The sun beat down against the office building in Panama's banking district. It was a hot summer day but inside the office on the twenty-fifth floor, it was cool and quiet.

Tabatha stared at her computer screen and reread the message again and then again. She then went back to her accounting and finished it off which took about thirty minutes. Once done she went to the bathroom and then made a cup of tea. When she walked past Matt’s office he wasn’t there and then she remembered he had to go to the bank. Back in her office, she read the last message he had sent her yet again.

I would like it if you fucked me with a strap-on.

What had begun as a normal chat had in some way ended up with this. She looked back at what they had written and she knew it wasn’t something she should have chatted about with her boss. At the same time, they had known each other for many years and had been through ups and downs along the way at different companies. They had the confidence to tell each other their secrets and fantasies and this was Matt’s, to be fucked by a woman up the ass with a strap-on. She smiled. The thought didn’t disgust her, rather it excited her. She had always had a bit of a dominant streak in her and this might be a way to try it out. Some field testing as they might call it. She quickly wrote an answer and then went back to work.

Matt came back two hours later and saw Tabatha deep into her accounting. She didn’t look up when he passed her office even though she couldn’t avoid his presence through the large glass windows. Maybe she was pissed, had he gone too far? They hadn’t been flirting with each other in the morning. There was no love drama or a crush from either. He was a married man with two children, she had her girlfriend and that was that. All they had done was share some sexual fantasies but maybe he had gone too far this time. He had been honest with her. She was the only person he could think of that he could tell what he wanted and he would let her do it to him.

He took off his jacket and hung it on the wall and then with anticipation and fear he typed in his password and the computer screen lit up. He opened the chat program and read the answer.

Yes, I do. When and where?

Matt let go of a long sigh of relief and looked up at the ceiling. His heart was beating. Not because he now had a way to try something out, he had fantasized about it for a long time, and he hadn’t lost an amazing friend by being a dick head. He looked over the screen at Tabatha who met his gaze and winked at him. He smiled back and then typed.

Let’s do lunch tomorrow if you know what I mean?

OK, I’ll bring a toy.

 When lunchtime came around the following day Tabatha and Matt left the office and left the secretary, Karla to handle any phone calls. It wasn’t unusual for the two to have lunch together. So, Karla didn’t think twice about it. She went back to filing her nails and waiting for a call to come in.

“I’m nervous,” said Matt as they left the parking lot and entered the traffic flow. During lunch, the traffic was almost at a standstill. “Are you sure you are ok with this?”

“I’m fine. To be honest I’m nervous too, you know.”

When they arrived at the hotel he said, “This is it, if you want to change your mind this is the time to do it.”

Tabatha shook her head. “Let’s do it.”

Tabatha and Matt had known each other for about ten years. They had started at the same company when she was just twenty years old and he was twenty-seven. He was her department manager. When he later switched to another company, he asked her to come with him and she did. This was the third company they had been at since they had met.

“I’ll take a shower,” said Matt.

When he came out again, he had a towel wrapped around his hips. Tabatha was in her panties and bra with her back turned to him. She turned around facing him.

“What do you think?”

Matt swallowed. “Fuck, you look hot.” She wore a strap-on about eight inches long and not too thick.

“Get on the bed and lie down on your stomach.”

He did and felt very vulnerable. He wasn’t sure what to expect. Would she ram the strap-on into him with no warning or what was she going to do?”

“Spread your legs,” she said.

He felt her hands on his ass cheeks and then something cold against his anus. Then the cold became warm and soft. It tickled but felt awesome. He realized she was licking his ass. He had never experienced such pleasure before and his dick grew hard under him. She kept licking and he moaned quietly into the pillow.

“We could try spooning,” she said.

Matt lay on his side and she was behind him. He felt the pressure of the toy against his anus and how wet and slippery it was from the lubrication. She pushed harder and he opened up a little and gasped.

“Does it hurt?” she asked.

“No.”

Tabatha wanted so much to drive the toy into him but held back. She was extremely horny at the moment which she hadn’t thought she would be. She had thought, I’ll fuck him since he wants to and that’s it. It had never occurred to her until that moment how much she had wanted to fuck a man and dominate him.  Being in charge, having the cock in her hand was something she had secretly fantasies about over many years. She had never told anybody and had never had the opportunity to live out her fantasy until now. But she had to be careful and go slow. She added more pressure and felt him give away.

“Ahh, ahh, fuck, that is big.”

She looked down at the toy, it was about two inches inside. She reached for the lube and added some to the shaft. Pressing a bit harder it slid in further.

“Oh fuck, I’m so horny, Tabatha. Just push it in all the way.”

“You sure?”

“Yeah, yeah.”

She did and when the toy entered with its entire length Matt gasped and swore under his breath. His legs began to shake a little and he breathed heavily.

She began to move, slowly and gently. “How does it feel?”

“Good, amazing in fact. How much is inside?”

“All of it, you have eight inches of cock in your ass Matt.”

“Oh fuck? I thought it was just a few inches.”

She kept on fucking him and the longer she did the more he opened up until it was easy as fucking her girlfriend's pussy.

Matt had never in his life experienced such pleasure and he wanted more, a lot more. “Let’s change the position to missionary.”

When Tabatha looked into his eyes, she felt good. He was at her mercy now. She was in total control and she loved it, she was getting high on it. His dick lay limp to the side with some precum oozing out. As she entered him again, he made girly noises and she laughed. She helped him put his legs over her shoulders and then she began to fuck him deeply. She loved the look on his face, the sweat on his forehead, and how his legs soon began to tremble. Her rubber cock slid in and out and his cock kept spewing out pre-cum.

Matt watched his friend as she fucked him slowly and deeply. He wanted to touch her boobs and maybe her pussy but that wasn’t why they were there. This was about her dominating him and he was loving it. Her deep thrusts gave him so much pleasure but it wasn’t only the physical. It was the fact that he was giving away his body to her to do what she wanted. He would love if she would stroke his cock, but she didn’t. She fucked him, she wanted to fuck him and that was it.

“I want to fuck you from behind,” said Tabatha.

“Ok.”

She pulled out and for a second or two Matt felt how open he was from the dildo that had been fucking him for several minutes. He rolled over on his stomach and pushed up. He placed the pillow under his chin and waited.

Tabatha looked down at the man in front of her. It felt strange that after so many years of friendship, they had ended up here. She caressed his ass cheeks and teased his balls between his legs before adding more lube to the dildo. She lined it up and then began to push. She kept a steady pressure and it entered much easier than before. When the head pushed through Matt whined and gasped.

“Are you ok?”

“Yeah, I just feel tighter in this position. It’s much more intense.”

She stopped for a while, letting him get used to her again, and then pushed on.

Matt closed his eyes and held his breath. He knew that the key was to breathe but the pain was much deeper in this position than the other. It felt like his hipbones were moving apart. Maybe this was the way women felt during birth. Tabatha began to push again and he gasped and moaned.

His anus was tight around the dildo and Tabatha could hardly take her eyes off it. The sight made her even hornier than before and it might have been that in her fantasies she had always fucked the man in a doggy position. The ultimate position to dominate. She added some more pressure and this time Mat’s anus simply opened up and she slid in all the way.

“Of fuck, that was so cool,” she said.

“What?”

“Your ass, it just gave up being a bitch and opened up.”

Matt tried to laugh but the sensation was too intense. Tabatha had been right; his anus had relaxed a little and the pain was slowly ebbing away turning into pleasure. He felt completely dominated by her. She controlled his pleasure and pain now and he loved it. The only thing that upset him was his limp dick. He had no idea why it was like that instead of being hard. He felt like it feminized him, but then again, that was a hot thought. He liked being Tabatha’s little fuck bitch. It was up to her if she would make him come or not.

Tabatha began to fuck him faster and deeper making him moan deeply into the pillow. She was wet and horny like never before. She wasn’t sure how long they should be fucking and what the result would be. She wouldn’t be able to squirt nor come with the dildo and she wasn’t sure how Matt’s dick and balls were doing as far as orgasming.

“Matt, turn over, I want to see your face when I make you come.”

She pulled out and he lay on his back with his legs over her thighs when she was kneeling in front of him. The dildo slid in easily now that he was dilated and she went back to fucking him deep and quite fast. His eyes almost rolled back and his knuckles turned white from clenching the sheets so hard. His cock was oozing cum with the foreskin pulled back. She took it in her hand and began to jerk him off fast while still fucking him.

“Oh fuck, yes, yes, oh please, please let me come,” he moaned.

When he did, he shot a couple of globs of cum that landed on his chest and then the dick kept on spewing cum like hot lava that ran over her fingers and onto his balls. When he was empty, she let go of his dick and pulled out. She knelt there watching him as he slowly opened his eyes and looked at her.

“That was the hardest orgasm I have ever had, fuck it was amazing. Thank you so much, Tabatha.”

She smiled at him. “I loved fucking you; you turn into such a horny bitch asking for more cock.”

They laughed and then he got up and went to the bathroom.

When he came out, Tabatha was dressed and looked proper in her clothes sitting on the bed waiting for him. He quickly got dressed and, on the way, back to the office they hardly said a word. Each one in their thoughts.

That night after his wife and kids had gone to bed Matt sat outside in his garden with a bottle of wine soul searching. What he had experienced previously that day had been something that now scared him. When he had fantasized about a woman fucking him, he had never in his wildest dreams thought he would experience such pleasure or come so hard. Another thing that had surprised him was how much Tabatha had put in. He had thought she would just stick it in, wait for him to masturbate, and then be over with it. She had enjoyed the entire session; he was sure of it. The way she had penetrated him, kept eye contact while fucking him and then the gleam in her eyes when he came told him she had enjoyed it as much as he had. He finished his wine and went to bed.

The following morning, they arrived at different times. Tabatha’s taxi was late so Matt was already in the office when she arrived. Walking by his office he avoided eye contact and stared at his computer screen. She didn’t pay much attention to it, because sometimes he was very busy.

By lunch time he hadn’t written her a single sentence in the chat. An hour before they were to leave, she typed, are we ok?

It took a few minutes before he answered. I hope so, how do you feel about yesterday?

Do you want the truth?

Matt closed his eyes, and wrote back, Yes.

I loved it, it was amazing, hot, sexy, dirty, kinky and I can’t wait to do it again.

Matt sighed in relief. I feel the same. You fucked me so well, I have never felt anything like it before and I want more, a lot more.

Great, I love having you as my fuck bitch. Do you know you sound like a girl when I fuck you hard?

Matt looked over the computer screen at Tabatha who stuck out her tongue at him. He typed; you make me want to be your bitch!

That night Matt couldn’t sleep. He tossed and turned until his wife woke up and told him to go for a walk or something. He put on his sneakers and went for a walk in the neighborhood. It was quiet, not even a dog barking and Matt was alone with his thoughts. And there were many. Was he gay, was he bisexual, what the fuck was he? The experience with Tabatha had been such a rush that he had no idea if he could ever be with his wife again without missing it. Then again, she had a wonderful shaved pussy that he loved to eat and it was tight around his cock. Maybe these were two completely different rushes? One was that of being dominated by a woman and having her fuck him, no, a better description was, pounding his ass. The other was that of being with a woman, fucking her pussy.

It had all started, or at least that’s what Matt thought, with him running across a video clip of a transgirl fucking a dude. He hadn’t been searching for it, just scrolling but the clip had caught his attention. Maybe it was because he had seen several trans prostitutes in the casino where he went with his friends. When he watched it, his cock became incredibly hard and it scared him. At the same time, he couldn’t take his eyes off the dude sucking that big cock attached to the beautiful woman with obviously fake boobs. When the clip was done, he looked for another and another. That night, he jerked off five times before going to bed. When he woke up the following morning, he couldn’t stop thinking about what he had seen.

The next day when he walked into the office Tabatha gave him a wicked smile and pointed at his computer. He quickly opened it and read the message.

I have a surprise for our lunch date.

Matt felt himself go hard and when he looked over at Tabatha, she winked at him. He got up and said to the receptionist. “Tabatha and I are going to the bank, and we will be having lunch right afterward.”

“Ok.”

Tabatha almost laughed as she walked by Matt on their way to the elevator. They didn’t speak on the way down since there were several other people in it but once in his car she said, “I take it you are horny?”

“Oh fuck, I’m dying here, Tabatha. I need you.”

She laughed. “No, you need a nice hard dildo up your ass.”

They went to the same place as the previous day and the procedure was pretty much the same. After he had taken a shower Matt lay on his stomach and Tabatha licked his anus until he was relaxed, she lubed up the toy and gently began to push it inside him.

Matt wanted it faster; it was taking too long time so he got up on all fours and then pushed back hard. “Ah, fuck!”

Tabatha stared at the dildo which had completely penetrated Matt. “Wow, that must have hurt.”

“Oh fuck, god, it does, but I can take it,” he said breathing fast and shallow.

She began to fuck him, and he moaned and grunted as she began to do it faster. She loved it this way, he was completely under her power. She slapped his ass cheeks and he moaned as they turned pink. She played with his balls, running her nails around them and squeezing them gently.

He then rolled over onto his back and she penetrated him with ease. Putting his legs over her shoulder and leaning forward she fucked him hard looking into his eyes. They were wide open and unfocused. She felt for his cock between them and it was limp and wet from pre-cum. She began to stroke it and leaned back a little to get a better hold of it.

Matt lifted his head and looked down at his body. “Oh, I love your cock in me, fuck me, fuck me!”

And she did while stroking him. When he came, loads of cum oozed out from his limp dick and when she pulled out, he lay there like a wet cloth. Sweaty and breathing heavily. After a while, he got off the bed and went into the bathroom. While he was in there Tabatha pulled something out of her bag.

Matt crossed the short distance between the bathroom to the wall where his pants and underwear hung on a hook. He was about to reach for them when he felt Tabatha come up behind him.

“I have a surprise for you bitch and you better take it,” she whispered in his ear. At the same time, he felt two of her fingers work themselves in between his ass cheeks and her other hand pushing him forward against the wall. She used one foot to spread his legs a bit and then inserted the two fingers deep into his ass.

“Oh fuck, what is happening?” he moaned with pleasure.

“Remember the surprise I told you about? Here it is.”

He slowly turned enough so he could see her and between her legs was a large black dildo in front of her pussy. It was much bigger than the other, both in length and in girth. She gently pushed his face around so he was facing the wall.

Tabatha grabbed the pre-lubed dildo in her hand and began to work it into Matt’s anus. Luckily, he was still relaxed from being fucked so she felt him open up and pushed in.

Matt had his hands flat against the wall and pushed his ass out feeling like a whore. The dildo was much bigger than the other and he grunted for every inch that penetrated him. “Oh, oh, how much is in there?”

“Not even a quarter, bitch. Shut up and take it.”

And he did. When she began to slowly fuck him, he held his breath and closed his eyes. Being this stretched was yet again a new experience and he tried to relax as much as possible but he went up on his toes when he felt her skin against his. She was in now. Fucking him slowly her hands came around, tugging at his limp cock and pulling back the foreskin.

“Not much of a man now, are you? All limp and useless.”

“Oh god, I love it, do it faster, faster.”

She grabbed his hips and fucked him a bit faster. Even though she was beyond horny and loved the power she held over him, she was aware that he might get hurt so she was careful. The dildo began sliding back and forth with ease and Matt moaned and groaned.

A new sensation began and it felt like he needed to take a piss. Matt was confused since he had done that when they first arrived. The more she fucked him the more he had the need. Then suddenly it was gone and replaced by a new sensation. This one came from inside his ass, so warm and lovely. He moaned and pushed back against Tabatha as she continued to fuck him steadily. He began to recognize the sensation. It was the same as when he was about to come, but so much more intense. She had stopped touching him and when he looked down his cock hung limp between his legs with long strands of pre-cum hanging from it. A small puddle had formed on the floor. He moaned and said, “I need to come, please make me come.”

“Na, you can take it a bit longer.”

The more she fucked him the more intense the sensation. He realized what it must be. A prostate orgasm was building inside him. He was so excited to have that experience but then Tabatha took his cock in her hand and stroked it. All it took was a few times and he emptied his balls on the floor.

“Oh fuck, fuck, I was so close,” he moaned as she pulled out.

“Close? You just came.”

He turned around. She stood in front of him and to his delight he noted she didn’t wear any panties and her face was flushed. He had not seen her pussy until that moment and it looked tiny and was smoothly shaved. “Did you just come?”

She giggled and took off the strap-on holding it up to him. “I already came twice, thanks to this.”

There was another much smaller dildo attached to the harness and Matt realized she had been fucking herself while fucking him. “Oh wow, that’s so cool. Where did you get this from?”

“It's what I use with my girlfriend.”

They took a break from fucking for about a week and then they were at it again. Each time they would play the game of him being her bitch and they had a lot of fun together. Matt hoped every time she would give him his prostate orgasm but it never happened. They would try new positions and Matt liked riding her and missionary which she didn’t seem to be into. She loved fucking him doggy style where she was in control of everything.

His wife went to see her parents with the kids one weekend and he stayed behind because the AC repair man would come. He had planned a nice quiet weekend at home. His phone rang and it was Tabatha.

“Hey, what are you up to? Did your wife leave like you said?”

“Yes, early this morning. The AC guy just left.”

“You know that upcoming trip to Madrid you have?”

“Yeah, what about it?”

“Veronica and I thought about inviting you for dinner before you left and today seemed to be perfect.”

“Veronica as in your girlfriend?”

“Yeah, you have never met and we thought it would be nice if you did.”

“Sure, send me your location and time and I’ll see you then.”

This was a big deal. Tabatha had always been a bit secretive about her girlfriends. Even though they had known each other for many years he had never met one. He did know that Tabatha had turned to women in her mid-twenties as a bisexual but over the years she had stopped dating men and kept to women. Veronica and she had been together for a few years now. She was a bit younger and worked in a bank. That’s all he knew about her.

When he parked his car outside the little white house in a suburb across the canal Tabatha was outside. A small dog sat by her side and when Matt got out it ran to him and licked his hand.

“Welcome, please come in,” Tabatha said.

The house was neat, with a living room that had French doors to a backyard where a table and four chairs sat under a gigantic parasol. There was a small lawn with flowers against the wall that circulated the house.

“Hi and welcome,” said a voice and Matt turned to his right. In the small kitchen stood a woman who looked to be in her thirties, quite tall and beautiful. Her long black hair sat in a ponytail high up and she wore a white dress that ended above her knees.

“Matt, this is Veronica. Veronica this is my boss Matt.”

They shook hands and Veronica took out three beers from the fridge and handed them out. “Here is to new friends,” she said.

Matt felt something in the air, there was a tension in it but he couldn’t quite place it. Tabatha and Veronica gave each other looks and for a second Veronica smiled a little and gave Tabatha what looked like a nod. Matt was sure there was more behind that nod but didn’t want to pry so he let it go and he and Tabatha went outside and sat down.

“She is very pretty,” he said.

“Thanks, she is the love of my life.”

“I’m sorry for the question but is she bisexual or lesbian?”

Tabatha laughed. “That’s not a question you ask, Matt. But since it’s you the answer is she is lesbian. She has never been with a man in her life.”

Matt whistled. “Wow, I never met someone like that.”

It was Tabatha’s turn to laugh. “Why would you? You don’t hang out in gay circles, do you? But I can tell you this much, where we used to work when I was young, there were several hard-core lesbians.”

“I had no clue.”

“I know, sometimes you are completely clueless and that’s what makes you so much fun.”

For dinner Veronica served wine and Matt noticed she was drinking more than Tabatha and him, as if she was nervous about something. The food which was a fish dish was delicious and when it was over Veronica opened another bottle and they went outside. The sun was setting and a cool breeze touched their skin. Veronica was by now quite giggly and moved from her chair to Tabatha’s lap. Matt felt something was going on and since he had a few too many himself he said, “What’s going on with you two? Veronica is nervous and can’t sit still.”

Tabatha helped Veronica onto her lap and then said, “I asked her if she would like to try cock and after a few days of thinking about it she said yes.”

Matt was very surprised and said, “If she is lesbian, why would she do that?”

“Because I’m curious. I’m thirty-eight years old and I have always been attracted to women but, after Tabatha told me about your experiences, I realized I could give it a try, just for the fun of it.”

Matt felt how his face turned red and he said, “Tabatha, I thought this was between you and me.” He was very disappointed in his friend.

“I know, but Veronica noticed something in me when we were together and after she asked me about it many times, I had to tell her. I’m sorry.”

“Well, it's done now. No way to change that;” said Matt with disappointment. He drank from his wine.

“Look, after what Tabatha told me I realized that one can have fun sexually without being in love. I come from a deeply religious family who rejected me because they thought love could only be between a man and a woman. I thought that my entire life until now. I’m curious about men, how they work, and what the dick is all about. I would never and I could never fall in love with one, but I would like to have fun. Just like you and Tabatha.”

Veronica was drunk, but her words were honest, thought Matt. “Okay and what will you do about it?”

Veronica giggled. “If Tabatha is comfortable with you, so am I. I want to play with your cock and see what’s it like.”

She was a good-looking woman and Matt was still a man and his dick began to move in his pants. He adjusted it a little hoping the women wouldn’t notice.

“Ah, and there you have it. You have an erection. See, I told you, Veronica. Men are easy. As soon as they think they will have sex they go hard. C’mon Matt. Show it to her.”

Matt gladly opened his shorts and pulled them down and his cock popped out. He felt comfortable with Tabatha and the thought of being fucked again made him not care about Veronica’s presence. He stood up and said, “Here you go, Veronica.”

“Go on, go and touch it and kiss it,” said Tabatha sliding Veronica off her lap. Veronica got up and walked around the table without taking her eyes off Matt’s cock. She gently pushed him back into his chair and knelt before him. She took him in her hand and stroked him. “Does this feel good?”

“Mm, it does. You can suck it if you want.”

“Fuck, it’s so hard. I never thought a dick was this hard and so soft at the same time. She opened her mouth and put the head just past her lips and sucked on it. “So, so very soft,” she said before she took all of him.

Tabatha watched them for a moment to make sure Veronica didn’t change her mind and then went to their bedroom where she got the two strap-ons. She knew what Matt wanted and he sure as fuck was going to get it.

Veronica liked sucking. It was different from eating pussy, that was for sure. The dick was so hard and after a while a liquid came out that was sweet and she sucked it out of the tip.

“Here we go, time for some fucking. Put this on Veronica, you are first up,” she gave Veronica the smaller strap-on and put on the bigger one. Matt sat with a big grin on his face. He was in heaven.

“C’mon, let’s go to the sofa. I locked the dog in the bedroom or he will bark.” Tabatha said and took Matt by the hand. She gently bent him over the armrest and proceeded to lube up his ass and Veronica’s strap-on. “There you go, all set. Push it in gently and if he asks you to stop you do it.” Veronica nodded and stepped closer to Matt who had his legs wide apart exposing his anus.

Veronica was nervous, not only didn’t she want to hurt him, but she had never done something like this. It was different from fucking Tabatha but at the same time similar. She put the tip to his anus and began to push. First, nothing happened so she added some pressure and he began to open up for her. She pushed a bit harder and Matt grunted.

“Are you okay?” she asked.

“Yeah, I’m fine. It's when the head slides in it hurts a little, but I’m fine.”

She pushed in further and he opened up more. Then she was balls deep. His anus was tight around the shaft of the toy. His dick was hanging between the armrest and his groins so she played a little with his balls before beginning to thrust.

“Oh, fuck, yeah, that is so good. Keep going Veronica, don’t stop.”

Tabatha was doing something she usually didn’t do when with Matt and that was, she was fingering herself. She was so horny and she just couldn’t help herself. It was beautiful watching her girlfriend fucking her friend.

“Oh god, yes, I’m feeling it, yes, please make me come,” moaned Matt and Veronica looked at Tabatha confused.

“He means he almost had a prostate orgasm, just keep fucking him.”

Matt was in heaven. He was sure he would finally reach his goal, coming from a rubber dick up his ass. He could feel the pre-cum running out of his cock and he was loving it.

Tabatha moved closer to Veronica. “Pull out, I’m taking over. You sit on the sofa. Matt, I’m going to turn you so I fuck you against the wall with Veronica sitting under you. She will have your cock in her mouth.”

After a bit of moving around Matt and Veronica were in position and Tabatha penetrated her friend with the larger dildo. It slid in surprisingly easily and she was fucking him deeply. She made sure her thrust was even and had a steady rhythm. Matt moaned and pushed back onto her.

Veronica looked at the limp dick just above her and then put it in her mouth after pulling back the foreskin. It felt weird she thought. When it was hard, she had loved it but this flaccid thing did nothing for her. She did suck the pre-cum that came out and waited for Tabatha to tell her what to do.

“Oh, oh, yes, yes, I think I’m coming, oh fuck, oh fuck,” moaned Matt as his legs began to shake.

Tabatha kept on fucking him and caressing his ass and back. She loved having him like this. She had the power and now she was going to give him a great gift.

Suddenly Matt’s cockhead grew in Veronica’s mouth and she realized something was going on. It was just the head that had grown, the rest remained flaccid like before. Then it came. She had thought he would squirt like in the porn clips she had seen but instead, the cum came as hot lava and a lot of it. Matt moaned and shook as it kept flowing from his limp cock, filling Veronica's mouth and she began to moan.

“Honey, you have to swallow,” said Tabatha hearing her moaning.

Veronica did but there was more and more of the hot liquid filling her mouth. She didn’t count how many times she had to swallow but a lot more than she had expected.

“Oh fuck, oh god,” moaned Matt and moved backward, his dick slipping out of Veronica's mouth. Tabatha gently pulled out and Matt almost fell onto the sofa. His face was red and wet from sweat.

“How was that?” asked Tabatha.

“Amazing, it was incredible. The orgasm was so much longer than usual.”

Veronica wiped some cum from her chin and boobs. “I have no idea how much a guy normally comes, but it was a shit load.”

“Did you like it?” he said.

“I loved the feeling of your cock pulsating and coming but the taste, not so much.”

Tabatha laughed. “At least you have tried cock and at the same time help my friend to an amazing orgasm. I say it’s a win-win for everyone.”

A couple of days later Tabatha took Matt to the airport for his flight to Madrid where he was going to attend a convention. They hugged at the security check.

“I’ll miss your ass bitch, bring it back soon,” she said after they let go of each other.

Matt laughed. He sure would miss their escapes but it was only for a week and then they could go back to them.

The convention was interesting and Matt took a lot of notes and mingled with others in the industry. On Friday there was a party and he got pretty drunk and narrowly escaped one of the women who was there from Germany to go with him to his room. She was hot enough but Matt didn’t want to. Someone might see them and the word would get out.

Since he had a few days to spare before going back to Panama he had called an old friend who lived in Marbella to see if he could pop by and they could catch up. His friend had said yes and that he was looking forward to seeing Matt again.

When he stood in line to board the flight to Marbella early on Saturday morning, he was blurry-eyed and had a pounding headache from the whiskey the previous night. He popped a couple of pain pills and sipped on his black coffee. The flight would be full and he wasn't looking forward to it. Behind him was a family with a screaming baby and a nagging toddler. He sighed and drank some more coffee.

A woman came walking towards the line and Matt’s attention turned to her. She was taller than him which didn’t say much since he was short for being a man. She wore a long skirt with a hippie feel to it and black boots. On top, she had a white T-shirt that ended below her boobs but showed off the piercing in her belly button. He put her age somewhere between twenty-five and thirty. She had long black hair that she played with using her left hand while the right held a bottle of water she was drinking from. She stopped at a couple in the line a few people in front of Matt and spoke to them in Spanish. He heard she had a deep voice and then, looking at her closely he realizes she was a transwoman. Not a man in a dress. Her skin looked soft and her face had that glow to it that some women have. But there was an Adam apple and her hands were quite large. Matt was mesmerized by her. This was not some hooker in a casino. This was a normal woman, but a transwoman.

The flight was called and everyone in the line began shuffling forward holding their passport and boarding card up to the flight attendants to check. Once inside the plane, he located his seat which was 15B, aisle seat up front. As he got closer, he noted that someone was sitting in the seat next to his but had their head down. When the person looked up it was the girl from the line. Matt felt sweat running down his arms and he became nervous. He wasn’t sure why but he was. Once at his seat he put his bag in the bin above and sat down.

“Hi, I’m Isabell,” she said holding out her hand.

Matt took it and it was so soft in his. “Matt, nice to meet you.”

“Is this your first time in Marbella?”

“Yes, I’m seeing a friend.”

“I’m from there and have lived in Marbella all my life. It’s a wonderful city with many things to do.”

Matt was still nervous and stared straight ahead at the flight attendant who had begun her security speech. Isabell stopped talking and looked out the window. She smelt nice, thought Matt still looking straight ahead. It was a soft, rather fruity smell but not overwhelming like some could be. Matt relaxed in his chair and dared a glance over at Isabell who was still looking out the window. Her skin was flawless and she had small ears which he thought was sexy for some unknown reason. Her bare arm was close to his, resting on the armrest. She had a few rings on her fingers and two earrings in the ear closest to him.

She turned towards him and smiled. Her teeth were white like in the ad for toothpaste. “Where does your friend live?”

“Not sure. He is supposed to pick me up at the airport. Have you been to see friends in Madrid?”

“Yes, but I also did a photo shoot.”

“Oh, you are a model?”

“Just part-time. It gets me out of Marbella every once in a while, and the extra money is always helpful. Where are you from?”

“I live in Panama but originally I’m from Germany.”

“Oh my, how come you ended up in Panama?”

“Love, I guess. I met my wife at university in the States and we moved to her home country. Much warmer and nicer than Germany.”

Isabell laughed and he adored the sound of it. “I can understand that. I went to visit a friend in Norway a few years ago and I was freezing the entire time.”

“What do you do for a living?”

“I run a café down by the port in Marbella.”

“Oh, at the famous Puerto Banus?”

“No, in the city, the small port. I prefer that to Puerto Banus. It’s over prized and the people that go there are mostly rich assholes and loads of hookers.”

“Really?”

“Yes, my advice. Stay away from there. You should come and visit my place instead if you have the time.”

The flight took off and they spent the short flight talking about Isabell's sisters and brothers about Matt's family and work. Never did the fact that she was a transgirl come up. She would often hold his hand, or touch his arm as they spoke. Matt didn’t mind it at all, it felt rather good. When the flight attendant called out that they would soon be landing Isabell gave him her phone number and told him to call if he had time.

Once the fasten seatbelt sign was turned off the passengers began to shuffle off the flight. Matt headed for the closest bathroom after saying goodbye to Isabell. When he was about to wash his hands, his phone rang.

“Yeah?”

“Man, it's Mike. I’m so sorry. My car broke down and I’m still in Granada. There is no way I can make it back for the weekend. I’m so sorry. I tried to call earlier but I guess you were on the flight.”

“Oh, man, that sucks. I was looking forward to hang out and have a few beers.”

“I know. I got to go, but have a good time without me.”

After hanging up Matt went to find a taxi and took one to his hotel. It was a fifty-minute drive from the airport to Marbella and it was a beautiful ride. On one side was the sea and on the other the mountains

Once he had checked into his hotel which was in the old town of Marbella on a small street with restaurants and bars lined with orange trees, he sent a text message to his wife and then an email to Tabatha where he told her about Isabell. His wife was first to answer telling him she was sorry he couldn’t meet his friend but have a good time anyway.

A few minutes later the email from Tabatha arrived. It was short and to the point. Suck her dick, I dare you too, and take a photo.

Fuck, I’m too scared, what happens if she says no, I’ll be so embarrassed.

The answer came back much quicker than the first.

 Don’t be, just ask her out and see what happens. I’m sure she will say yes after what you told me about her.

He texted Isabella asking if she would like to have dinner with him. She answered saying that was fine and to meet her at seven. Matt changed into shorts for a stroll along the small streets and had a glass of wine on the way. He enjoyed the walk and when he came back to the hotel it was time to shower and change.

Isabell was waiting for him when he arrived at the crossing of two of the small streets. She stood under an orange tree and looked adorable. She had changed into a white summer dress with thin straps over her shoulders. She wore just enough makeup to make her look sexy without being vulgar.

“Hi, handsome,” she said and kissed him on each cheek.

“You look very pretty,” he said.

She spun around. “Thank you. I thought we could go down to the port and have wine and tapas?”

She took him under the arm and they made their way the few blocks to the port. At first, Matt felt a little uncomfortable, being sure that people would see that Isabell was a man, but no one gave them two looks, not even one look. Once they arrived, they walked along the water until Isabell stopped in front of a bar. She spoke to one of the waiters and then asked Matt to sit down at a table away from the street.

“The street vendors can be a pain in the ass, that’s why I prefer to sit here.”

A few minutes later the waiter put down two glasses of white wine and two plates. One had small fish filets and the other had potatoes with some dressing.

“That’s Patatas bravas, quite spicy and those are herring filets in olive oil. Very tasty.”

Matt tried a bit of both and was pleased. “It’s good and the wine is just amazing.”

“What happened to your friend?’ she asked after they had finished the food.

“He had car trouble and didn’t make it back in time.”

“Oh, that’s too bad. Now you are stuck with me,” she said and giggled.

“It could be worse.”

She put a hand on his and said, “I like you. Let’s order something else to eat.”

And so the evening went on. More wine, more tapas until the sun went down close to nine. Matt said he would walk Isabell home, being the gentleman, he was. She said she didn’t live far away. Since they were far from sober the walk took almost twenty minutes before Isabell stopped.

“I live here, on the second floor.”

Matt looked up at the little Juliett balcony she pointed at. The street looked like the one where his hotel was and he realized he was closer to it than he had thought.

“I must say I had a wonderful evening, and I hope we can meet tomorrow if you like,” he said.

She looked down at him and smiled. “I thought you might want to come up for one more drink. It’s not like you have to work tomorrow.”

Matt became nervous. One thing was to be in a public place with her but alone, in her apartment. He remembered what Tabatha had said and that made him even more nervous.

“Are you sure, I don’t want to impose?” he said.

“I was the one asking, so no, you are not imposing. Come on.”

The apartment was painted white and was small. The living room had a two-seat sofa, and a low glass table, and in front was the balcony.

“Have a seat. I’ll get you some white wine. It's not good to mix after having so much as we have.”

He sat down and she was back quickly with a glass. Then she went to what turned out to be the bathroom. Matt drank from the wine and considered his next move. He hadn’t seduced a woman since before he met his wife so he had no idea how to go about it. Oh shit, he thought. Kiss her? He would be kissing a man. Oh fuck, this was complicated, he thought.

The door opened and Isabell came out. She grabbed a glass from the kitchen and sat down next to him. “Here we are, just you and me Matt.”

There was a silence and the tension was so high Matt thought he could hear a crackle in the air. “I guess so.”

More silence. Isabell drank from her glass; Matt did the same. She put it down and stood up. Turning to Matt she pulled up her white dress. “How do you feel about this? I know you know I’m a transgirl. How do you feel about me now?”

Matt was frozen in place. He just stared at her cock that hung limp between her legs. She was shaved and her balls were hardly visible behind the shaft. He slowly lifted his eyes and they made contact with hers. “I..I don’t know what to say.”

“It’s ok if you want to touch it.”

Matt looked back at the cock and if he wasn’t mistaken it was slowly growing in front of him. The cockhead began to peek out from its hoodie. He slowly reached out and ran a finger along the top. The skin was warm and soft to his touch. It kept on growing and quite a bit faster until it was fully erect.

“Does it make you uncomfortable?” she said in a whisper.

It was completely dark outside and Isabell hadn’t put on any lights when they came in so the apartment was also quite dark.

“No, it doesn’t.”

“Did you like touching it?”

“It felt weird.”

“Have you ever touched one before?”

“No,” which wasn’t a lie since a dildo is not a real cock.

“The way you are looking at it makes me think you want to suck it?”

“What? I’m not looking at it in any special kind of way.”

She giggled and the cock bounced a little. “Your mouth formed an O and you were staring at it. Go on, try it.”

Matt knew the moment he saw her cock that he would suck it, there was no question about it. Sucking on a dildo pretending it was a dick was one thing. Sucking on a real meat and muscle cock with balls, even though they were small was something very different.

Isabell grabbed the base of the dick and moved half a step forward pointing it at Matt's mouth. “Go on, open up. I know you want it.”

Matt closed his eyes and opened his mouth. The soft skin of the head slid over his lips and then it filled his mouth with its warmth. He opened his eyes and looked up at her.

“There you go, open a bit more, just like that. Doesn’t it feel good and sexy?”

He couldn’t speak but managed to make some kind of positive sound before she pushed it further back until it touched the back of his throat and he had a gag reflex.

She giggled. “Oh my, are you sure you haven’t done this before? Most men just lick it a little, but you are taking it all the way. Oh fuck, I love how your throat tightens around the head. Just suck it the way you like it.”

Matt took the shaft in his hand and stroked it while he sucked on the head and licked the point just under it. Isabell had eye contact with him all the time and she moaned, “Oh, yeah, just like that, suck it, suck it, oh fuck you are good.”

He loved how the cock filled his mouth and how incredibly hard it was. It did feel strange that she had almost no balls, just some skin where they should be.

“Oh, oh, easy, easy, or I’ll come,” she said and slowly pulled out from his mouth, making it feel empty.

She smiled at him. “Did you like that?”

“Yeah, it was strange but so exciting.”

“Just be more careful with your teeth. You need to open your mouth more. Here we go.”

She fed him his cock again and Matt did what she had said. He was so hard, and he knew he was dripping pre-cum and he wanted her to touch him. She put a hand on his head and began to thrust gently.

“Oh, oh, time for a break. Stand up,” she said.

He did and she took off his shirt, unbuttoned his pants, and pulled them and his shorts down exposing his cock. She took it in her hand and gently stroked it while leaning in. Their lips touched and when they did, Matt pulled back.

“What’s wrong?”

“I..I.. I’m not sure. I feel stupid now.” He sure did, she could see in her eyes she was hurt. At that moment his lizard brain had remembered she had at one time been a man, well, if you considered his dick she still was.

“Do you want to stop?” she asked quietly, obviously disappointed.

He stepped closer and held her in his arms. He looked up at her and they kissed softly. He felt Isabell’s cock grow hard again against his stomach and his against hers. It was an odd but exciting feeling. She began to stroke him and him her while they kissed. Matt felt how she began to move backward, taking him with her and they ended up in her bedroom

“Leave the lights off,” he whispered.

“Do you want me inside you or do you want to fuck me, Matt?”

Matt pretended to deliberate the options but as soon as they had moved toward the bedroom, he knew what he wanted. “Maybe you fuck me first? If I come, I might chicken out.”

She laughed and had him sit on the bed while she opened a drawer and took out a condom and a tube of lubricant. She put on the condom and then spread plenty of lube on her cock.

“Get on all four and breathe slowly,” she said.

When he was in position her finger penetrated his anus rather quickly and he moaned.

“Shh, honey, just relax. You are doing great.”

A few minutes later Matt felt another finger and he grunted. “Oh, fuck.”

“You are such a soldier not whining or bitching. I’m going to start penetrating you now. Push back like if you were going to the toilet.”

Matt knew exactly what to do from his experiences with Tabatha but for some reason, he didn’t want Isabell to know. He wanted her to think it was his first time. He relaxed as much as he could and when he felt the tip of her cock he began to push back and immediately he opened up for her. He grunted as her cock head slid in. It was larger than the toys he was used to but once inside it felt fine.

“Matt, you are doing great. I could swear you have done this before.”

“Nope, never. Maybe I’m just naturally gifted?”

She laughed while pushing in further. “No, my dear, the first time, almost everyone squeals like a pig and moans about the pain.”

He felt her hands on his hips as she began to slowly fuck him. It was such an intense and beautiful feeling having her cock slide in all the way and then slowly out again. Each time it slid over his prostate he would moan with pleasure. The cock was hard but at the same time soft so it molded itself to him much more than the toys had. His cock was oozing pre-cum by now and Isabell cupped his balls and played with them.

“Honey, I want to fuck you in a missionary and watch your eyes,” she said.

She pulled out and he rolled over on his back with his legs apart. To Matt, this was a different sensation. Tabatha had mostly fucked him kneeling between his legs. He guessed lying on top too often became too personal for her.

“Here I come,” she whispered in his ear. Matt moaned as she penetrated him but it didn’t hurt at all. He wrapped his arms and legs around her body and held her tight as she fucked him. They kissed deeply, holding each other close and as Isabell began to reach her orgasm she moaned in his ear, “Oh, oh, I’m so close. Your ass is driving me insane with pleasure.”

Matt squeezed his ass cheeks and Isabell let out a few grunts and Matt as well when he felt her cock twitch and empty inside him. He didn’t know how much cum there would be considering her tiny balls but what felt awesome was how the cock twitched.

She pulled out and lay down between his legs and began to suck his dick. She was going at it viciously, sucking and stroking like he had never experienced before. When his body tensed, she took him deep and he emptied in her mouth.

Matt lay on the bed with his mind going in thousands of directions. Tabatha fucking him was good, Isabell fucking him was a completely different level of pleasure. He wasn’t in a mood to fuck her at all. He was happy where he was and didn’t need or want to do anymore.

“How are you feeling?” she asked and sat down on the bed next to him placing her hand on his chest.

“Fine, great actually. That was something amazing.”

“Yeah, you liked that, being fucked in the ass?”

“Mm, I did. It's not better than fucking a pussy its just different being fucked.”

“Do you want to fuck me?” her hand slowly moved down to his cock and she was stroking it but nothing happened.

“Nah, I’m fine like this. If that’s ok with you?”

She let go of his dick. “Do you want to take a shower?”

He got up and went to the bathroom. When he came back out again Isabell was sleeping. She lay on her back, one leg cocked to the side. Her beautiful cock against her thigh. Matt gently kissed it before getting dressed and sneaking out into the night.

Tabatha got his message and it read. Been fucked and sucked cock. Amazing!

She smiled and typed back. Better than me?”

Different. Still miss you and our toys. I’m sorry I couldn’t get the photo of me sucking cock. It was just too good to stop in the middle.

She sent him a smiley and put the phone down. She was happy Matt had done what he wanted. She had always thought men and women should explore sex and try new things. Just because Matt had sucked dick and been fucked didn’t mean he loved his family less or that he would leave them. He had only explored his fantasies, which was great.