Boyfriend Sexfight

Story Info
Boyfriends sexfight for their crossdressing gurlfriends.
2.2k words
4.29
18.6k
17
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Frank, 52 6'2", 285lbs, 8" cock (Current boyfriend)

Dom, 32 6'0", 240lbs, 9" cock (Former boyfriend)

After a round of passionate sex with Frank, he asked me if I had every had any other boyfriends. I told him I didn't, but that I had a boyfriend named Dom a few months back that had found another gurl and dumped me -- even though I had offered to share. Frank couldn't believe that he had dumped me and said he'd love to get his hands on any guy that would dump me. I didn't think much of it right away (except how protective he was of me), but a week or so later I found myself thinking about what he said and started wondering if he was serious and how exciting it would be to watch him Dom battle it out. Maybe he would put Dom in his place or maybe Dom would send us both home losers.

One night I was on my knees stroking Frank's big cock as he towered above me and I looked him in the eyes naughtily and asked him if he was serious about wanting to get his hands on Dom. He looked down at me working his cock and said he would relish the opportunity and to tell me a little about him. I told him Dom was a bit smaller and softer than him, but younger than us both and had a huge cock. It was an inch or so longer than Frank's, but not as thick. He was one of my roommates and had bullied me a bit into being his bitch after catching me dressing late one night when I though nobody was home. Frank suggested I see if I could arrange a match with him and Dom and I was so excited I hungrily sucked his cock until he groaned and covered my face with his warm, thick cum.

A couple days later I reached out to Dom and told him I had a new boyfriend that appreciated me and wanted a piece of the loser who dumped me. He laughed and told me how pathetic me and my new boyfriend must be. I told him Frank was older, but bigger and stronger than him and he just laughed again and said he'd happily put a beat down on Frank in front of me as his new gurlfriend Mandy watched -- sending us both home humiliated. I told him that if he was that confident, we should make it a sexfight with the losers having their way with the winners. He cockily replied that I must be missing his cock and he'd gladly fuck Frank and then me leaving us both used and dripping with his cum. I had hoped that Frank was OK with this and told him about it as my panty covered ass was straddling his cock later that night. His passionate fucking told me everything I needed to know, so I set up the match for the following Saturday afternoon at Dom's place.

We arrived at Dom's around 4PM. Mandy greeted us at the door and I found it hard to blame Dom for the upgrade. She was wearing heels and short shorts with a halter top and loaded with thick, juicy curves. Her fake tits strained the limits of her top and her sexy ass peeked out of her shorts as she led us into the living room. I watched her ass lustily as I followed in my own heels, bikini bottom and tight t-shirt. My fake tits were much smaller, but I really worked it as I followed her hoping Frank was taking more notice of my ass than hers. Dom walked in wearing the agreed wardrobe which was a small Speedo. His soft, pale physique spilled out a bit, but I couldn't help but notice the large bulge in the front -- even though he wasn't even hard. We reviewed the ground rules as Frank took off his clothes. I loved his big, strong body as he worked his way down to his own Speedo. I wanted him to take me right there, but held my feelings in check as best I could though my biking bottom quickly started filling with my growing gurl cock.

The rules were simple -- wrestling only until someone submits or makes their opponent cum and is declared the winner. Frank and Dom -- though both liking gurls -- had never considered themselves gay, but in this situation, both were eager to prove their dominance, so didn't really think of it as a gay act. From my own experience, Frank was always much more loving and attentive to my pleasure than Dom who used me as his fucktoy only - making suck his cock and fucking my ass with no interest in my pleasure. I was hoping this would give Frank an advantage as Mandy and I sat across the room from each other enjoying watching our boys ready to add another conquest to their resume. By this time, I was so horny I just needed a cock in my mouth and ass, but wanted Frank to take Dom down a notch.

They both circled each other a bit before Frank moved in to try and secure Dom with a bear hug. While not very athletic, Dom saw him lunge and moved quickly to slide out of the way and slipped behind Frank. He reached up under Frank's arms and secured him in a full nelson.

"Nice move baby!" Mandy shouted happily as Frank was temporarily helpless with his arms extended above his head. Dom spun him towards Mandy and pulled back hard making Frank arch his back and extending his hips toward Mandy.

"Doesn't look like he fills out his speedo the way I do, does he?" Dom asked Mandy.

"No way baby!" she replied pulling down the front of Franks Speedo and exposing his big cock which was now semi-hard.

"No fair!" I protested before Dom spun him around to face me.

"Let him do something about it then." Dom said arrogantly.

I could see Frank's arms starting to strain and was wondering if this might not end up the way I thought it would. To make matters worse, I'm sure he could feel Dom's big cock pressing up against his ass.

Feeling Frank's resistance fading, Dom hooked his foot around Frank and with a push sent him sprawling face down to the floor. Before Frank could begin to react, Dom was on him like a lion on his prey. He pulled Frank's Speedo down and completely off. Frank's arms were still numb from the full nelson, so Dom to the opportunity to pull Frank's arms behind his back and tie them securely with his Speedo.

I was shocked how quickly Dom had effectively subdued Frank and was wondering if this was how Frank was going to be able to get out of this embarrassing predicament. I could tell Dom was enjoying this and was going to take every opportunity to humiliate us both.

"How's your new boyfriend looking now bitch?" he asked me sarcastically knowing that I wouldn't have a response.

"It looks like somebody needs to be put in their place," he said as he held Frank's hands with one hand and began spanking him slowly with the other.

I could see Frank trying to free himself and squirm as each smack slowly and methodically begin to redden his ass. I longed to stop Dom and soothe Frank's ass, but I had to sit helplessly and watch the punishment continue.

"It's going to sting even more when I'm fucking you shortly bitch" he laughed at Frank. Then using his weight and knees as leverage, he spread Franks legs and knelt between them. With his legs spread, Frank's ass pussy was exposed and vulnerable.

"This ass looks nearly ready for a good fuck, doesn't it Mandy?" he asked.

"That's a cock hungry ass baby -- show him what a real man can do" Mandy purred.

Dom pulled Frank's cheeks apart and slowly ran a finger over and around his ass pussy. Leaning forward, he slowly let some saliva stream down until it landed squarely in Frank's ass. Using it as lube, he slowly began working his finger into Frank's ass.

"You're going to learn to take a cock in your ass like all my other gurls bitch -- and you'll beg me for it" Dom said arrogantly.

I could feel Frank's embarrassment but was surprised to see him arch his ass up to try and help take Dom's finger.

"Wow -- we've got another slut here Mandy" Dom said, "just look at him work his ass to take more."

I was shocked that Frank was acting so submissive, but I could also see him trying to free his hands so realized that he was just buying time to distract Dom from noticing. Dom took this added attention as an opportunity to slip in another finger and I watched as my ex-boyfriend was now lustily finger fucking my new boyfriend.

Dom was about to slip in a third finger, when the Speedo he had tied Frank in came loose and Frank quickly flipped himself over - grabbing an off-guard Dom between his strong thighs in the process.

"Dom!" Mandy cried as Frank now squeezed Dom between his thighs around Dom's waist as he now laid face down in the carpet.

"That's it baby" I cheered as Frank applied pressure to Dom's midsection. I could hear the air squeeze out of Dom as he gasped in discomfort.

Dom was no match physically for Frank and in no time, Dom was nearly limp between his legs. Frank released Dom and stood up as Dom lay on the floor weakly gasping for air. He reached down and pulled Dom's Speedo off leaving his soft ass exposed. He then straddled Dom's ass and pulled his head up by his hair.

"This can end one of three ways" Frank said. "You can either voluntarily submit, I can make you submit, or I will make you cum. In all cases, you are going to have my cock in your ass, it's just a matter of how embarrassing you want this to end."

"Fuck you!" Dom whispered back showing some traces of resistance.

"Don't say I didn't give you a fair chance -- I guess we'll do this the most embarrassing way" Frank responded. "You're going to cum just like all your bitches do."

Grabbing one of the Speedos, Franks securely tied Dom's hands behind his back -- and Frank made sure there was going to be no escaping this time. Reaching for a bottle of lube on the couch, he spread Dom's pale cheeks and covered his ass pussy generously. Dom tried but could only offer minor resistance to Frank from his dominant position. Frank stroked his big cock until it was fully erect then slide in between Dom's cheeks until the tip entered his ass.

Dom groaned as his ass was stretched. I looked across the room to see Mandy looking nervous and uncomfortable. Franks inched in slowly going a little deeper each time. Dom continued to groan so Frank took the other Speedo and stuffed it in his mouth to muffle the moans. He continued to work his cock into Dom's ass until he worked in every inch.

My gurl cock was raging watching Frank slowly fuck Dom. I had never imagined anything could be so exciting. I didn't know what Frank had planned as Dom could no longer submit -- and the only option was to cum, but he always seems to know just what to do.

After bottoming out in Dom's ass, he pulled his cock out and rolled Dom over onto his back. His hands were now fully pinned behind his back as Frank lifted his legs and re-mounted him in the missionary position with Dom's legs up on his shoulders. As Frank worked his cock into Dom's ass as he had done so many times with me, I couldn't help but be jealous as I wanted his cock in my ass. I also couldn't help but notice that Dom's big cock was hard as a rock. I began to realize Frank's plan as Dom's muffled moans began to fill the room -- he was going to make Dom cum by fucking him -- just like he does to me!

I nearly came with just the realization, but could only manage to watch lustily as Dom's moans became quicker and louder. Frank was really fucking him hard and deep now and he grabbed Dom's head and forced him to look at his cock as Dom let out a final orgasmic groan and covered his chest and face with stream after stream of warm cum. His body was spasming and convulsing as he helplessly came long and hard.

I was so proud of my boyfriend and ran over to give him a warm passionate kiss of victory with his cock still buried deep in Dom's ass. I knew he was aching for release and wanted to stroke his cock, but with the victory in hand, he forced Dom to ride him straddle him and ride him to orgasm as Mandy was forced to do the same for me.

Late Saturday night, after a few hours of fucking and sucking, we left Dom and Mandy well used and covered in our cum. I had exacted my revenge and even fucked Dom as part of our victory. I was so proud of Frank and thought that he would have been exhausted when we got back to our place, but he was still plenty man enough to fuck me until we fell into a deep sleep covered in our juices.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousabout 1 hour ago

I really like your stories. Will you write something again for us?

AnonymousAnonymousalmost 6 years ago

another round of this story

Share this Story

Similar Stories

My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Micheal Finds Jamie Straight guy finds his buddy all dolled up and gets some.in Transgender & Crossdressers
Halloween Party A Halloween to remember.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories