Almost a Threesome [MFF]

When I was 25 a friend of mine, Jordan, asked if I wanted go on vacation with him as he had never been to an all inclusive resort and he knew I went at least once a year. I was excited about it because the girl I was really into (Sarah, from my other stories) had ghosted me after going on a trip of her own and I was also going through some drama with an ex. We booked a place that had pretty good reviews but wasn’t too expensive, assuming there wouldn’t be a lot of young people if we went with something too luxurious.

The place was nicer than we thought it would be based on the price we paid but the crowd also seemed a bit older. I remember after walking to the room and dropping our bags off Jordie asking me “Do you think we’ll meet anyone that doesn’t have grey hair?”

I honestly didn’t care all that much, the drinks were free, the ocean was blue and the sand was white. Reading a book while lounging in a beach chair and listening to the waves I was oblivious to anything going on around me and that included the gorgeous woman walking down the beach topless.

“Dude… dude… dude… dude!” Jordie basically yelled. I looked in the direction he nodded in and saw her just in time as she moved from her knees to laying down flat on her stomach beside another woman who was laying flat with a book over the end of her lounger.

“Dibs.” He said laughing as he got up to go get us more drinks. Now, this might be a weird thing to say about a male friend but Jordie is good looking, charming, in fairly good shape and importantly never forgot a name. I honestly can’t think of a time when he failed to pick up a woman he said he was going to but that always made him fun to be around because he started a party wherever he went.

A little way down the beach I could see him coming back from the bar carrying four drinks, his face beaming. When he stopped at the two women I started imagining how the conversation was going, laughing to myself trying to think of terrible lines he would use while trying not to stare at her breasts. It didn’t surprise me at all though when the two of them picked up their beach bags and towels and followed him over to our chairs.

“Wake up nerd, this is Cassandra and Tammy.” He said as I shook their hands politely and quickly realized from their sexy accents that their first language was definitely french.

Cassandra was about 5’4 or 5’5 with pale skin and shiny black hair that ran down all the way to her small breasts. She was wearing a very classic looking floral bikini and I was immediately attracted to her.

Tammy was the woman that had been topless before Jordie had invited them over, a bit taller than Cassandra 5’6 or 5’7 with brownish red hair just past her shoulders. She was already well tanned with freckled skin wearing a pink thong bikini that her gorgeous tits looked ready to bust out of. At this point I honestly thought they were fake because they looked *too* perfect. You could also see her abs which once we knew her age amazed us both.

They almost immediately asked our ages and when I told them we were both 25, they giggled to each other in french and went a quiet.

“And yourselves?” I knew it wasn’t the smartest thing to ask but I don’t know how you avoid the question after you’ve just told someone your own age.

“I’m 43 and Tammy is 46.” Cassandra answered smiling. Her english was definitely better than Tammy’s.

“She lies, I’m 28.” Tammy explained looking at Cassandra pretending to be offended.

“You would have fooled us.” Jordie laughed smiling at her and looking her up and down, as smooth as ever.

Jordie and I moved chairs closer to the ones we already had and Cassandra took the one between the two of us while Tammy was on the end furthest away from me. Cassandra and I chatted about books and politics and realized right away that we had a lot of interests in common. The other two laughed and giggled and found reasons to playfully touch each other. Somewhere in all of this they told us that this was their second last full day and that they had a la carte reservations that we could join them at for dinner.

“Nick and I were going to do something romantic but I guess we’ll have a few days for that after you leave.” Jordie joked. I think for a few seconds Tammy actually thought we were gay because she seemed genuinely confused until Cassandra explained it to her in french and she laughed squeezing his shoulder.

That night after a fun dinner the four of us broke off into our obvious pairs and I could tell something was wrong after holding Cassandra’s hand while we walked down the beach. At this point I was just trying to give the other two time in whichever room they had decided to go back to.

“I have a boyfriend.” She blurted out like it had been bubbling up inside her. “I know I should have mentioned it before now, I just… we were having such a good time and then it felt like it was too late. I didn’t want to lead you on though.”

“You haven’t done anything wrong!” I chuckled as she looked at me nervously “I’m young but definitely capable of being just friends with a beautiful woman.” I could be smooth too.

“Thank you, you are really sweet.” She leaned in and kissed me on the cheek and I realized at that moment that I hadn’t really thought of her sexually. She seemed to me in some way unattainable, like she was too classy and well put together to have any interest in a young guy like me.

“What about Tammy?” I asked realizing they had purposefully not talked about relationship statuses.

“She’s going through a really terrible divorce, but please don’t mention it.” Her eyes were serious and I had no reason to pry.

“Understood, won’t say a word.”

We continued walking and she took my hand again, I could tell she was a bit conflicted and I understood. There was something about being so far from home in such a beautiful place that made you feel like you should be able to do anything you wanted. Eventually we had walked in a big circle around the resort and were back at her room. We agreed to meet for breakfast and she kissed me on the cheek again with a soft “Goodnight.”

When I got back to our room I opened the door slowly calling out that I was back in case anyone wasn’t dressed but Jordie was under the blankets on his bed completely passed out and alone.

The next day I went for breakfast with Cassandra while Jordie stayed in bed extremely hung over. I wasn’t sure if maybe Tammy had drank too much too but I was kind of happy when I saw Cassandra waiting for me outside the buffet alone. Being polite I knew I should ask about Tammy.

“She’s a bit embarrassed about last night and thought Jordie would be here. Where is he?” She asked, clearly having gotten details of last night that I hadn’t.

“Too hungover to get up, why what happened?” I asked her as a host showed us to a table.

After he had taken our drink order and walked away she told me how Tammy hadn’t been able to get Jordie hard and was convinced it had something to do with her age.

“That’s ridiculous, yesterday when we first saw her neither of us could stop staring. He just drank too much.” I reassured her putting my hand on hers.

Cassandra smiled at me “Good, I told her that’s what probably happened but shes going through a lot right now. Lets get something to eat!”

We spent the rest of the morning chatting over coffee about anything and everything except our lives back home eventually deciding to go get changed and meet up by the beach. Jordie still wasn’t feeling up to it so I met up with both gorgeous women in bikinis and we picked out our spot for their last day. Tammy was quiet at first but seemed a little happier when I apologized for making Jordie drink so much and promising that none of us were going to do shots that night.

Later in the afternoon we decided to move up to the pool because the beach got pretty windy. When we got there Jordie was finally out of bed and probably had been for a while as he was chatting with a group of really cute college girls. The one in the black thong bikini had an absolutely perfect ass and was practically hanging off of him while the two others watched and giggled along.

Tammy, Cassandra and I put our towels out on three of the pool chairs and I offered to go get drinks. As I was about to walk away Cassandra grabbed my wrist and pulled me in close to her and for a second I thought she was going to kiss me but she just whispered “Don’t make it a big deal.” I knew what she meant and nodded before heading to the bar.

“Hey! Alexis, Sam, Laura this is my buddy Nick!” Jordie introduced me to them and I chatted while I waited for mojitos to be made. They were all in their second year of university making them 19 or 20. I managed to give Jordie a look while they were giggling among themselves and he knew exactly what I was trying to say with my eyes.

“I know man, dick move, but look at her fucking ass.” He whispered to me as Alexis stood with her back to us. I have to admit that this girl did have one of the cutest asses I have EVER seen before or since.

“Jesus,” I mumbled quietly enough that only he could hear me “It’s all good, I’m sure she’ll understand, but I’m still going to use our reservation.” I reminded him we were supposed to go for dinner with Cassandra and Tammy.

“Shit, I totally forgot,” He looked at the girls “Hey girls, Nick is gonna ditch me for dinner can I go with you three?” They agreed and we said we’d all meet up that night to watch the show.

I had dinner with Cassandra and Tammy, both of them looking beautiful in light flowing sundresses. I never explained Jordie not being there and neither of them asked. I think at this point Tammy really was over it beyond feeling a little like the third wheel even if nothing could happen between Cassandra and I. She was wearing this small silver cross that drew attention to her cleavage and caught me looking at least a few times smiling and they would both laugh when I would look up at the sky or around the restaurant.

After dinner and the show we walked to the lobby bar and spotted Jordie with Alexis. They were standing at the bar and all over each other, sloppily making out. We went to sit down a little ways away and Tammy started talking to Cassandra in french. I sat there sipping my drink and watching the two of them have a conversation that seemed incredibly fast while also taking at least five minutes.

“Sorry Nick, Tammy wants to go back to the room.” Cassandra said finally turning back to me as Tammy went quiet.

“Oh okay, I totally understand.” I smiled at Tammy and I wanted to explain that Jordie wasn’t just an asshole he was probably too embarrassed to talk to her again but I knew with her limited english and my non existent french that conversation just wasn’t possible.

“Why don’t you see if you can get a bottle of wine from the bar and we’ll have it on our balcony?” Cassandra suggested and I eagerly agreed having thought because they were getting up early to leave she had meant that they were headed to bed.

I bribed a bartender who handed me a cheap but good size bottle of red wine and looked around realizing Jordie and Alexis had disappeared. I walked to Cassandra and Tammy’s room on the other side of the resort closer to the ocean and knocked on the door. When they didn’t answer I Just walked in guessing correctly that they were already out on the balcony and so couldn’t hear me. Walking through their room I noticed they had pushed their two beds together and it seemed odd to me. I put three disposable cups down on the desk and poured out some wine for each of us and then carried them onto the balcony.

“Hey handsome,” Cassandra said standing up from one of the plastic chairs and kissing me on the cheek while taking a cup from my hands “Did they give you a bottle?”

“Yeah but I had to fight them for it.”

“My hero!” She laughed before biting her lip.

Tammy stood against the balcony railing quietly watching us flirt and motioned that I could have the second chair to which I just waved my hand at her.

“You are the guest.” She said with her sexy accent insisting.

After our second or third glass of wine mine and Cassandra’s hands were touching again and Tammy said something in french. “She says we’re cute together.” Cassandra explained with what I thought for sure was the *I want to be kissed look* women get but when I leaned in she softly shook her head no while smiling. She sighed dramatically and stood up going inside the room taking our two empty cups with her. As soon as she was gone Tammy sat down on my lap sideways facing the door.

“You should kiss her,” She hissed playfully as she put her arm around me and rested her hand on the back of my neck “If you don’t kiss her she’ll regret it later.”

I knew exactly what she meant so when Cassandra came back out with our wine and gave us a look like she knew we were plotting something Tammy slid off my lap and I stood up. I walked towards her and standing directly in front of her leaned down and kissed her bottom lip. Her eyes closed, she kissed me back hard and I put my hands on her waist pulling her into my body. I pressed against her and I think Tammy took the wine out of her hands. When our kiss broke she exhaled hard and whimpered before turning around and going back into the room. Confused I looked back at Tammy who was beaming happily “That was pretty.” She said quietly before sliding the balcony door closed.

I took a cup of wine from her and sat back down in the plastic chair. Tammy, despite there now being a free seat sat down again on my lap and I knew with only the fabric of my light shorts and her brown sundress between us she could feel I was growing. She wrapped her arms around my neck and stared directly into my eyes and I fought as hard as I could not to peak at her cleavage which was amazing with her arms in the position they were in.

“There’s nothing about you that isn’t sexy…” I said breaking the silence feeling like she deserved that reassurance after what had happened. She looked like she might cry as she leaned in and put her lips to my ear.

“You can have anything.” She whispered before kissing my cheek. I had one hand on her back and the other resting on her flat stomach which I slid up her body and squeezed one of her big natural tits through her dress.

“You have amazing breasts.” I mumbled.

“You like my tits?” She asked, her accent making me chuckle.

“Very much.” I responded pushing my hips up a little so that she could feel how hard she was making me against her ass.

“Lets go inside.” Tammy said taking me by the hand and sliding the balcony door back open before I could ask if we should wait longer for Cassandra to fall asleep. When we got in the room Tammy put her finger up to her lips as if to say that we should be quiet and pulled me to the end of her bed. Cassandra had changed and was wearing a white tank top with her blanket pulled up just below her small tits. Her eyes were closed but she had been outside about 5 minutes before so there was no way she was asleep.

Tammy sat down on the end of her bed and put her long smooth legs on either side of me leaning over a bit to unzip my shorts. She pulled them down with my boxers. I didn’t even see my own cock before she put her mouth around the head and started sucking. I swallowed hard and put my hands on her shoulders as her tongue flicked at my frenulum making my shaft twitch. Her technique was so incredible I could feel my toes curling as I pulled the fabric on her dress off of both her shoulders exposing a strapless white bra. I unclasped it and she moved her arms to let it fall away exposing her big soft tits and tiny nipples, perfectly tanned.

“Fuck.” I whispered trying to get a good look at them past her quickly bobbing head taking her brownish red hair and putting it to one side of her neck. “Wait… wait Tammy.” I whispered, I honestly wasn’t used to such good oral and didn’t want to finish too early. She slowed down and looked up at me smiling.

“Bon?” She asked licking her lips, topless with her dress around her waist and still covering her lower half down to her thighs. I stepped out of my shorts and boxers which had still been around my ankles and pulled my v-neck t-shirt over my head. Her hands went immediately to my waist pulling me close to her as she traced my abs with her tongue.

I think it was at this point that I could tell Cassandra was watching us, her eyes open just a little and a slight smile on her face. I pulled on the bottom of Tammy’s dress as she sat on the bed and she stood up understanding I wanted it off of her. Her white panties matched the bra that was already on the floor and she pulled them down slowly, putting on a show for me. She exposed a thin landing strip and that her panties had been basically stuck to her pussy, they looked soaked as she pulled them all the way down. As soon as her panties hit the floor I was on my knees with my hands on her thighs pushing them apart as she sat back down on the edge of the bed. I tried to tease her by kissing and sucking the inside of her thigh but she grabbed me by my short brown hair and pulled my face into her pussy. Looking up at her I ran the length of my tongue along her slit, she was wetter than any woman I had ever been with and tasted amazing. She moaned loudly through clenched teeth as I licked her, the tip of my tongue touching her clit each time I lapped at her wetness. She put her soft tanned legs over my shoulders and started to buck her hips to the rhythm of my licks. This gorgeous woman was using my face to get off and I was loving every second of it. After only about five minutes and without warning she pulled my hair hard and I buried my tongue inside her as she grinded against my mouth, her whole body tensing hard as she came. Her head fell back flat on the bed and she was breathing hard smiling as she turned and looked at Cassandra who was for whatever reason still trying to pretend to be asleep.

I stood up, just as hard from being made to eat Tammy’s pussy as from the amazing blowjob she had started to give me. She shimmied up the low bed a little so that I could position myself over top of her and I did. I waited a few seconds with my hand around my shaft to see if she would suggest a condom and when all she did was look up at me biting her lip I parted her soaked pussy lips with the head. She closed her eyes and let out a long sigh as I easily slid deep inside of her. She put her small hands on my waist and started to rock her hips, meeting my slow thrusts. At some point I looked over at Cassandra and wasn’t surprised to see her eyes open watching as I fucked her friend who was 20 years older than me. Her blanket was still only pulled up to around her waist and I could tell through her tank top that her nipples were hard and that her hand was between her legs. She gave me a little smile and as obvious as it seems now I think this is when I first realized this was going exactly how the two of them had wanted it to. Wanting to put on a good show for her I put a hand under Tammy on her back and lifted her higher onto the bed so that we were even with Cassandra who was only about two feet away to my left. Once I was sure she had the best view possible I started to speed up, fucking Tammy deep as she wrapped her legs around my waist from below. As our bodies started to slap against each other Cassandra rubbed faster and I tried to make eye contact with each of them evenly, looking back and forth between them. Tammy’s face was flush and it turned me on to think that I was the first man fucking her since her husband even if that wasn’t the case.

I was getting close when Cassandra quietly said something in french to Tammy that she had to repeat once we had slowed down and were making less noise. “Get behind.” Tammy instructed looking up at me excitedly. I was glad for the break as I had been getting pretty close and didn’t want to disappoint either of them by finishing too quickly especially since Cassandra was now giving the instructions as to what she wanted to see. Looking down as I pulled out of Tammy’s perfectly groomed pussy I swear the head of my cock was dripping with her juices and I hoped it meant she was enjoying this at least half as much as I was. She rolled over and up onto all fours as I knelt behind her firm ass. Not a thing about this woman would make you think she was older than 30. Cassandra had stopped rubbing herself, waiting for us to start fucking again and Tammy playfully reached over to try and pull on her blanket. Cassandra smiled but shook her head no just as I pushed my rock hard cock back inside of Tammy’s dripping slit. She let out a loud moan, keeping her head turned towards Cassandra as I started to fuck.

“Good boy….” Tammy groaned in her thick accent as I started to take her hard from behind. Cassandra started to let out quiet little moans while she watched and it was driving me crazy that I could hear but not see how furiously she was rubbing her wet pussy. Her pale face had become flush and she was opening and closing her eyes as her hand moved quickly under the blanket. I put my hands on Tammy’s waist and started to fuck her even faster while trying not to bury myself too deep, I wanted so badly for Cassandra to cum watching us that she was now all I was focused on and lucky for me it didn’t take her much longer. She suddenly closed her mouth so tight that you couldn’t see her lips and stopped moving her hand. Even in the dark it was obvious she was shaking, her eyes fluttering as she stifled her moaning. I imagined her fingers pressed hard against her clit as she came watching me pound into her friend. It took Tammy pressing her ass roughly into my groan for me to realize I had completely stopped moving and just froze watching Cassandra cum.

“Sorry.” I laughed quietly as Tammy giggled and Cassandra smiled before turning over. I’ve never been sure if she was embarrassed, feeling guilty about having a boyfriend back home or maybe just wanted me to focus on Tammy but I like to think it was the latter. Tammy slid off my throbbing cock and turned around pushing me back so that I had to brace myself with my hands. She leaned down and made sure I was watching as she licked the length of my shaft from the balls to the head before starting to suck her juices off. Her gorgeous ass was high and I reached over her and squeezed it with both hands as she started to deep throat me without making a sound. I could feel my full balls against her chin as she wrapped her hands around me and squeezed my ass as if trying to pull me down her throat.

“Holy fuck!” I groaned as I started to explode without being about to warn her but she wasn’t surprised. She loudly gulped down stream after stream of my hot cum without sliding her lips more than an inch back on my shaft. I could feel myself shaking as she expertly drained me, taking my entire load directly into her throat and then looking up at me and licking her lips.

When I woke up I was laying flat on my back with Tammy laying on my chest still completely naked but Cassandra was gone. I was a little worried Cassandra had regretted her part in the night but at the same time it was all too amazing to feel bad about. Tammy woke up about five minutes after me and even though I wanted to go find Cassandra I couldn’t refuse when she wanted to suck me off again.

Later on Tammy and I found a happy Cassandra at the buffet having breakfast.

“You two looked to cute to wake up!” She told us clearly not upset as Tammy squeezed my arm.

I exchanged emails with Tammy and the three of us said goodbye about an hour later as they got on their bus to the airport.

Source: reddit.com/r/gonewildstories/comments/ecktct/almost_a_threesome_mff