[MF] Sex Cruise pt 1 [long] [pegging]

This story takes place my senior year of college during our spring break. My FWB turned girlfriend, Jenny, and I were looking for a nice getaway during the break but didn’t want to be around our normal crowed. We had recently confessed our love for one another after nearly 3 years of fucking each other’s brains out. We decided a cruise would be a great time because no one would know us and we could be as wild as we want.

Now Jenny and I had (and still have) a very adventurous sexual relationship. We fucked in public, anal, mff, role playing. You name it we probably tried it at least once, within reason. So leading up to the cruise, I was pretty excited. She took care of all of the planning. We had a great balcony room and a sizable alcohol package. I was ready for a week long of fucking in a exotic places and seeing exotic places (and people).

So to describe Jenny I will say she is the perfect woman for me. Funny, charismatic, caring, strong, athletic and not to mention a dynamite body. She stands about 5’6″ tall and weighs about 145lbs. She is muscular thick in the way a sexy gymnast is. Great arms, muscular legs, bubble butt, toned stomach, decent C cups. She has a body built for sin and a mind to match. She has strawberry blond hair to her shoulders and a sexy half sleeve on her right arm. She played softball in college and was pretty damn good.

Anyways, the time finally comes for the trip. We make our way to the airport and board our plane. I can tell she’s excited because she can’t stop smiling. As we took our seats she whispered in my ear she has a surprise for me that night. I immediately get hard and she lightly rubs my cock over my pants.

Her surprises are always fun. She has given me strippers, other People to fuck, toys, you name it. Like I’ve said we’ve done almost everything.

We land in Miami and make our way to the boat. Boarding took forever and I was tired and pissed when we finally made it to our room. While walking to our room I made mental note of the amount of hot ass on the boat. I figured we might be able to rope in a third if the mood struck us. We went through the normal first day on the boat bullshit. After we started drinking at the bar. I decided to lay out near the pool and Jenny went back to the room.

Around dinner time I made my way back to the room and Jenny was getting ready. Standing at the mirror completely naked. I smacked her ass and rubbed my hardening cock on her. She pushed me away and said I had to wait.

We go to dinner. Got seated with a few nice couples (more on them later). After we ate we made our way to the club. Had a few more drinks and danced. Jenny flirted with guys and girls in front of me. She knew I’d be chomping at the bit when I saw this. She was very touchy with a Portuguese girl who looked a little like Olivia Munn. Finally after teasing me all day we head to the room.

I can’t keep my hands off her and I keep grabbing her ass and making out with her on the way back. In the elevator I press her against the wall and slide up her tight dress to find she has on a pair of crotchless panties. I nearly melt. I love seeing her in sexy lingerie. She’s soaking wet and I can’t wait to burry my throbbing 7.5″ cock in her.

We get in the room and she pushes me on the bed. She said she’d be right back and headed to the bathroom. I started getting naked and stroking in anticipation. She emerges from the bathroom a few minutes later and my jaw drops. Jenny has on the sexiest dominatrix outfit I have ever seen. Leather corset, leather boots, fishnets, and a realistic 7″ strap-on. She walks to the foot of the bed and says “you get to be the dom at home, but out here it’s all about what I want. And tonight I want that ass!” I nearly came right there. Jenny knows about my bisexual past and the time I had spent with the sexy cross dresser Tyler. I was normally a top but had been known to ride a mean cock.

Jenny then pulled me down to the edge of the bed and starts stroking her fake cock and my own. She tells me how this has always been a fantasy of hers to dominate me. The strap-on she’s wearing is made to give her pleasure while she fucks me. I’m still dumbstruck by her appearance and demands to fuck my ass. Just then she starts going down on me. Licking from my balls to the tip. Circling my glans and tugging on my foreskin. She then starts working more into her mouth. Soon she has my whole cock in her mouth and throat.

I’m loving every second of this sloppy wet blowjob. I start bucking my hips in ecstasy. Jenny pushes my hips down and pulls up my legs. She smacks my ass and says “I told you this was about ME!” With my legs still in the air, Jenny starts sucking my balls. She starts making her way to my smooth hole. (Side note: I’m almost completely smooth, Jenny’s preference.). Jenny grabs both my ass cheeks and spreads them as I feel her hot wet tongue plunge into my asshole. I’m in total bliss. I can’t believe what’s happening. Jenny is showing a new side of herself and I’m loving it. With her face pressed deep between my cheeks, I can feel her tongue reaching my levels inside me. I nearly came just from her rimjob.

Satisfied I was ready Jenny stood up and poured lube onto her fake cock. She told me to beg to get fucked. At this point I would have begged her for anything. “Please Jenny fuck my ass with your big cock.” She aims towards my glistening hole and pushes forward. There’s some resistance but not enough to cause a lot of pain. Through squinted eyes I can see the pleasure in her face. She’s loving this as much as I am. Jenny inches into me telling me how much of a hot slut I am. Finally she bottoms out. I’m rock hard as she starts fucking me slowly. Her pace is agonizing with pleasure. I beg her to fuck me harder. Jenny starts speeding up, lifting my legs onto her shoulders. The strap-on attachment inside her is working wonders. I can tell she’s getting close. Her pace quickens and I see her head lean back and she starts to shake. I attempt to start stroking my own cock when she stops me. She says she’s not done with my ass.

Jenny pulls out and lays on the bed next to me. She tells me to get on reverse cowgirl. I feel like such a slut. This is my favorite position to ride real cock. I straddle Jenny’s hips and start working myself down her fake cock. When I finally have it all inside, she’s smacks my ass. I love it. She keeps degrading me telling me what a slutty bottom cock whore I am. I keep bouncing on her cock using her words as encouragement. I then leaned forward and started almost twerking on the fake cock. This visual and the added stimulation must have been too much for Jenny. I can hear her start saying she’s about to come again. I double my efforts trying to bring on another orgasm.

Just then she tells me to turn around. I spun around keeping the dildo in my ass. I start riding her cock again as she grabs mine. As I’m riding the strap-on she’s stroking my cock. I’m so horny and about to burst. Jenny tells me to come for her. She starts to buck into me harder nearing her own orgasm. This is too much to take and I shoot cum all over her corset and tits. I can feel Jenny shaking underneath me and I know she’s cumming too.

I lean forward and kiss her as the fake cock slides out of my ass. Jenny breaks our kiss and looks me in the eyes and says “I don’t think you’re done. Clean up this mess.” I start licking the cum off of Jenny. It’s so hot being pushed around by the sexiest woman alive. After I’ve cleaned the cum, Jenny pushes me to her now strap-on free pussy. She’s glistening wet. I can’t help myself but dive in. It didn’t take a lot but I was able to make her cum again with my mouth. Satisfied for the night we cuddle up and fall asleep in each other’s arms.

Let me know what you think. There’s more stories from the cruise. Mostly kinky stuff. And as always PMs welcome.

Source: reddit.com/r/gonewildstories/comments/5sf8sq/mf_sex_cruise_pt_1_long_pegging