A Player's Romance

It was lunchtime on a Tuesday, I was heading to a café in the city to meet up with my girlfriend Trish. We have been together for about three months now, and I was enjoying our relationship so far, more than I thought I would.

A bit of context here, my name is Mike Oliveira and I'm twenty-nine years old. I work as a Sales Rep in the city, I'm divorced and while not rich, I'm doing fine. Trish, or Patricia which she hates being called, is a twenty-five year old divorcee herself, she a 5'7 brunette with lovely big tits and shapely legs, It was both of those features that attracted me to her at the club when we first met. Trish also works close by as a travel consultant, which she gets to enjoy the perk of occasionally traveling a bit for free.

"Hey gorgeous, love the dress you're wearing today, it matches your lovely blue eyes."

"Could you be any smoother Mike?"

"Hey, it's in my job description."

Trish just shook her head at my obvious platitudes and went back to perusing the menu.

"Phil asked if we would be interested in going out to dinner Thursday night, what do you think?"

"What just the three of us?" Trish enquired.

"Nah, he has a date. He's probably trying to show her what nice friends he has so he can get into her pants quicker."

"You two are such players, I wouldn't be surprised if you try and get into them as well."

"That depends."

"On...?"

"If you are joining us, we haven't had a foursome yet."

Trish again shook her head but smiled this time, then stepped up to the counter to place her lunch order.

I have to add here that I never thought that three months after meeting Trish, well, that we would still be seeing each other much less in a relationship. My intentions were to fuck her a few times, then move onto the next woman that caught my eye. She wasn't lying when she called me a player, I have successfully been picking up women since I was in my late teens. Even while I was married to my first wife, I kept playing the field and sleeping with a new woman every week almost. So much so that she found out and we got divorced.

Trish on the other hand was married at twenty, a marriage that lasted for a few years to a man that cheated on her repeatedly. So, you're probably wondering why in the hell would she want to be in a relationship with a guy like me that cannot keep it in his pants? I'm not sure, she has dated a number of guys since she was divorced, so maybe she is just playing the field now too.

We found a table to sit at and began to eat or lunch. I quietly sipped on my juice as I looked at Trish's pretty face. She is smart, interesting and funny, not to mention great in bed. It is easy to want to spend time with her, what I wasn't sure about was why she wanted to spend time with me outside of the bedroom? Why are we here at this café three months after what should have been a few fun rolls in the hay?

"Can I ask you something Trish, about us?"

"You're not going to ask me to move in, are you?"

"No, that's not my question."

"Okay then, you had me worried for a moment."

"Why are we here?"

She looked at me puzzled, it was not about where we were sitting, but about us, our relationship.

"You're not happy dating me Mike?"

"Of course I'm happy dating you, I'm just trying to figure out why we are dating at all?"

"What do you mean?"

"You knew who I was the moment I started chatting you up that night. You also knew what I was after and you gave it to me just a few hours later."

"It was a good night, I enjoyed myself. So, what's your problem exactly?"

"Why didn't we leave it at that? Why do I still want to see you every day, and why do you let me?"

Trish looked at me while taking another mouthful of her salad, just looking into my eyes like she was trying to figure that question out herself.

"I like you Mike, I enjoy spending time with you. I'll admit that I only ever intended on fucking you a couple of times at first as well. I'm not sure why we are still here together. Neither of us has stopped seeing other people these last three months. Maybe it's just that we've been honest about what we're doing, where we're at."

"And where is it that we're at?"

"Look Mike, after my divorce I decided I wasn't going to be the victim anymore. Over the last year or so I have dated several men and slept with all of them. And I will continue to see other guys. I'm going to have my fun too."

"I get that, and I'm happy about that too, believe me. But are you saying that because we both enjoy fucking other people, that is why we are here right now?"

"Kind of, we can be more honest with each other. I don't have to justify myself with you, and I like that. I don't get upset when you pick up some pretty young thing at the club, nor do you get upset when I go out on dates with other guys. So, we can just be us."

I nodded and bit into my bagel. I never contemplated that after my divorce I would actually want to be with someone in a relationship. I'd been enjoying myself, fucking a lot of sexy women. Some were single, some had boyfriends, more than a few were married. It didn't bother me, I enjoyed fucking them all, and they enjoyed me fucking them. Nearly all came back for more. A part of the thrill is getting them to want to be fucked, the chase if you will.

The married women and the single girls were less fun in that aspect, they are too easy. Especially the young naïve girls you could sometimes meet, still looking for that handsome prince charming mixed with a bit of a bad boy persona. They want to believe anything I tell them, too caught up in my good looks and confident charisma, it's like taking candy from a baby. For the married women it's a different approach, they want the sexy confident guy who can keep secrets.

It's the women with boyfriends I enjoyed chasing the most, watching how they struggle with wanting me while trying to stay loyal to their boyfriends. It makes the sex more fun because they are usually caught up in their emotions more, with both the thrill and guilt of cheating. It makes the sex more passionate, more intense. Those are the women that cum the hardest when I fuck them with my thick cock.

With Trish, she didn't fit into any of those categories, she was single but definitely not naïve. The sex was also surprisingly good. Some people you just click with a little easier in the bedroom, and that was us. If you're wondering why I sleep with so many women, well, It's because I can. I'm sorry for those guys that aren't good looking, or that don't have a clue about women, either thinking of them as sweet princesses or as total sluts. Those guys just make my job easier.

It was Thursday night when I picked up Trish in front of her apartment, she looked great in a little black dress that struggled to stop her large breasts from falling out. She was going to turn a lot of heads tonight.

"Hey handsome, good to see you on time for once."

"Hi Trish, you look great. I can't wait to take that dress off you later."

"Who said you'd be the one undressing me tonight?" Trish replied with a cheeky smile.

"So, we're doing the foursome tonight then?"

"No, I might just like one of the dashing waiters at the restaurant and have to take care of myself."

"As long as I can join in we're all good." And gave Trish a wink as I drove us to the restaurant to meet Phil and his date.

We got to the restaurant and found Phil's table, he was there with a sexy young blonde named Bree. Phil and I used to work together but have remained friends since. We enjoyed catching up for beers, going to the gym, or going to clubs together to pick up women and sharing some on occasion. Like me, Phil had little trouble getting women into his bed, he always joked he had more trouble trying to get them out of his bed then in.

After introductions and ordering we settled in for a nice glass of wine.

"So, what do you do Bree?" Trish asked.

"Oh, I'm a senior majoring in economics."

"You're still in college? How did you meet up with Phil?"

"He knew one of my friends." Bree responded, looking a little sheepish.

It was obvious that Phil had already fucked her friend, and well, women talk. Bree was obviously keen to try out what her friend had already sampled.

"Are you looking to make an honest man out of Phil then Bree?"

"Oh god no, I already have a boyfriend." Bree giggled at giving this revelation.

"Are you two serious? You and your boyfriend?" Trish was enjoying figuring out Bree I think.

"Yeah, we will probably get married after we graduate. There's no rush just yet, I still want to enjoy myself a bit first."

"And does your boyfriend know you're here tonight? With Phil?"

"No way, he would have a heart attack if he knew I was here."

Phil then interjected before Trish gave Bree any second thoughts.

"So Trish, why are still seeing this lout? I thought you would have wised up by now?"

"I don't know Phil, maybe I just love his big cock too much to let him go."

"Hey. Come on guys, you are going to scare Bree with all this talk." I interjected.

"No, it's okay Mike, I like hearing about big cocks." Bree added with a sexy giggle.

"Well, you just wait and see what I got for you for dessert." Phil responded as he gave her a little kiss.

Trish then leaned over to me and whispered in my ear.

"Were you joking about that foursome earlier? I might just be interested if you're serious."

Well, this was a development. Trish chatting to the naughty young Bree has stoked her fire.

"I'm sure I can arrange something with Phil, we can go back to his place after dinner if you like."

Trish nodded back to me, as our meals arrived.

We arrived at Phil's place or should that be palace. A definite player's palace. The decorations and furniture seemed like they were straight out of a high-class brothel, even down to the oversized jacuzzi in the main bedroom. And Phil got good use out of it too, there was no end to the line of woman that wanted to sample his super fit body and large cock.

Trish and I took one of the love seats in the lounge room and Bree settled in on the other while Phil went into the kitchen to make us some strong drinks to get us in the right mood. Trish didn't waste time and leaned in and started a deep wet kiss with me.

"Ooh that looks so sexy" Bree commented.

Trish slowly broke our kiss and looked over to Bree.

"Why don't you come over here and try it for yourself."

Bree giggled then got up and sauntered over to our love seat, kneeling in between Trish and myself. Trish then surprised me again by leaning into Bree and starting a long wet kiss with her.

"Hot damn, you guys started without me." As Phil walked over giving us our drinks.

Phil then knelt on the floor behind Bree and started to fondle her breasts, feeling down her sides to her ass then back up again as Bree began to kiss Trish once more.

I reached under Trish's little black dress and began to gently rub her pussy, I could already feel it's dampness on the outside of her thong. I slipped the thong to the side and inserted a finger which drew a quick breath from Trish.

Bree began to moan and broke the sensuous kiss she was sharing with Trish, I knew that Phil had just like me, began to insert his fingers into Bree's wet little pussy.

"I want you to undo his pants for me Bree." Trish stated in a low calm tone.

Bree was smiling at Trish as she moved her hands over to my pants and began unbuckling.

"I hope you don't mind sharing Phil?" We had shared woman many times, but it was always good to ask.

"As long as we are all sharing." Phil then looked over at Trish and gave her a wink.

"Of course, I always wondered what you were hiding from me Phil." Trish smiled back.

"Well why don't you find out then Trish." As Phil got to his feet and moved around to the side of the loveseat so that Trish like Bree could start unwrapping her present.

I raised my hips so that Bree could pull my pants down, but when she did, she had pulled my boxers down with them and my semi-hard cock flopped out for all to see.

"Oh my, you're very big Mike." Bree said a little surprised.

"Just wait until he gets hard." Trish added.

Without waiting Bree grabbed my cock and leaned forward to put it straight in her mouth.

"Oh, fuck yeah Bree, you're such a naughty little girl, aren't you?" I encouraged her.

Bree didn't answer that, she just looked up into my eyes as she continued to suck on my growing cock. Then I heard Phil groan and looked at Trish beside me to see that Phil's large cock was already in her mouth.

"Well Phil, this is how every good dinner date should end."

"Absolutely Mike, abso-fucking-lutely!"

My cock was now hard, and Bree was fond of licking it up and down and staring at it a little, I was assuming she had not seen a large cock before.

"How do you like that cock Bree? Is it as big as you're boyfriends?" I asked teasingly.

"It's way bigger, I love it. Look, I can't even put my hand around it." God, I love these nasty young girls.

Bree went back to sucking my cock, as Phil then moved back around behind her, raising her dress and pulling her panties down, then without waiting, he started to slowly push his cock inside of Bree.

She groaned loudly on my cock, then withdrew with her eyes closed and that expression on her face that was a mixture of pleasure and pain.

Trish then stood and placed her leg over me, pulling her dress up as she lowered her pussy onto my cock. She was facing away from me, and as she slowly slid down my cock Bree would have had the perfect of view of us right in front of her.

Again, Bree pleasantly surprised us as she leaned forward and began to lick both my balls, and then Trish's clit with her tongue as Phil began to thrust deeper into her.

Before long Bree was having her first orgasm of the evening, and it would be the first of many. Trish was not far behind her, as she lay back across me and turned her head so we could kiss as she continued to ride my cock, that with Bree paying attention to her clit was enough to send her into her first for the evening.

"Why don't we take this to the bedroom guys?" Asked Phil.

With that we all stood and made our way there, quickly downing our drinks on the way.

"I want you two to sit on the edge of the bed." Commanded Trish, and we did as we were instructed.

Trish and Bree then knelt in front of myself and Phil respectively and began to suck our cocks again. After a few minutes, Bree followed Trish's lead as both of them hopped up on top of us to begin fucking us in the cowgirl position. Trish lifted her dress completely off as I was looking up to those magnificent tits as they sprung free above me. I began to fondle them as Trish began to grind down on me.

Trish then leaned forward and gave me a deep sensual kiss as she continued to grind on my cock. She then whispered to me.

"This is so much fun, I should have tried this before."

"We're just getting started, just wait and see how you feel after we have both fucked you senseless."

Trish was still facing me, looking into my eyes and smiling, then leaned in and kissed me again. Goddamn I thought to myself, this is the first woman I truly have feelings for since my ex-wife. Not jealous possessive feelings like some idiot guys, but an actual connection with her as a person. I really was enjoying being with Trish.

After a few minutes, Trish looked over to Bree riding on top of Phil's big cock, she was getting close to cumming again. Trish then leaned over and they both kissed, this seemed to inspire Bree to her second orgasm of the night. With her cumming, Trish then came herself, turned on by Bree no doubt.

"Let's swap Bree, I want to try out Phil for a bit."

Bree looked into my eyes and smiled with a sexy grin before hopping off Phil and moving across on to my cock. Her pussy was tight, though she had not yet learned to milk a cock with her vagina muscles like Trish did, the tightness itself was great to feel. She closed her eyes and she pushed down on me to take all of my cock inside.

"God this is so naughty, fucking two big cocks one after the other." Bree said to no-one in particular.

"You won't get to meet too many guys like these two to fuck in your life Bree, you should enjoy it tonight." Trish added as she began to ride Phil with more intensity.

"What do you mean Trish? You can fuck us whenever you want, not just tonight. I will happily fuck Bree as many times as she needs." Phil responded as he groped Trish's big tits while she rode him hard.

"But I'm not married and I'm with Mike. Bree will go back to her boyfriend. She needs to cum as many times as she can while she's here."

"True, but you're forgetting the part where I don't care if she has a boyfriend, I will still fuck her whenever she wants me to." Phil looked over and winked at Bree while she was now bouncing up and down on my cock with a passion.

"Oh god, I'm going to cum again." Bree responded to all this talk.

"That's it you naughty little slut, show my cock how much you love it!"

With that Bree's body started shaking and groaning loudly, with her eyes tightly shut as she leaned down to my chest letting her orgasm take her.

"That's so fucking hot, fuck me harder Phil, I need to cum too."

Phil began to pound up and into Trish with ferocity, it didn't take long before Trish herself was climaxing as well. I then spun Bree over to her back, but then stood up off the bed looking down at this hot young thing as she lay there with her legs open, that pretty waxed pussy looking up at me. So, I knelt down at the edge of the bed and pulled her body towards me so I could taste that sweet young pussy of hers. Phil had other ideas and turned Trish around so that they were in a 69 position.

After bringing Bree to another orgasm with my tongue, I raised up and pushed my cock inside of her, slowly at first then with harder deeper strokes. I learnt down to her face and kissed her, she gives very sensuous kisses, very passionate. As I started to pound her with all of me now, I could feel her next orgasm begin to stir. I kept up my pace and forced her over the edge, still kissing her deeply as she climaxed.

Phil had been fucking Trish in doggie, but we both swapped again so that Phil could fuck his date once more. I rolled Trish over onto her back up the bed, then lay on top kissing her deeply.

"I am enjoying tonight way more than I expected, this is so much fun." Trish whispered to me in between kisses.

"I'm glad you're enjoying it, I know I am."

I slowly started to slide my cock inside of Trish, I wanted to fuck her slowly this time, to savor it a little. She wrapped her arms around my neck, her legs around my back, pulling me in so she could kiss me deeper. I could hear Bree lying beside us moaning wish short sharp breaths as Phil had mounted her.

I focused all of my attention back on Trish, right now I wanted to enjoy the connection we were feeling as I slowly fucked her deeply, our mouths entwined in each other's.

We fucked like this for twenty minutes, just holding each other tight, kissing passionately. When I finally climaxed right after Trish, we held our embrace and continued our long sensual kiss. Finally, I rolled off her, looking over at Phil and Bree. Phil had already gone to the bathroom, Bree was laying on her side facing us, watching closely with a huge smile on her face.

"Wow! That was so fucking hot watching you two. You're in love with each other right? No way people fuck like that if they are not in love." Bree exclaimed.

Normally I would have said no, it's not like that. But actually it kind of was, I was falling in love with Trish so I didn't answer. I just gave Bree a smile and then looked into Trish's eyes before leaning in for another kiss.

After we had cleaned up, we made our way back to the lounge room, but Phil wanted to keep the night going.