[MFM] My Year as a Sugar Baby Pt.3: The Trip

Part 1:

My Year as a Sugar Baby Pt. 1: The Massage [MF] from gonewildstories

Part 2: https://www.reddit.com/r/gonewildstories/comments/yvjt9e/my_year_as_a_sugar_baby_pt_2_the_party_mff

A couple pics from the trip:

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Edit: Sexual adventures start after the †††††s below.

“Cancun?!? Oh my God Damon I’m so excited!”

I jumped up and down, shouting into the phone, expressing my elation to my Sugar Daddy; who had just informed me of an all-inclusive trip we were taking together to Cancun. Complete with first class flight and a five star hotel.

We were about 8 months into our relationship and things had been relatively low key. Nothing as wild as my night with Carlos and Angelica at Damon’s house.

I would meet up with Damon a couple times a month for a date. We’d go shopping, have dinner, and then go back to his place for a massage and oral sex like our first time. In all our sessions together he’d still never fucked me, and only received head once because I insisted.

He explained that getting me off, got him off. That knowing he had the control over my body to make me cum over and over was enough of a power trip for him to keep him satisfied.

I referred to him as “Daddy” and he would call me “Pumpkin”, “Sweetie”, or “Baby doll”. When we were in public he’d insist I dress slutty and would take me to fancy places to show me off; the public thinking no doubt I was just his bratty step-daughter.

The day of our flight I met Damon at the airport and we went through the motions to get to our seats. I slept most of the flight after my first drink while Damon finished up some work.

After checking into our room, I couldn’t believe how beautiful the view was and peered off our private balcony in disbelief that Damon had provided this for me. I kissed him and expressed my gratitude by stripping naked and sitting on his face so he could be smothered by my ass, something I did on special occasions.

The next day at the beach, Damon insisted I take my top off at the clothing optional section. I have big DDD tits, with light brown areolas, and was happy to give them some sun and show off the goods.

After taking a dip in the clear ocean water, I asked Damon if he wanted a drink and headed up to the snack bar to retrieve them for us. I wrapped a towel around myself, but then decided against it, blew Damon a kiss, and headed to the bar, tits exposed and ass swinging, glistening in the heat.

That’s when I met Kevin and Jason, or Kev and Jay as they liked to be called. They were brothers traveling together for a friend’s bachelor party. My nipples hardened as I talked to these handsome brothers with my tits exposed. I wished their friend happy nuptials and they offered to buy me a drink. I declined, letting them know I was there with someone.

With impeccable timing, Damon walked up to order some food from the bar. Kev and Jay introduced themselves.

“We were just telling your daughter about our friends upcoming wedding!” Kev said, slurring a bit from the alcohol, staring at my boobs.

Damon bought the boys a round of shots and wished them a good rest of the trip as we walked away.

“Why didn’t you correct them when they called me your daughter?” I asked?

“I don’t know, kind of hot they think you’re my little girl” he joked as he playfully tickled me.

“You’re so bad Daddy” I laughed as we continued about our day.

We both got pretty drunk that 2nd day and decided to keep the party going through the night and to sleep in the next day before going on a snorkeling trip we had booked. Tonight, we’d dance.

The resort had its own club and Damon was a great salsa dancer. Something that equally surprised me and turned me on about him.

We arrived at the club which happened to be 3 floors. 80s/90s hits on level 1, Latin/world music on level 2, and hip hop/modern music on level 3.

We danced on the Latin music floor for quite some time, continuing to drink and laugh. I asked Damon if he wanted to check out the 3rd floor and he said he’d love to watch me dance but wasn’t interested in that music himself.

Damon headed upstairs to get a headstart on ordering our next round while I took a bathroom break. As I made my way upstairs I happened to run into Jay, from the bar earlier. He commented on how amazing I looked and asked who I was there with. I was going to explain about Damon until I remembered what he said earlier about me being his daughter.

In my drunken state I decided to have some fun and said, “I wanted to go dancing, but Daddy insisted on coming to make sure I’m safe. He’s waiting upstairs”.

Jay was there with his same group from earlier that day, and asked if it’d be ok with my Dad if we danced. I accepted his offer and we went upstairs.

Damon had our drinks ready and was surprised to see I’d found a dance partner so fast. He recalled meeting Jay earlier and bought him a drink.

“Daddy, is it ok if Jay and I dance?” I asked Damon.

“Of course baby doll, I’ll be here” he answered, smiling back approvingly that I was playing his game.

Jay and I had a great time dancing. I was grinding against his crotch and he ran his hands over my curves, squeezing my ass every now and then. We were pretty deep on the dance floor but I could make Damon out from where we were, watching us intently.

“Is your Dad always so protective?’ Jay asked.

“He can be. But he’s actually pretty cool once he gets to know you” I responded.

“I wish I could invite you back to my room but I’m sharing it with my brother” Jay said.

“Well… Maybe we can sneak back to mine” I whispered into Jay’s ear, producing a hotel room key from my bra.

I told Jay to make his way to my room and that I’d meet him there in 10 minutes after using the bathroom and talking to my Daddy.

Once Jay was out of sight I approached Damon and told him about Jay. He encouraged me to go have fun, and I said “maybe we can have some fun with this too, you and I?

He looked back at me with a questioning look.
“Maybe Daddy can catch his baby being a bad girl?” I cooed seductively. “Meet me in the room in 20 minutes”.

††††††††††††††††††††††

I walked away and hurried to Damon and I’s room. Jay was waiting at the end of the hall and I waved him over. We started making out as I slid the key into the mechanism, allowing us in.

Jay and I continued to kiss on the bed as we fumbled with each other’s clothes. Once his cock was out I started to suck him slowly, humming and moaning with my mouth full of Jay’s hardness. I sucked off the head with a loud pop and started licking Jay’s balls.

When he couldn’t take anymore, I got on my hands and knees so he could fuck me from behind. He grabbed my pony tail, hard, as he entered me roughly. He grabbed fistfuls of my ass and pressed them together as he pounded me, kneading the soft flesh as he thrusted with all his strength.

The room was filled with the sound of our bodies clapping together, Jay’s grunting “yeah, take it, yeah”, and my own screams of pleasure. I threw my ass back at Jay’s cock and we found a rythem where we were literally banging our bodies together as hard as possible.

In the midst of our power fucking, Damon had let himself in per my request, right on time.

Jay, startled, jumped off the bed, his young cock bouncing, still hard.

I screamed “oh Daddy!!”, Trying my best to sound shocked and embarrassed.

“It’s ok Pumpkin” he said softly. He looked at Jay and said “relax young man, my daughter is an adult and free to do as she pleases”.

Jay went back and forth looking at Damon and then myself, as if trying to solve an invisible puzzle.

“Now get back to fucking my daughter, not nice to keep a lady waiting”. Damon commanded.

Jay still looked like he was trying to plan the best escape but I hopped off the bed and got on my knees in front of him. I sucked his softening cock into my mouth and felt it twitch.

Damon took a seat in the hotel chair, his and Jay’s eyes never leaving each other’s stare.

I reached around to Jay’s ass, grabbed it tight and pulled him into my mouth further. Gagging slightly, I continued to deep throat his cock in front of Damon.

Jay closed his eyes and groaned in delight, undoubtedly not believing the scenario he found himself in.

He pulled me off from his cock, turning my head to face Damon. He told me to get on the floor and crawl over to Daddy.

I did as I was told and presented myself face down and ass up to Jay, with my head at Damon’s feet. Jay entered me roughly again and took no time in pounding me hard, his balls slapping hard against my pussy with each stroke. He pulled my hair back again and grabbed my throat tight as he fucked me. I looked at Damon who was staring back at me getting fucked by a young man we’d just met less than 24hrs ago.

“Your daughter’s a fucking slut man, you should feel how wet she is” Jay bragged, looking challengingly at Damon.

With that Damon leaned forward and pushed Jay back, his dick slipping out of me momentarily. I felt Damon’s fingers explore my well fucked pussy. He removed his fingers from my soaking wet honeypot and licked his fingers clean.

He looked Jay in his shocked face “you’re right, feels pretty wet” Damon mused back, “but maybe you should try her ass.”

Jay could not believe what he was hearing “What?!? You want me to fuck your daughter in the ass?” He asked, exasperated.

“Oh Daddy, I’ve never done that” I lied, “what if it hurts” I whimpered coyly.

The idea he may be taking my anal virginity emboldened Jay. Damon threw him a bottle of lube he grabbed from his own suitcase and I felt myself getting wet and more turned on knowing what was about to happen. I felt the lube on my asshole as Jay slipped a finger in to warm me up.

“Take it out. Show me you like this” I asked Damon, “Show me Daddy is proud”.

Damon stood up and let his shorts drop to his ankles. His cock was hard and already dripping a good amount of precum, confirming he was enjoying the show.

I stood up, encouraged, and lead Jay to the couch. He sat down, his own erection sticking straight out proudly. Straddling Jay’s lap, I rubbed some lube on his cock and eased the head of his dick into my tight ass. He groaned as the head popped past my anal ring and I slowly sat my ass on him until he was inside me to the hilt. I took a moment to breathe and began to slowly buck my hips forward, feeling him deep in my tummy as he violated my guts.

I rode Jay and he slapped my ass as he resumed talking shit to Damon.

“I can feel your daughters ass gripping my cock. You raised a real whore, Damon.” Jay said.

Damon continued to watch silently, his cock twitching in approval every time Jay spoke to him.

“She’s a real cock sucker too” Jay continued.

I leaned in and whispered something in Jay’s ear in between my grunts. Jay had a firm hold of my ass and was thrusting up into me as I bottomed out on his cock.

Jay looked at me and said “seriously?” before turning to Damon to say “get on your knees and crawl over here to my feet Damon”.

Damon did as he was asked and came over to get a good view of my ass getting pounded.

I turned around to face Damon and sat back down on Jay’s ass, riding him reverse cowgirl. Jay drew me to his chest, my back resting on him while I grinded with his cock deep in me.

“Make her cum” Jay commanded Damon.

Jay pulled my knees up, holding my legs open so Damon could get access to my pussy while my ass was still stuffed.

Damon began to lick me and my pussy started to spasm, making my ass do the same, gripping and releasing inadvertently on Jay’s dick. As Damon increased speed with his tongue and I got closer to orgasm, Jay was enjoying just staying buried in me, letting my anal muscles do all the work as they milked his cock.

I felt Damon’s fingers enter my sopping wet pussy and work their magic against my gspot. Jay could also feel him through the thin membrane separating my pussy and my ass.

He groaned as I felt his cock swell, nearing his own orgasm. Damon started really hammering against my gspot with his fingers and I started to cum, my pussy walls baring down on Damon’s fingers as my ass spasmed hard. All that screaming and squeezing was too much for Jay who started spurting rope after rope of cum into my ass.

As Jay and I were both cumming, Damon stood up and shoved his cock into my pussy. Jay was shocked because he thought my own Dad was fucking me, I was shocked because this was the first time Damon had ever penetrated my vagina. I moaned uncontrollably as Jay’s cock softened in my ass, plopping out, leaking his own cum onto his balls.

Jay held my legs back tight as Damon fucked me. I kept screaming “Yes Daddy, I’ve wanted this for so long. Oh goddd”

Damon kept panting “Baby, oh baby fuck it’s so good, baby, oh fuck”.

My sugar daddy removed his cock and took my hand, leading me to the bed. I got on all fours expecting him to continue fucking my cunt. Instead he spit on my used asshole and shoved his dick into me, slipping easily into my well fucked, cum filled ass.

Jay made his way over and put his already recovering, semi hard, dick in front of my face. Damon pulled my head back using my hair and I opened my mouth to receive Jay’s offering. Damon pounded my butt, causing my head to knock forward, forcing Jay’s cock into my throat further.

Without being asked, Jay slid underneath me in the 69 position. He began licking my clit and tongue fucking my pussy as Damon continued to fuck me even harder. I was screaming “Oh my God Daddy fuck me pleeease.”

Damon slapped my ass and told me I was a ‘good girl’, something he knew drove me crazy.

I came for a second time on Jay’s tongue. Damon instructed me to ride Jay, so I hopped on the younger guys cock and fucked him for all he was worth, bucking my hips back and forth on his stiff manhood. Damon went to his suitcase and pulled out the largest butt plug I’d ever seen. My eyes widened in interest as he started lubing it up, approaching me.

Damon instructed Jay and I to remain still. I kissed Jay deeply while I used my kegel muscles to keep his dick erect in me, squeezing him as tight as possible. I felt the butt plug begin to enter my ass and I moaned, struggling to take it in. Damon instructed me to breathe and to push out with my ass. I took another couple inches, engulfing the widest part before the rest popped in, stuck inside me.

All I could do was grunt like an animal as both my holes were stuffed to the limit. Jay began fucking me again with slow strokes, no doubt also struggling to accommodate his cock in my pussy with the plug in my ass taking up so much room. I could barely move, being so over stimulated, that Jay took control and fucked me from beneath. He announced his approaching orgasm and this time I hopped off to receive his cum in my mouth, something I rarely do.

I drank him and swallowed every drop. My ass was still plugged and I looked back at Damon and begged him to fuck me, to cum inside me.

He said “sure baby”, turning me on my back, missionary position, and started fucking my pussy. I felt so wet and loose I wasn’t sure if he was enjoying it but when he told me I was the best he’d ever had, I was happy.

Damon picked up speed, kissed me, our tongues feverishly wrestling. We both were groaning, panting, incoherent as we pushed into each other, our momentum producing a loud clap as our bodies thundered together.

“Baby, I’m going to cum” Damon groaned.

I had been waiting for that moment for almost a year. I pushed the head board with my hands so I could press Damon’s cock as far inside me as it would go.

Damon moaned as he started to release his load in me. He must have been really turned on because he’d never cum as much as he did then, his cum splashing out of me as he continued to pump.

We held each other tight, catching our breath as Jay layed next to us, starry eyed at what he just saw.

“That was the craziest shit I’ve ever experienced” Jay laughed.

Damon looked at Jay and smiled “well thank you for showing my baby such a good time young man. It was a pleasure.” Always the gentleman.

Jay left for the evening but stopped by every morning for the next couple days of his trip to fuck me, per Damon’s invitation. They didn’t double team me again but Damon enjoyed sloppy seconds a few times.

This was the only vacation Damon and I took together and we ended up breaking our arrangement a few months later when I met my now husband. There were no hard feelings and he was happy that I found someone that made me happy.

Source: reddit.com/r/gonewildstories/comments/yyluce/mfm_my_year_as_a_sugar_baby_pt3_the_trip