(Inspired by a true story)

Groomsman

Kevin and Jessica had been dating for the last two years and had been engaged for the last six months. They were ready to get married, settle down, and have a family together. However, controversy soon arose as the wedding plans were being formulated. Upon given the list of groomsmen by Kevin, the always curious Jessica did a background check on them all. Nothing too serious, just an online program that looked through their criminal histories, rental histories, property acquisitions, and so forth. When it came to one particular, groomsman, Sam, there was nothing.

Frustrated by this, Jessica looked over her fiance's Facebook friends and found Sam among them. They were mutual friends and had met each other occasionally. Looking through Sam's photos, she found a sudden lack of them during his teenage years when Kevin and Sam went to high school together. In contrast, all of Kevin's other friends had loads of pictures of their high school antics.

Curiosity getting the better of her, Jessica looked over each and every photograph of Kevin and his friends during their high school years. She frowned slightly irked by pictures of Kevin's ex-girlfriend. She reminded herself that they had made a rule not to go too deep into each other's previous relationships. Indeed, Jessica wasn't too eager to discuss her ex-boyfriends in any kind of depth and thankfully Kevin didn't care.

Jessica eyed the teenage girl in the photographs. She had long blond hair, a feminine physique, but also appeared athletic. Her name wasn't tagged like all the others nor was it mentioned in the picture description. It was then that Jessica started seeing some odd similarities.

"It couldn't be," she said to herself.

---

At the local bar, Kevin, Sam, Ryan, Joe, and Mark played a game of pool over drinks. "I'm so happy for you, man. This is going to be so wild for you," Sam said giving Kevin a drunken hug.

"Hey, you'll get there, too," Kevin said to him.

"Not in this bar," Sam said looking around.

"You are the most judgemental of all of us," Ryan chided.

"It's because I'm a subject matter expert on women," Sam said obviously.

"I'll give him that," Joe agreed.

"So, how do you know if a girl's interested in a guy?" Mark asked.

Sam looked around eyeing all the women in the bar. "She's interested...and she's interested," he pointed them out.

"You got the gift," Kevin said as Joe and Mark walked over to them.

"More like a curse if you ask me," Sam frowned.

"We'll get you laid eventually. That is for damn certain," Ryan assured him.

"Enough about me. How's Jess?" Sam asked.

"She's great, really excited about it," Kevin smiled.

---

As soon as Kevin came home, Jessica ambushed him. "Why the fuck didn't you tell me about this girl?" she demanded showing the picture of the girl in question on her phone.

"My highschool ex-girlfriend? What does it matter?" Kevin asked defensively.

"She's with all of your guy friends you still hang around. Where is she now?" Jessica asked.

"Fuck if I know," Kevin said dismissively.

"I know who she is," Jessica said accusingly.

"So, what's the big deal," Kevin wondered not taking her seriously as he sat on the couch.

"She's Sam," Jessica revealed.

Kevin gave her a blank look. "The fuck?"

"It all makes sense. Why doesn't Sam have pictures back to his childhood years? Why does he suddenly appear in your inner circle during the time you were at college?" Jessica asked.

"Maybe I actually met him in college," Kevin suggested.

"Stop lying to me. The girl in this picture has the same facial features as Sam. They're the same person," Jessica said becoming upset.

"You're being a crazy bitch, you know that?" Kevin said to her.

"Answer the fucking question. Is this Sam?" she demanded while holding her phone.

There was a long awkward pause between them. "It is," he said finally.

"A fucking knew it. Why would you lie to me?" she asked offended.

"This is a complete invasion of privacy. How did it even occur to you to background my friends? I mean, what the fuck?" Kevin asked pissed-off.

"You're making your ex-girlfriend one of your groomsmen, that's what's fucked up," Jessica said angrily.

"I can't handle this, right now. I'm going to bed," Kevin said getting up and stumbling his way back into his room.

---

The next day, Jessica tracked down Sam at a mechanics garage where he worked. "Hey, Jess, what's up?" he asked.

"I know the truth. I just wanted to hear it from you," Jessica said scornfully.

Sam gave her a WTF look. "What truth?" he asked.

"Did you or did you not fuck my fiance in high school?" she asked point-blank.

"What kind of question is that?" Sam asked offended.

"I'll ask you again, did you or did you not," Jessica insisted.

"It's a sick question and I'm not going to answer it," Sam refused.

"You've told me everything I needed to know," Jessica said angrily and took off.

"Well...shit," Sam realized and quickly gave Kevin a call to warn him.

---

Kevin was armed and ready as Jessica stormed into the apartment. "You fucked her, didn't you?" she asked.

"Who's her?" Kevin asked.

"Sam. You fucked her," Jessica accused.

"Alright, this has gone far enough," Kevin told her off.

"Tell me the truth or this wedding is off," Jessica said to him. "Our relationship has to be based on trust and right now I'm not feeling it."

Kevin sighed. "When Sam was a girl, yeah, we fooled around. She wasn't my girlfriend. It was like a one-time thing."

"She's still a girl and you want her as your groomsman?" Jessica said unimpressed.

"Sam is a man, period. He transitioned in college, got his breasts removed, and went on testosterone," Kevin explained.

"And why didn't you tell me?" Jessica asked offended.

"Because it wasn't anyone's business," Kevin excused.

"Do the rest of the guys now? Of course, they do. The only one that doesn't know is me," Jessica raged.

"Look, there are secrets we guys have that we don't share with women. You do the same with your girlfriends. It's just how it is," Kevin said.

"But Sam isn't one of the guys. She's a woman you fucked and now you want her at our wedding front in center. I don't recall inviting any of my ex-boyfriends to the wedding. Maybe, I should," Jessica said argumentatively.

"Knock yourself out. I don't give a fuck," Kevin said finally.

"You...don't...give a fuck," Jessica repeated with a wide-eyed expression.

"Okay, I would prefer it if you didn't. It would be awkward but it's up to you," Kevin said.

"I thought we had a rule that our exes wouldn't be involved in our lives," Jessica reminded him.

"Sam isn't an ex. He's my bro. We drink, we race cars, we play video games, we paintball, and we go hiking. He's like my best friend," Kevin said defensively.

"How am I supposed to know that's what you two are really doing? Does she still have a vagina?" she asked.

"Well...yeah," Kevin said awkwardly.

"Could you get her pregnant?" Jessica pressed.

"Maybe, I don't know," Kevin theorized.

"Then, she's a woman and you've been cheating on me with her," Jessica said outraged.

"That crosses the line. When he came out as a man, it was over forever between us," Kevin said annoyed.

"How am I supposed to know that?" Jessica asked.

"You trust me," Kevin said obviously.

"My family will freak if they know what Sam is," Jessica said.

"Then, don't tell them," Kevin said.

Jessica gave him a flustered look. "I don't want her as a groomsman. If you want her up there, put her in a dress where the bridesmaids are," Jessica demanded, and then went to her room.

"Fuck me," Kevin sighed exhaustedly from the fight.

---

Sam came over and played video games with Kevin while Jessica was out. "I'm sorry, man. I don't know how she found out all of a sudden," Kevin apologized.

"It isn't the first time I've been outed. It won't be the last," Sam rolled his eyes.

"She doesn't want you to be one of my groomsmen. She sees you as my ex and not even as a man," Kevin revealed.

Sam gave Kevin an offended look and then an expression of resignation. "So, what are you going to do?" he asked softly.

"I'm going to tell her to get fucked," Kevin said resolved.

"What you got going with Jessica is a wonderful thing. She's attractive, smart, funny, ambitious, and, from what you tell me, great in bed. Don't let me spoil this," Sam said sacrificially.

"If she won't accept you as you are, then she's simply not the one," Kevin said stubbornly.

"You're never going to find the perfect girl. So, she's a little transphobic. That isn't her whole being and maybe she will grow out of it," Sam said.

"When we went out camping together...did you ever think...maybe we should do it?" Kevin asked seriously.

Sam gave him an odd look. "No, fuck no. And if we did do it, I would be the one penetrating you."

"This just so weird to think about," Kevin admitted.

Jessica came home and watched the two of them kill bad guys on the TV. She gave Sam an uncomfortable look as jealousy swelled within her. "Can I talk to you, Kevin?" she demanded.

Kevin got up to talk to her behind closed doors. "I don't want you two together at the apartment when I'm not here," Jessica said seriously.

"We're just playing video games and drinking beer," Kevin excused.

"One thing leads to another. Would you be okay if I was with a guy and you were gone?" she asked.

"Not really," Kevin admitted.

"So, there you go," Jessica said obviously.

"Sam isn't a woman, and stop calling him she or her," Kevin lectured.

"Send her away and I'll fuck you, right now," Jessica offered.

"You serious?" Kevin wondered.

Jessica nodded feeling overly competitive against Sam in the other room. "Okay," Kevin relented.

As they made love, Jessica felt the need to be more aggressive as if competing with Sam. As she was having sex with Kevin, she imagined what Sam looked like under his clothes. Did his chest still show signs of his breasts? Did his clit look different under hormone therapy? She couldn't help but think back to Sam's picture as an attractive woman. Finally, she came as she fantasized about all these possibilities forgetting that Kevin was even there.

---

A week before the wedding, Kevin and Jessica brought their friends to a pool party. Jessica wore a red bikini and was comfortable with her figure in comparison to her other friends. The guys were shirtless already playing water polo. Sam was the only guy not playing wearing a shirt as he hung out on a lounge chair wearing sunglasses. Jessica stared at him for a little too long.

"Doesn't he look cute?" Ashley, her friend, remarked.

"What makes you say that?" Jessica asked giving nothing away.

"Just look at him. He seems so much more mature than the other guys," Ashley gushed. "I'm going to go talk to him."

"Ashley, don't. He's bad news," Jessica warned.

"A bad boy?" Ashley questioned.

Jessica whispered into her ear. "Really? Wow," Ashley said amazed and completely deterred. Jessica then went over to Sam as he played on his phone. "Not getting in?"

Sam gave her a fake smile. "Wouldn't want to get my shirt wet."

"Then just take it off," she challenged.

"I don't want to show off. It could make the guys uncomfortable," Sam excused.

"And what of the girls? You do like girls, don't you?" Jessica antagonized.

Sam sighed, got up, and reluctantly took off his shirt. Jessica was expecting his chest to be heavily scarred and warped due to his surgeries. Instead, it looked completely normal and tone surpassing the other guys in the pool. Jessica stared at him in wonder looking for any imperfections. His nipples were the right size, no indication of scars, and there was even hair on his chest.

"You coming in?" Kevin asked him.

"Be right there," Sam said as he kicked off his shoes.

Jessica, again, expected to see unusually small feet like that a woman but it was not the case. Sam's feet were of average size with some hair on them. Sam then went into the pool and started playing competitively with the rest of the guys.

"You sure about him?" Ashley asked her.

Jessica gave a flustered look and turned away.

---

As the days counted down, the boys went to the local tailor to rent out their tuxes. Sam looked uncomfortably being there. "What's up with you?" Ryan asked him.

"I don't think I should be doing this, after all," Sam said.

"Why the fuck not?" Joe asked.

"Jessica knows about my past...," Sam said awkwardly.

"Damn," Mark shook his head.

"Well, so what?" Ryan said dismissively.

"She doesn't want me as a groomsman," Sam said.

"Well, that isn't her call to make," Joe said.

"Exactly, fuck her," Ryan agreed.

"What if she cancels the wedding over it?" Sam asked concernedly.

"She won't. She's bluffing. That's what all women do," Mark said.

Sam gave him an odd look. "But what if this isn't a bluff. I can't ruin this for Kevin."

"If she is what you're saying she is, then this marriage won't last, anyway. The groom invited his people, the bride invites her people, and neither of them gets a say on who the other can or cannot bring," Ryan said adamantly.

"What if your future fiancee brings an ex-boyfriend to the wedding?" Sam asked.

"I'd be pissed off, to be honest, but it's her decision. I'm telling you right now, that night it will be angry wedding sex," Ryan said.

"I don't think an entire person's worth is based on this one thing. Jessica is great for Kevin and you can't expect perfection," Sam said.

"I know you don't have your balls, yet, so listen up," Joe said to him. "When you're the man, you have to lead. If he backs down, he will be forever whipped and will never get that confidence back."

"Not if I make the decision for him," Sam said thoughtfully.

---

At the gym, Kevin and Sam worked out with the weights. "I'm going to back out as your groomsman," Sam said to him.

Kevin suddenly lost control of his weight forcing Sam to spot him. "What the fuck for?" he asked disagreeably.

"I can't be the thing that breaks you two up. I won't be the cause," he said.

"That's really fucking noble. And what am I supposed to do? Accept your resignation? The fuck I will," Kevin said.

"I'll simply not go even if you ask me to," Sam said simply. "If it's a choice between me and Jessica, the choice is clear."

"The choice is clear. This isn't about whether I love her more than you. This is about principle. Beyond the bigotry of this being completely transphobic, loyalty and respect are really damn important to me. If she cancels the wedding, it's on her," Kevin said.

"But if I'm not there...," Sam let it hang.

"If you're not there, the wedding is canceled. Does that make it easier for you?" Kevin asked him.

The two walked into the locker room and grabbed a towel. The gym locker room actually had shower stalls for more privacy, it was the reason why they picked this gym. Kevin undressed first feeling completely comfortable doing so in front of Sam.

"Alright, I got you covered," Kevin said as he made sure no one was looking.

Sam quickly undressed and got into a shower stall so no one would notice he was the only man in the room without a dick. When they came out, Kevin, again, gave Sam cover to put his clothes back on. The two then walked out of the gym like it was nothing.

---

Mere days before the wedding, Jessica put her foot down. "I don't want her as a groomsman or at the wedding at all," she demanded.

"Well, that's too bad," Kevin said standing his ground.

"I'll cancel the wedding," she threatened.

"We already have everything set up. It would be a huge waste of money and we would be done, finished, over," Kevin said dramatically.

"It's me or her," Jessica said.

"You keeping saying 'her'. Haven't you seen enough of him to know that Sam isn't a woman? I mean, where's the long hair, where's the feminine face, where are the baby-making hips, the slim legs, the tits?" Kevin listed off.

"If you don't have a cock, you're not a man," Jessica said simply.

"You're being completely irrational," Kevin pointed out.

"Am I? I have a right to feel uncomfortable about this. She is your ex, you had sex with her, and she's with you all the God damn time. You spend more time with her than me," Jessica raged.

"So, you feel uncomfortable? Deal with it," Kevin said dismissively.

"I'll tell your parents," she threatened.

"Fuck," Kevin sighed knowing they wouldn't be thrilled and would probably arm-twist him to disinvite Sam. "Is this what you really want? A bitch of a husband that folds when it gets tough? Don't you want me to stand up for myself?" he asked her.

"I want you to stand up for me," Jessica told him.

"What can I do to convince you that Sam is a man?" Kevin asked her.

Jessica gave him a blank look. "You're not going to like it."

"Try me," Kevin rolled his eyes.

---

Kevin and Sam had a walk in the park to discuss Jessica's ultimatum. "I need you to give me a solid," Kevin began.

"Sure, anything," Sam replied.

"I need you to fuck my fiancee, tonight," Kevin said finally.

There was a long awkward pause. "The fuck?" Sam wondered.

"She won't be convinced you're a real man until you fuck her," Kevin said.

"There's so much wrong with that. I can't fuck your fiancee. That's cheating," Sam said.

"Not if I give you permission," Kevin said.

"I got standards, too. I mean, I want to have sex with someone I actually want to be with," Sam said.

"Yeah, right. I know you've slept with girls using Tinder. Look, I know you can do this. If she still says no after all this, then Jessica and I are finished," Kevin said.

"And if this goes according to plan, what then? You will always remember that I fucked your wife," Sam said.

"Like how I will always remember how I fucked you? I don't even remember most of it," Kevin said.

"It was the biggest mistake we ever did. It made it weird between us," Sam recalled.

"But we got over it, didn't we?" Kevin asked rhetorically.

"Have we? Do you ever wonder what it would have been if I hadn't transitioned? Do you fantasize about me still being a girl?" he asked.

"Bro, I fantasize about everything. You know how diverse my porn collection is," Kevin reminded him.

"Okay, I'll do it," Sam relented. "But I want you to know, I shouldn't have to do this."

"I know. Make sure you fuck the shit out of her," Kevin said giving Sam a bro-hug.

---

Sam awkwardly came by the apartment that evening with little enthusiasm. He took a deep breath and came inside, Kevin wasn't at home by design. "I'm not really interested in talking about this. You know why you're here," Jessica said rudely.

"Yep," Sam sighed.

"So, show me what you can do. You're in charge," Jessica invited.

Sam could already tell that Jessica was a little tipsy and had no enthusiasm for this, either. "You want a real man. Alright, we stop when I'm done with you," Sam said to her.

"Fine, just don't bore me," Jessica allowed.

Sam expertly took her dress off her shoulders and then unclasped her bra. "You should be an expert on this. How many years did you wear a bra?" Jessica antagonized.

"God damn," Sam muttered as he was done. "I'm in charge which means you shut your mouth," he told her off.

Jessica rolled her eyes as she was stripped down to her panties. Sam, meanwhile, took off his shirt, his shorts, and then his boxers. Jessica turned around and saw Sam's backside. From all appearances, he looked like a man with lean muscle and very little body fat. She couldn't help but feel turned on by him.

"Let's go to your room," Sam ordered her still having his back to her.

Jessica complied and then got on the bed. Sam turned off the lights as he came in. "So, what are you going to do? Play with my breasts, lick me silly, and put fingers inside me? Maybe even scissor me?" she asked condescendingly.

"Jess, shut your mouth," he ordered her.

He walked over to her and got on top of her. He immediately began kissing her and placing his thumb on her right nipple rubbing it just right. Sam gave her tongue as he dominated her mouth. Jessica played along pretending he was a real man. With his other hand, he went inside her panties and started rubbing her clit. Jessica sighed as she realized he was warming her up. Unlike Kevin, she didn't feel his hardness.

Sam took his time knowing everything was on the line. He kissed Jess down her neck and then made his way to her nipple expertly sucking on it. "Did Kevin do the same to you?" she asked him.

"Not another word," he warned her.

Sam hesitated as he recalled that fateful camping trip when Kevin and he drunkenly had sex in their tent. Putting the memory aside, Sam went back to work to stimulate Jessica's body. Finally, he lowered himself down on her and began to lick her generously. Jessica tensed up as she was being licked in her most sensitive spot. Kevin had always been squeamish about going down on her and even when he did, he never did it right. Sam expertly got Jessica to moan, squirm, and quickly have her first orgasm of the night.

Jessica cried out as she felt the best oral sex she had ever been given. Still, it wasn't enough. Lesbians could do the same thing. So what? Sam then placed a finger inside her and moved around feeling it well lubricated. He then placed another finger inside. Jessica rocked her hips to his movements. At this point, nothing he was doing was surprising to her. He was going to need to do better than that to satisfy her.

Once he was sure he was ready, he went down to his crotch and squeezed his fake testicles. Immediately, his fake penis was at attention. Without Jessica realizing, he had been wearing the strapon around his waist inside his boxers the entire time. It had been his dream to eventually have the device attached to his body permanently but this would have to do for the time being. He placed the peach-colored fake penis at her entrance. It looked and touched realistic featuring veins and a circumcised head.

Jessica felt Sam's cock enter her with some surprise and then realized what was happening. A part of her wanted to back out and just give up on her protest. But the more stubborn part noted that even Lesbians used strapons. That didn't make them men. Sam went all the way to the hilt testing to see how tight and wet she was. Satisfied he wouldn't hurt her, he began to thrust harder. With his muscular arms, he looked down on Jessica as he fucked her missionary style.

Once he was more comfortable with her, Sam picked up Jessica off the bed and kept a tight grip on her hips as he stood up. In the standing suspended position, Sam thrust into her as Jessica wrapped her arms around his neck for dear life. Sam kept it up carrying her 120 lb weight with his arms while keeping perfect balance with his legs. Jessica was speechless as she acknowledged his strength.

Sam then walked her over to a desk and placed her on it as he kept hold of her hips thrusting her good and hard. Jessica shuddered as she felt another orgasm go through her. At this point, she was starting to lose resolve. Sam then lifted her off the desk and then in a quick movement turned Jessica around so they were both facing forward. Sam slowly lowered her upper body to the floor in a controlled motion. Jessica put her hands on the floor to steady herself as her legs were wrapped around his hips. While having his hands wrapped around her hips, Sam thrust inside her in the advanced cow position. Jessica felt overwhelmed as Sam keeping her hips and legs in the air. If she moved, she could end up falling giving him perfect control over her.

Sam then slowly got to a knee taking Jessica's legs down with her. Immediately, he penetrated her deeply in the doggy-style position. Jessica could barely stay on all fours as Sam fucked her. He was just so fast and so hard. Eventually, she dropped to the carpet with Sam following her down. With him on top of her, he continued to thrust until Jessica cried out.

"No more, it's too sensitive," she said to him.

Sam relented withdrawing from her. Sam helped her back to her feet and then to the bed seeing how shaky her legs were. "I'm sorry for not calling you a man. I've never been fucked so hard and strong as you have. Kevin never came close to this," Jessica said to him.

"Well...thanks," Sam said awkwardly.

"I'm sorry it came to this. I really am. Is there anything I can do to make it up to you?" she asked.

"Well...you do have a cute friend," Sam smiled referring to Ashley.

---

At the wedding ceremony, Sam was dressed up in a tux and was all smiles for the pictures. None of the guests knew the truth and that's the way Sam wanted it. Kevin never asked about the intimate details of Jessica's encounter with Sam. Suffice to say, the controversy was over and that was that. Kevin and Jessica made their vows, kissed, and were officially married before all.

"Hey, we missed you at the bachelor's party," Ryan said to Sam after the ceremony.

"Yeah, I was caught up," Sam said vaguely referring to his night with Jessica.

"Well, tonight we are going to get fucked up. You ready?" Ryan asked him.

"Absolutely," Sam smiled as he went to the bar along with the rest of the guys.

Kevin made the rounds getting to know all of the guests. He came upon one of the bridesmaids he hadn't met before. "I'm sorry, I haven't met you before," Kevin said to her.

"Oh, I'm Danielle. I'm really glad to be here. You are a really understanding guy," she said adoringly.

"How so?" Kevin asked curiously.

"Well...I used to be Jessica's...ex, you know, before I transitioned," she said softly so no one else overheard.

Kevin eyed Danielle in amazement that she had once been a man. Nothing gave her away. Kevin simply stared at her as he considered all the bullshit he had to deal with over Sam. "Yes, of course. No problem," Kevin said to her.

"Well, I better get back to the girls. Nice meeting you, finally," she said awkwardly.

Kevin finished his drink and shook his head dismayed. Jessica gave Danielle a hug as she came over and then noticed Kevin's sour look. She gave him an awkward look and then smiled sheepishly. Kevin rolled his eyes and went off to get another drink.

---

Author's Notes: So, ideally trans people shouldn't have to prove anything to anyone but stories are about conflicts and people learning from their mistakes and misconceptions. Many might argue that Kevin and Jessica shouldn't be together especially with the twist ending and that's completely fair.