Ski Trip with [M]y College Ex [F] and Her Friend [F]

Skip to the ****** for the good stuff!

Background:

Several years ago, I (Tim) rented a cabin in Colorado with some friends from work to do some snowboarding and skiing. In total the group was planned to be: Mike and Janet (a couple that met at work), my good friend Ron, Ron's brother Steve, Paul, Carl and Amy.

Amy is a former co-worker but still in the friend group. In the week or so leading up to the trip, I had been so busy with work that I had been ignoring some of the group chat messages concerning the trip as I was focused on getting work done at my job so I could actually enjoy the trip.

Mike, Janet, Ron, Steve, Carl, and I had the same flight out, so we all got to the airport around the same time to catch our flight out. I learned a couple of things while we were waiting to board for our flight. First was that Paul wasn't able to come due to some issues that came up at home and second, Amy was bringing her friend Liz.

"Liz? You mean Liz (lastname) from college?" I asked Carl. Carl nodded and said that Amy became good friends with Liz after she left the company and moved to the same city.

Liz had been my long-term college girlfriend and while we left on good terms, I wasn't sure how I felt about her joining the trip in Paul's place.

When our plane landed, we picked up our bags and Ron and Steve led the way to the rental car counter. Mike mentioned that Amy and Liz should have landed around the same time and that we should keep an eye out for them.

As I was staring off into space while Ron and Steve waited in line to get the car keys, we were greeted by a couple of friendly "Hi's!" from behind. I turned around and felt like I took a step into the past. Amy smiled at me and said, "Hey you!" While Liz gave me a hug and said, "Hey Tim! It's been a while...you look really good, you lost so much weight." I told her she looked great too and she giggled a bit.

As we stood there getting caught up, I learned that Amy is enjoying her new job. But misses hanging out with the group and really enjoys Amy's company since she moved. Liz and I started making small talk and I basically learned that she was still the same awesome person I knew back in college. When Ron and Steve came back with the keys to the rental cars, we began walking to the car lot.

As we walked, we passed several couples. Amy commented that there were a lot of couples here and this prompted Janet to ask Amy if she was seeing anyone. She said unfortunately no as she had been spending a lot of time taking care of her mother and didn't have a lot of time for anyone.

I turned to Liz and asked if she was seeing anyone. She looked me up and down, bit her lip and mentioned that she had been very busy with her new career since we broke up, but recently she made partner at her firm and the work life balance was has been much better.

Upon hearing this, my heart fluttered a little and I told her I haven't dated anyone in over year and a half. She smiled and said, "Damn, so we've both had quite a dry spell! She then continued after sticking her tongue out a bit and said, "But hey, we're on a ski trip...maybe that will change." We both chuckled as I felt my dick lengthen in my pants.

For reference:

Liz is about 5'5" with dark brown, glassy eyes, and curly dark reddish-brown hair. She has an athletic build with with a small B-cup up top, skinny waist, and toned legs (lots of running. She also has a nice, round, full ass that that looks great even in baggy sweatpants.

We dated for one year in high school and three years in college before her career took her away. In those four years we've gotten to know each other very well and know what the other likes. In general we both had a very healthy sexual appetite when we were together.

Amy is around 7 years older than Liz and a little taller at 5'9", with green eyes, and lighter brown hair tied up in a bun most of the time. She is more fit than average (does lots of yoga) with nice skin (hard to explain). Her hips and ass are a little straighter and less full than Liz's, but she looks great in yoga pants which she typically wears. She also does massage therapy as a profession, so her hands are quite strong (I think you know where I'm going with this).

But, by far, her best quality are her big D-cups up top that easily fill out any shirt. Add in her thick frame glasses she wears and you get that naughty secretary look. In all my years of working and hanging out with her, I had gathered that she was pretty tame when it cane to being sexually adventurous (though you'd never think that looking at her).

For me (Tim), I used to be heavier in college but lost a lot of weight and actually got in pretty good shape. I am around 6' tall, and have short blonde hair with a fairly average face. I'm a but of a nerd, but my redeeming quality is that I've been told by several (including Liz), that I have a really nice dick.
We hit the road and headed to the cabin with our two cars. In my car was Ron and Carl up front and Amy, Liz, and I in the back with me in the middle. (In case you're wondering how I got the middle, we put most of the ski gear in the bigger car and Ron and Carl are taller than me so they got the front; I chose the middle so my knees weren't jammed up against the seats.)

The cabin was around an hour and a half from the airport, but the last 15 minutes or so was a bumpy snow covered road. While everyone in the car including me was talking about the view of the snow covered mountains, I couldn't help but catching quick glances of the girl's boobs bouncing from the road everytime I turned my head. Coupled with this and the vibration from the bumps, I was rocking a semi for the last bit of the journey. When we pulled up to the cabin, Liz caught me staring at her chest and give me a smirk.

She then looked at my dick that had grown down my pantleg. She raised her eyebrows at me, reached over, and discretley shifted it off of my leg and down a bit to make it less obvious. Apparently, it wasn't discrete enough, because when I looked to the other side to get out of the car, Amy was standing there in the threshold with her mouth open having observed the whole situation.

She mouthed the words quietly "You guys!" as we got out to walk up the the cabin. I smiled at Amy and and she smiled and shook her head in disbelief. As I walked off my semi I couldn't help thinking about fucking Liz again.

After the group ate dinner, we played a board game, had a few drinks and then everyone but me went to bed on the lower level. I went down to the main upstairs area of the cabin just below the loft and started playing with my new go pro camera and that I had bought for the trip. (I'm a bit of a nerd when it comes to electronics) I set it up on the shelf and pointed it up at the loft to see if it could get it to focus far away.

I sat back down on the couch and started playing with the app's feature that would show the camera feed on my phone. My nerdiness was interrupted by a friendly "Hey". I looked up and it was Liz standing there with pajama bottoms and a t-shirt that exposed the outline of her nipples.

She came over and sat down on the couch next to me and I showed her the view from the camera on my phone. She listened to me nerd out for a while before leaning in closer to get a better view, pressing her breast against my chest. Down below my pajama bottoms I felt my member start to thicken.

As we're playing in the camera app, she takes her eyes off the screen and looks in my eyes as I look back in hers. I make my move and lean in to gently kiss her. At this point, my dick is growing further and further down my pant leg. We made out for about a minute grabbing her tits as I kissed her(God did I miss them!).

I took her shirt off exposing her tiny pink nipples. I grabbed he boobs and started nibbing on her nipples. Lost in her chest, I managed to say between nibble, "I know your girls like the attention." She shuddered as the exhaled a small laugh. I pulled away for a moment to expose the tent I'm pitching in my pants.

Liz took one look and said, "Oh man I think he needs some attention too." With that, she reached down and unbuttoned my fly, freeing my dick. With her hand firmly around my base, my dick lengthened further in her hand.

"Jesus....," she said trying to find more words as she looked up and down my dick. "...Did you get even bigger since we were in college?!" I replied well, "Well I lost a good bit of weight since school, so maybe it just looks bigger". She stared at me in disbelief for a moment, let go of me, stood up, and walked across out of the room tovthe kitchen topless.

I watched lustfully as her firm ass cheeks flexed back and forth with each step. Moments later, after rummaging through the junk drawer, she came back with a tape measure and said, "Only one way to settle this!"

She placed her hand firmly around my base once more, gave me a few slow pumps base to tip, and extended the tape measure to check her claim. "Just under 7 inches, that's about a half inch bigger from what I remeber." I replied, "Do you also remember that he swells up more when you suck on him?" Her eyes narrowed a bit and her mouth opened slightly. She smiled with a sultry look. I stood up and she knelt down on a blanket.

She grabbed my dick and started dragging her lips back and forth across the head of my dick. Then she switched to the side and contined to go slowly back and forth went back and forth along the side of my for a few minutes, sll while maintaining eye contact with me. After a while, I began playing with her hair and lightly thrusting into her mouth. I increased my speed gradually until I was basically face fucking her.

My breathing intensified I thrusted harder and harder into her mouth. I dodnt want to cum too soon so stopped for a minute to catch my breath. She pulled out the tape measure again, "A little over 7 inches" she said with a little excitement in her voice. "Keep going, I can do better," I replied. She looked at me and said, "Have a seat...Let me see what I can do."

I sat back down as she put both of her hands end to end on my dick. The hand at the base squeezed first. The other hand stacked above it squeezed second, forcing more blood into my head making it rock hard. She then sucked vey hard on the tip and two to three inches of my shaft that protruded above her hands. The feeling that this gave me was unworldly and my heart started to race again.

(Truthfully, I've only ever even came close to replicating this feeling with a Fleshlight turned up to max suction, but that's a whole other story).

The feeling was INTENSE! I could feel the tension building, but couldn't must the words to tell her to slow down. Eventually, ai abruptly pulled out and said, "Ss-sorry, I didnt want to cum too soon, that was really intense." She smiled and said, "You look like you need a second."

I collapsed on the couch and she sat next to me. She grabbed her phone and noticed a few messages from the group chat....Apparently Mike, the leader of our group was awake in bed and sending us final details for the ski plan tomorrow (time, place for pass pickup, etc.)

After setting down her phone back down, she looked over at my phone that was still displaying the camera feed. Her eyebrows slightly raised and she smirked. Leaning in close, she whispered in my ear, "Amy is watching us from up in the loft...looks like she's enjoying the show!"

My breath shortened and I somehow, I got even more aroused than I already was. I had completely forgotten she was up in the small loft bedroom. Liz smiled and began stroking me again, watching Amy on the phone. After a few seconds, she spun the phone around snd showed me feed... there was Amy...MASTURBATING! I whispered back into Liz's ear, "OMG, that's so hot. I cant believe this! Liz leaned in and said, "I want to keep going." With that Liz resumed stroking me and while lightly rubbed her pussy underneath her bottoms.

As Liz stroked me faster and deeper she leaned into my ear and whispered, "I can feel you getting bigger. Come on baby!...Get nice and hard for Amy and I!" "ArrrgghUhhuuUuuhhhUhh," was all I could get out. Liz got down on her knees again and resumed with her "fleshlight sucking" skill, I felt the last little bit of blood I had left in my body engorge my tip. After about a minutes of this, I started gasping for breath with each drag of her lips. I almost couldnt take it anymore!

She released her grip and said, "You're not cumming yet!..but lets get the final answer on how big you are." Her smile grew as she extended tape measure. "Jesus." Was her only word before saying, "7.5 inches....and you're definitely thicker."

With a smile, she looked at me and said, "Do you know what I want you to do with this dick?" "Ummm", I stammered still gasping for breath. "No, nevermind." she said playfully as she took my cock back in her mouth and started bobbing up and down on me going deeper into her mouth each time until she starts bottoming out at my base. "When..did you..When did you learn to deepthroat?!" I asked out of breath. "We've all learned new things since high school..." she leans in to whisper, "and I think we've both learned we like being watched!"

I glance over at the video feed and Amy has her hand down her bottoms rubbing her pussy and her large tits heaving up and down, exposing one of her chocolate nips past the edge of her unbuttoned shirt with each breath...all while she watched Liz deepthroat me. As I watched Amy on the screen, Liz leaned in again and whispered, "And you thought they looked good bouncing in the car...this must blow your mind."

My mind was indeed blown for sure... I looked back at Liz's eyes once more while she slowed her speed. She took my dick out of her mouth staryed stroking me again. She looked me dead in the eye and said, "You know what I really want you to do to me?," At this point I could feel the pressure starting to build as precum started leaking out of my tip. "It's soo bad...". She said as she leaned in and began tonguing my frenulun quickly while stroking to the point that I began to feel both light-headed and out of breath. "Wha...Wha...what do you want me to do to you?" I gasped. "She replied, I'll tell you in a bit..first I want to show you something else I learned."

She took just me in her mouth about halfway in her mouth and sucked unbelievably hard while fluttering her tongue back and forth very quickly making my dick start to swell up with cum. She stopped and said, "Mmm, I love how hard you get when you're about to cum...are you sure you want to know?" "Wwhaa..what?" I barely managed to get out as my brain started to melt from the impending nut to end all nuts.

She sucked and fluttered me for probably another minute (though it seemed like an hour) as I gasped for breath trying to stave off my orgasm. Finally, she popped my dick out of her mouth, holding it lightly in her hand. She smiled with that sultry look again and said seven words that are still burned into the back of my mind today:

"I want you to fill me up"

I...COULD NOT...hold it any longer. I let out a long moan and my cock spasmsed so hard I nearly passed out. The first rope shot over her, barely grazing her hair, this caused her to recoil a bit, lining her up for the second rope which hit her square in the face. "Jerk!" she said laughing as she smacked my leg while I continued to cum. The next ropes hit in order: tits, tits, neck, chin, stomach. "Jesus", she said again, "I don't think you've ever cum this much!"

I sat there with my dick pulsing up and down while Liz licked the residual cum off of my tip. Above us in the loft, we heard a stifled moan that reminded us we had an audience. Both at once, we looked up at the loft to see Amy with one hand cupped over her mouth, the other hand cupped over her large exposed breast and eyes locked dead on us with her face beat red. "Sssorry!," she stammered as she cried a bit from from the embarrassment before running away.

Liz and I snickered for a bit and then she pointed at me, laughed and said, "Jesus, I wanted you to fill me up, not cover me! Lemme see some of those Kleenexs...better yet, just give me the box.

While I was helping her clean up the ropes of cum I threw all over her, both of our phones buzzed with a text message. It was from...you guessed it, Amy. "OMG, I am so sorry I was watching you guys, can you forgive me???? Before I could even contemplate a response, Liz quickly texted, "It's okay. We thought it was really hot." I glared at Liz and said, "What are you doing?!" Liz simply replied, "Just wait...I have a feeling." I nodded with apprehension and grabbed some of her Kleenexs to wipe off my dick better.

Our phones buzzed again: "Oh?" Amy replied. "I'm glad you're okay with it and I'm sorry I just...." "Just what?" I replied with a smiley emoji. Amy typed back after a minute, "I just.. couldn't help myself." Liz looked up at me and said as I had earlier, "oh man, This might be a REALLY fun trip."

We heard a few of the others begin to stir on the bottom level and figured it was probably time to call it a night before someone else caught us. On that note, we got ready for bed, retired to our separate rooms downstairs, and fell asleep.

The next morning, I got up early before the rest of the group and started the coffee. I sat down and unfolded a trail map to check out the runs on the mountain when in wandered Liz. We said hey to each other, looked each other up and down and smiled. "Haven't had a night like that in a while," she said. We both laughed and she joined me at the table.

Shortly after, Amy wandered into the kitchen rubbing her eyes. She stopped walking abruptly upon seeing Liz and I. She stood there with a deer in headlights look about her broke saying, "Oh...hey." she said turning beat red in the face. Liz confidently said "Hey yourself." And followed up with, "We knew you were watching us the whole time." "Huh?" Amy said surprisingly. Liz continued, "Tim had his go pro set up before I came in the room and.. Yeah, we were both pretty turned on." "Oh Yeah?...Tim, do I....turn you on?" Amy inquired. Liz then stuck her toungue out a bit before blurting out, "Tim's dick grew an extra half inch after I showed him the feed of you masturbating to us."

My eyes were then drawn to Amy's tight fitting athletic shirt under her button down top barely concealed her D-cups which were made more obvious as her nipples began to harden. Amy's jaw had dropped for a second before she regained her composure, crossed her arms over her nipples. Getting into the vibe of the situation she asked Liz, "I saw you measuring him...well, how big is he?"

My dick, shielded from view, grew down my pantleg under the table, easily to the 7.5" Liz had measured last night.

Not having consumed enough coffee (and thinking with my dick and not my head), I replied, "It's only the second day, maybe you'll have a chance to get a better look at it". Amy' breath shuddered slightly, grabbing the top of her shirt as her breasts started to heave up and down again from her breathing. "OMG, I cant believe we're talking about this!" She exclaimed.

This moment of horniness was interrupted when Mike came in and asked, "Can't believe we're talking about what?" Liz jumped in and said, "Cant believe we're thinking of going to the highest point of the mountain for the first run." Amy crossed her arms to cover up her protruding nipples again.

Ron came in as well and asked how everyone slept. Amy replied, "I slept fine, but..it was uh... a little hot last night." Liz and I smirked at each other, knowing it would be a fun trip! Liz got up to go get ready and I stayed at the table until the blood flowed out of my member. Eventually, I deflated and I got up to get ready for the first ski day.