he couldn't believe what he was seeing. "Up to this point I did not think there was any way I could be made to look this beautiful." He told the beautician.

"You are some of my best work. You have excellent bone structure, so it was a privilege to be able to make this a reality." She replied smiling.

It finally came time to get ready. Chris had enlisted Kimberley to help him get ready. She was Jordan's best friend, and for the wedding she would be the best "man". When he walked in to the hotel bedroom he found a number of items on the bed. There was a matching bridal lingerie set: white lace panties and strapless corset with breast inserts for the cups, as well as suspenders holding and white lace stockings and a garter. He was helped into the items one by one, but unfortunately his manhood began to swell. He was enjoying the feel of all this lace on his bare skin. Kim noticed and grinned that same mischievous grin as Jordan's. She knelt down and pulled Chris' cock out of the panties and immediately put it in her mouth. Chris' initial embarrassment turned into shock, turned into satisfaction. Kim licked up Chris' member, taking him all the way into her mouth. He moved in and out, faster and faster. This was a magnificent blowjob, and by a lesbian to boot! Chris shot his load into Kim's mouth. She promptly swallowed and placed Chris' cock back into the panties, tucking it up beneath to hide the bulge. "Not a word of this leaves the room." Warned Kim.

"Not a word." Chris agreed.

Next, Chris was put into a pair of white two-inch heels. Any higher and he would tower over his "groom". He had been given some practise at home in the months leading up to the wedding and was pretty efficient at walking in them now. Finally, came the dress. It was a strapless ballgown that was picked out for him by Jordan. It was quite form fitting in the torso but the skirts billowed out from Chris' now shapely hips. Once the whole outfit was on, the veil was placed on his head and he turned to face the mirror. "What a beautiful bride!" he cried, "If it wasn't me, I'd want to marry me!"

"If I didn't know better, even I'd want to fuck you!" said Kim.

****

The whole ceremony was a blur. Jordan had turned up in a very exquisite three-piece suit, and with some make-up had made her face more masculine. She wore a cheeky grin through the whole day that Chris had noticed, but thought nothing of. They danced and drank throughout the reception and everyone enjoyed themselves. All the guests were so taken aback by how good Chris looked as a woman. There was the odd jibe about how he should consider taking up netball or cheerleading, but it was all in good fun.

After a while Jordan leaned into Chris' ear, "My beautiful bride, let's get back to our hotel room where I have a wonderful surprise for you."

Chris and Jordan made their way back to their hotel room. As the door closed Kim grabbed Chris and pushed him up against the wall, kissing him passionately. She then pushed him onto his back on the bed and kissed him again. This wasn't the first time Kim had been the dominant one, but it was the first time while their roles were reversed. Jordan sat on Chris's groin and he felt something he never had before. He pushed her up, and opened the fly on her trousers. Out of the fly flopped an 8-inch ultra-realistic dildo. Something came over him and he didn't hesitate as he put the dildo in his mouth. "Oh good," Jordan said, "I was worried I would have to talk you into this."

Chris continued his work on the dildo, incorporating all the different methods Jordan and Kim had used. Jordan moaned as he took the dildo deeper and deeper. She started to push her hips back and forward. Then she pushed him off her new cock, Chris still hungry for it.

"Roll over." Jordan demanded, "Now you're my wife, I will be wearing the pants. You will do as you're told."

Chris rolled over, and Jordan lifted the back of his dress to reveal his smooth arse in soft lace panties. She unhooked the suspenders and tore off the garter. She then slowly glided down the panties to be around Chris' ankles. She placed the head of the dildo onto Chris' anus, and he recoiled slightly. She grabbed him around the waist and slowly pushed the dildo into Chris. He let out a high-pitched moan, pleasure mixed with a minute bit of pain. Once he relaxed his arse it started to slide in easier.

"Take it all!" exclaimed Jordan as she pushed the dildo balls deep.

"Fuck me! Fuck me harder!" Chris cried out, almost unwilling and automatically.

"Do you love being my slut?" she asked as she started to pound his arse.

"I love being your slut, daddy!" he replied, "Harder!"

She continued fucking him for several minutes until both Chris and Jordan reached an unbelievable climax and they both came together.

Jordan rolled Chris over onto his back and licked up all his cum from off him and kissed him, passing his cum into his own mouth. "Now swallow, slut." And he did as he was told. They took off his wedding dress and left him in his bridal lingerie. Exhausted, they embraced on the bed with Jordan's cock pressed gently between Chris' arse cheeks and fell asleep.

When they woke the next morning they found a note pushed under the door. It read "Dear Jordan and her 'slut'. We heard you having a good time last night. See you at breakfast ;)" and it was signed by Kim and the rest of the bridal party. Jordan and Chris looked at each other and smiled. "Well, wifey, shall we get ready for breakfast?" Jordan asked.

"I thought you'd never ask."

To be continued...

Feinux
Feinux
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AnonymousAnonymousabout 1 year ago

Fun story,,

AnonymousAnonymousabout 1 year ago

This is a great way to start a story. Please continue to build their experiences and his learnings as he obviously hasn't been accepted as the masculine partner. Does the female husband want an old fashioned wife or some other variant. How well does he get accepted by other housewives family friends etc..maybe he only gets masculine for the sex act as her lovely male lover. I look forward to your next contribution.

AlexBaileyAlexBaileyabout 3 years ago

I relate! I've been the fem-boyfriend to a loving tomboy.

I wrote about it too. :)

AnonymousAnonymousover 4 years ago
please continue

Great job .your stories are too short but well done

Tootight1Tootight1over 4 years ago
loved it

Lets face it folks, some are dominant , some are submissive, that's life. I wish them well. I gave it a 5, and wish it could have been more. This is not to say the marriage may go south in the future, as background was not provided for that assumption.

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