Cruising With Stepmom

This summer's family vacation was a weeklong Caribbean cruise. My family consists of my father, my stepmother, my brother and me. My stepmom, Jen, is really the cruise enthusiast. Everything was going as expected until about a week before the cruise. My father is a supervisor at an engineering firm. My brother just graduated college and started working at the same firm. They had been working on a bid for some project for a while. Well as the date to leave for the cruise approached, the agency that was having the work done, changed the scope of work. This caused quite a stir and forced my dad and brother to have to miss the cruise.

Jen was really excited about the trip so she was so disappointed at the prospect of having to cancel. My dad told her that the vacation should go forward with just me and her going. We were able to cancel the airline tickets and the room my brother and I were going to share. My stepmom and I would share a room. Not a big deal, I would just get a cot and she would have the bed.

So for the descriptions of us. I'm 20 and about to be a college junior. I'm on the thinner side, preferring my workouts as running rather than weights. Stepmom Jen is 42. She's your typical mom/stepmom. Dark hair, brown eyes and carries a bit extra weight since she first married my dad. I wouldn't say she is fat. She's not. She's got the typical mom-bod; curvy. I've never viewed her as a MILF or SMILF. She's just Jen. One thing that I have noticed is that she has large breasts, probably about 38D or 38DD. She typically hides them with her style of dress, but on occasion I have seen them in swimsuits or tighter shirts.

My brother and I get along with Jen so I was not weirded out by just her and I going on the cruise. I know I wouldn't get to hang out with my brother and would be spending more time with Jen than I had planned, but no big deal.

So we fly down to Puerto Rico the day before the cruise and spend the night at a hotel by the seaport. One room, two beds. Nothing remarkable.

The next day we board the ship and go to our room. Problem. So instead of calling to make sure about the cot, we assumed it would be like a hotel and they could bring one in. They can't. Safety regulations and all that. So stepmom and I have to share a bed. A bit awkward, but we decide it's big wide enough to be ok and we will put a pillow between us.

We arrived at our first island overnight and went to the beach as an excursion in the morning. I was pleasantly surprised to see quite a number of women topless. Ok, I was surprised to see quite a number of women topless. I was pleasantly surprised to see a few of them. There were a few girls in their 20's that looked great. There were also a number of woman that I won't have minded if they kept their shirts on.

Anyway, so I spent some time admiring the surroundings while pretending to read my book. There was a very pretty blond girl about a year older than me that was the girl I admired most. She had an athletic body; nice toned legs, flat stomach and perky, uncovered boobs.

Jen was in the water in her pretty conservative one piece. After a while she convinces me to snorkel. It was cool seeing the brightly colored fish.

It had been about a year since I was with a girl. It had also been some time since I relieved myself with the hotel and small cabin not giving me the privacy needed. So the rest of the day was spent between in the water and checking out the boobs. After a while of checking out boobs, things started to stir in my pants, and I would go into the water to calm down.

Time comes to leave and there is a lot of people waiting for the shuttle. Seeing the number, I start to get worried about making it back before the ship leaves. So, as many people as can pack on the shuttle. To make extra room the driver wants us to sit on laps. I know, not entirely safe, but it's normal here I guess.

Jen tells me to sit on her lap.

I said, "no, that would be embarrassing", but told her she can sit on mine.

I have my swimsuit on with a t-shirt. She's wearing a wraparound around her waist and a t-shirt. The cute girl that I was admiring earlier sits next to us. She's now wearing her bikini top, but still looks great.

Between the sun, all the boobs, the cute girl, the recent lack of release, and pressure on my lap from Jen, my dick starts to stir. Oh no. I tried thinking of garbage, and anything else to prevent getting a hard on. It's not working. My dick was at a 90 degree angle, laying against my leg. As it's getting harder, it's getting a bit uncomfortable. I'm hoping Jen doesn't notice it.

Jen then says, "look at those pretty flowers and points out the window."

I look. I see the cute girl looks too. Then Jen lifts up slightly, grabs my dick and repositions it. I'm shocked. I guess she did notice.

She said, "Isn't that better?"

I think I mumbled, "I guess." I don't know why she did that.

So the roads in the Caribbean are rough and this one is no different. We're bouncing and rocking back and forth. This isn't helping my situation. I'm really trying to think of anything to help calm me down. I'm doing math problems in my head. I'm thinking of my chemistry class. Anything. I'm trying to think of how much longer we have to go. Well at least I can check out the cute girl's tits bouncing next to me. OH NO!! I feel the tingle in my balls. It's unstoppable. I feel the cum rushing from my balls though my dick. Jen is still inadvertently rocking on me. I instinctively grab her hip with my right hand and squeeze. I cum a lot. Like, I see stars, a lot. Jen freezes. I instantly go from euphoria to overwhelming dread. I'm embarrassed and scared. Jen's going to kill me. Plus I grabbed her in an un-stepmotherly way when I came.

Finally we get to the ship. People start getting off the shuttle. Cute girl leaves. Jen moves over and sits in the other seat. She pulled a towel out of the backpack and told me to wrap it around myself. She didn't seem mad.

We get back to the room and she tells me to shower and leave my trunks in the bathroom, she'll clean them. So I shower and then she showers.

After she's done, she says we should talk.

I was hoping to just move past this and never speak of it again, but I agreed.

I said I was sorry and start to explain.

She stopped me. She said feeling my hard on made her feel desired. She said she was surprised when she felt me cum, but after the shock, she felt sexy that she was responsible for making a man cum. She said she hadn't really felt sexy for some time and it made her feel good to be looked at as sexy.

I felt bad for her. While she's not really sexy, she's not unsexy. I couldn't tell her all the boobs I saw today and the cute girl had more to do with my cum than her. I just let her think it was her.

She then said, "I was surprised you had some much cum in your trunks just by having an old woman sitting in your lap."

I told her she was not old. I didn't really know what else to say so I said, "I guess sexy women sitting on my lap have that effect on me."

Then with a glint in her eye, she said, "Come on stud, it's time for dinner." Not sure, but I think she stressed the word "Come".

That's all for now.