Cruising with Stepmom Pt. 04

My stepmom, Jen, and I were on a cruise together after my father and brother had to cancel at the last minute for work. Jen is a curvy 42 year old. She has dark hair, brown eyes and large breasts. I am Brad, a 20 year old, fairly skinny guy.

Our physical relationship progressed from her accidentally making me cum while sitting on my lap to eventually having sex. The initial awkwardness of the situation has turned into desire for each other.

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After dinner, Jen wanted to go see a show. We were dressed up and she said it would be like a date. When we got to the theater, she wanted to sit in the back, so I complied.

Fifteen minutes into the show she leaned over and I felt her warm breath on my ear, "I'm still not wearing any underwear." I knew I was going to be in for another fun night.

I looked at her with her "I've got a secret" smile on her face. I moved my gaze down and could make out her erect nipples. I put my hand on her smooth left leg and slowly slid it up. I could just brush her strip of pubic hair, but because of the angle I could not do much. I continued to rub her leg and inner thigh.

Jen then began to rub my growing erection through my pants. Every so often she would slide her other hand up to her tit and play with it over her shirt.

She again leaned over to me and breathlessly whispered, "I'm so horny, I want to pull your dick out and suck on it."

I nervously said, "No, you can't do that here. People will see if your head is bobbing up and down on my lap."

She said, "Well scaredy pants, if you are going to make me sit here turned on, I'm going to have to get you as turned on as I am." She then continued to play with my hard on with her left hand, and then slid her right hand up her dress.

My assumption that she was fingering herself was confirmed when she took her hand out from under her dress and put a finger in my mouth. I could taste her sweetness. Her plan to turn me on was working and she knew it.

She continued to rub me. Finally, I leaned over to her and said, "You've already made me cum in my pants once this trip. You need to stop or it will happen again."

Jen then said, "Pull it out and cum in my mouth instead of your pants."

It seemed like a good idea. I was considering it, but there were people around and we would get caught. Then I started thinking, "Does a cruise ship have a brig? What will they do if they catch us?"

I snapped out of it and said, "That's it, you're being bad. We're going back to the cabin and you are going to be punished."

Jen's eyes got big and she said, "Oh, I am bad and I do need to be punished."

We left the theater and almost ran back to the room. Once back in the room, I sat on a chair and said, "Come over here and lean over my lap. It's punishment time."

Jen did as she was told. I lifted her dress and saw her shapely naked ass. I took a second to admire it. I gave her three firm smacks on her ass. Her ass jiggled and she squirmed. I gave her three more as her ass began to turn red. My hardon was pressing into her.

I said, "Mommy has been a bad mommy." Three more smacks. "Getting her boy turned on in public." Three more smacks. Rubbing her red ass, I said, "Fingering herself in public." Three more smacks.

"It's time for you to suck my dick.", I said. I knew it was either that or I cum in my pants.

As Jen got off me, I pulled my pants down and sat back on the chair.

Jen kneeled before me and took my hard cock into her mouth. She began to furiously bob her head up and down on my dick. The blowjob was full of urgency. It was like she wanted to see how fast she could make me cum. She was going to get her answer shortly.

Without warning, I exploded in her mouth. It surprised her a little, but being a pro she did not spill a drop. We then moved to the bed and finished getting naked.

We kissed. As I moved my kissing down to her tits, my finger easily slid into her wet and willing pussy. I slid another finger in her. After I worked my fingers in and out of her for a few minutes, I pulled them out and stuck them in her mouth. Jen sucked on them and ran her tongue around them like they were my cock. She knew what she was doing.

Jen told me that she wanted me to lick her pussy so I moved down and did just that. I would take a break from her pussy and kiss her inner thighs, then return to her sweetness.

I needed to fuck her again. I positioned my dick at the entrance of her pussy. Jen took hold of my hips and pulled me into her. We fucked missionary for a bit. I then rolled on to my back and told her to get on me.

Jen positioned herself above me. She took my cock and lined it up to her pussy. She lowered herself onto me and she began to ride me cowgirl style.

This instantly became my favorite position with her. Her big tits were begging for me to suck on them. I leaned up and put her nipple in my mouth. Jen was moaning. As I was leaning on my right hand, I moved my left hand around to her back. With my mouth still on her tit, I slid my left hand down her back to her ass cleavage. My middle finger rested in between her ass checks. I began to nibble on her nipples.

Jen's moaning increased. I moved my finger to underneath her and rubbed her pussy causing my middle finger to get slick. Jen's moans turned into grunts.

I put my middle finger on the rim of her asshole and applied pressure. The slickness of my finger allowed me to penetrate her ass to my second knuckle.

"Ugh. Oh yes, that feels good. Fuck me baby.", Jen said as she increased her hip action. I could tell she was bringing herself to a big orgasm.

Then, with my finger wiggling in her ass and my mouth on her tit, she said, "Oh god, I'm cumming." She pulled my face off her tit and stuck her tongue into my mouth for a passionate kiss.

Feeling her juices running out of her and onto me sent me over the edge and I shot my load into her pussy. Jen continued to ride me, slowing down until we were both spent and satisfied.

Jen laid down next to me and said, "You've made me feel sexy and desired this trip and I love you for it."

I told her, "I think this vacation just caused a part of you to reawaken. You've always been sexy. You've just repressed it."

We drifted off to sleep again naked.

We woke up and got ready for another beach day. Jen wore the dark blue thong bikini she got a couple days ago. It was a far cry from the conservative one piece swimsuits she packed for the trip. I liked how she became more adventurous on the trip.

We got to the beach and Jen wanted me to put suntan lotion on her.

I rubbed it on her back and legs. I felt weird about rubbing it onto her ass in public so I skipped it. She noticed and told me she really did not want to get a burn there, so I put more lotion on my hands and rubbed her ass in public. I did let my fingers rub under her thong, but only discreetly and quickly.

We spent the day on the beach and in the water. The beach was not a topless beach but I was able to admire a number of good looking women. Even though there were younger and skinny girls, Jen was the woman my eyes kept returning to. She looked great in a bikini. Her tits were a show stopper.

We returned to the ship and showered off the sweat and lotion from the day. When I finished my shower and got out of the bathroom, Jen was laying naked in bed. She said, "I'm ready."

Invitation accepted.

I walked over to the bed and kissed her. I kissed her down to her tits. Her body smelled of fresh soap. I continued kissing along her body. I kissed her stomach down to her legs. I kissed down her toes. I started sucking on her toes. I wasn't really into feet, but I spent some time worshipping Jen's. I licked the soles of both her feet. My kissing resumed up her other leg. When I got to her pussy, I began to lick and suck her pussy lips.

Jen was moaning. As I worked her pussy and clit with my mouth, I inserted a finger, then two fingers into her. I wanted to bring her to an orgasm to satisfy her because I knew what I wanted. As that was happening, Jen was licking and sucking on her nipple.

After some time of me enjoying Jen's pussy and Jen enjoying what I was doing to her, she reached her orgasm. While she was recovering from that, I moved up to suck on her tits. I reached for a bottle of lotion that was on the nightstand, and squirted some on Jen's tits, focusing on her cleavage.

Jen knew what I had in mind. She squeezed her tits together and said, "Fuck my tits baby."

I slid my dick between her glorious globes. Every few strokes I would thrust and hold my dick between her tits and she would lean down and lick me. I felt my orgasm building. I placed my hands over Jen's hands and helped hold her tits together. I started fucking those tits with abandon. Jen was encouraging me to cum. Finally, I withdrew from between her tits and grabbed my dick. I stroked it a couple of times and I came. I aimed the first couple of cum shots at Jen's tits, then I moved up and finished cumming in Jen's mouth. As I moved up, an errant shot hit Jen in the cheek. When I finished I revered Jen's curvy body. Her big tits had my cum on them. Her glowing face looked great with my cum on her cheek. I wanted this sight to last in my memory.

Jen broke my trance, "I knew you wanted to titty fuck me. Most guys do."

I smiled and said, "I couldn't help it. You're tits were made for sucking and fucking."

Later that night after dinner, we walked around the decks in the open air. Once a gust of air caught Jen's dress just right and lifted it. I could see her naked ass. I said, "I see you've really taken to going commando."

Jen said, "When I was younger and more confident in my body, I would go without underwear often. Once I got old and heavy, I became self-conscious and stopped. Knowing you appreciate my body and like me going without underwear rekindled my enjoyment of it."

"Jen, you are neither old, nor heavy. Just because you are not as skinny as you were when you were 25, doesn't mean you are fat. I think the extra pounds you may have put on look good on you."

"You don't think my ass looks too fat?"

"Nope, I like your ass. In fact, I have plans for it tonight."

"Oh really?", she said with her sexy smile.

Later that night, as soon as we walked into the cabin, Jen asked, "So what exactly are your plans for my ass tonight?"

I teasingly said, "I don't know if I should tell you or surprise you."

"This trip has been full of surprises." She walked over and kissed me.

I had gotten to know what gets Jen's motor running. I did the neck kissing, the nipple biting and of course the pussy eating. I brought her close to an orgasm, then positioned her doggie style. I moved behind her and began fucking her doggie. I grabbed her tit with my left hand as I continued fucking her. She was moaning and pinching her other nipple. She was urging me to fuck her hard. I again used her pussy juice to lube my finger. I slowly pushed it into her ass. She arched her back and pushed against me.

When I could tell that she was again getting close, I pulled both my finger and my dick out of her. My cock was slick with her juices and I put the head of my cock against her asshole. I wasn't sure if Jen was going to be okay with this and I hesitated. Jen sensed my hesitation and leaned back putting pressure on my cock. That was the signal I needed. With my left hand on her hip, I used my right hand to slowly guide my pussy slick cock into her inviting asshole.

The fit was tight. When my dick was halfway in, I started to pull out a bit, and then push in. I repeated this until Jen was able to adapt to my cock. I started fucking her with good pace.

Jen was grunting, "Fuck my ass." Then she said, "Fill my ass baby."

I was getting close. "Jen, I'm going to fill you with so much cum. Your ass is hot. You are so fucking hot."

Jen was playing with her pussy as I grabbed both her hips and with one final thrust, I unloaded deep into her ass. I swear, I think I saw stars.

After collapsing on the bed, Jen said, "It's been a while since I had anal. Thanks for reminding me that I like it."

With a smile I said, "That was my first time having anal. Thanks for letting me know I like it."

With a smile Jen said, "I hope you always remember your first time."

"Without a doubt, I will."

We awoke on the last day of the cruise. I was sad thinking that this was the last day that I got to have sex with Jen. I really enjoyed her sexuality.

This was a day at sea so after breakfast, I went to the gym. Jen said that she wanted to work on getting her body back into shape so she came too. I got on a treadmill and she got on a stationary bike. As I was running, Hannah and her sorority sister showed up to work out.

Hannah was looking like the athlete she was. She was wearing pink tight athletic shorts and a black sports bra. Her long blonde hair was in a ponytail. She got on the treadmill next to me. She said, "Hi", and started running. Her friend went to the elliptical.

She started to run at a faster pace than me. I looked to the side and admired her toned legs and her nice running stride. As I was doing this, I landed my right foot half on the tread and half on the treadmill deck causing me to stumble a bit. Hannah giggled.

After I ran for 45 minutes, I moved over an open section to stretch and do some pushup and core work. Jen joined me in the area and teased me, "I saw you almost wipe out checking her out."

I softly said, "I wasn't checking her out, I was looking at her stride."

Jen rolled her eyes and said, "Yeah, her stride."

I said to Jen, "Don't be jealous, I'm sleeping with you tonight."

We finished up in the gym and headed back to the cabin. We changed into our swimsuits and headed to the pool area in the later morning hours.

Jen was wearing her blue thong bikini with a wrap around her waist. I still couldn't get over how big her tits were. A few guys ogled at them as we passed. I felt proud that I was the one getting to play with them.

When we got to the pool area, Jen grabbed my hand and led my to a set of stairs. As she walked me up the stairs, I saw a sign that read, "Topless Sunbathing. Adults Only." When we got to the top of the stairs, I saw only one other couple there. They were an older, overweight couple. I didn't pay much attention to them.

We walked over to the opposite side of the deck from the other couple. We set up on our chairs. Jen removed her top, freeing her tits. She removed her wrap and lathered herself up with suntan lotion. Her rubbing lotion on her tits caused me to stiffen to half mast. She laid down on the lounge chair with her tits to the sun.

I stopped watching her and put on my own suntan lotion and laid down on my stomach. Jen saw this and knew that I didn't put any on my back. She got up and put lotion on my back. Even though I did my legs, she did them again. She seemed to focus on my upper thighs and then she slid a hand under my trunks and brushed my growing dick to tease me. She returned to her chair.

After a while I rolled over onto my back. Jen rolled over onto her stomach and asked me to put lotion on her back. I lathered her up, making sure I rubbed the side of her tits. I rubbed lotion onto her ass, spending a healthy amount of time rubbing it. I also rubbed lotion on her legs. Even, though I knew her legs had lotion, I figured turnabout was fair play. I rubbed her legs focusing on her upper thighs. She slightly opened her legs. I brushed her pussy as I was rubbing her legs. I wanted to slide her thong to the side and do more, but with the other couple here, I couldn't.

After I was done, I laid back down and opened my book. About 10 minutes later, Hannah and her friend came up the stairs. She smiled and waved to me. I returned the smile and wave to her. They set up and I returned to reading my book. I would occasionally glance over to Hannah. She was wearing a thong, laying on her back topless. Her smaller but perky tits were beautiful. Hannah's blonde sorority sister was also topless. She had bigger tits than Hannah's but they were not as perky. Hannah was clearly the hotter of the two.

I noticed movement from where Hannah was and looked over. Hannah was applying lotion to her friend's back. I could see Hannah's sexy back and sexy backside. Then Hannah laid down and her friend applied lotion to her back. As I was enjoying this sexy scene, I noticed that Hannah was smiling as she was looking at me. I was caught. I'm sure my face was more red from embarrassment than from the sun. I looked away. I saw Jen was now back to laying on her back.

Jen said softly, "She is pretty." There was no hint of jealousy in her voice. "You should go talk to her."

"I can't go up to a naked girl and just make small talk."

Jen said, "I need a drink, why don't you get me one and see if she wants one?"

I thought to myself, "My stepmom. My fuck buddy. Now my wingman? Or wingmom?" I looked at her cautiously.

She said, "I was jealous before, but now that I know you find me sexy, I'm not jealous anymore. Besides you're sleeping with me tonight. Now go."

I walked over to the two girls. "Hi Hannah and Hannah's friend. I'm going to get some drinks. Do either of you want a drink?"

Hannah's friend said her name was, McKenna. Hannah said they would like some iced teas. So I left to get the four drinks.

When I returned with the drinks, McKenna was still laying on her stomach, but Hannah was laying on her back, tits exposed. She knew I was coming back. She was showing off on purpose. I looked at her perky tits. She had small areola with cute pink erect nipples. As I reached over her to hand McKenna her drink, a drop of condensation dripped from the cup and landed on Hannah's toned abs. Hannah gasped when the cold drop hit her. I apologized,

With levity, Hannah said, "You did that on purpose."

I said, "No. If I wanted to do it on purpose I would do this." I took my finger and ran it along the cup to collect a bunch of condensation, and flicked it at her stomach.

Hannah gave a playful shriek. I handed her drink to her and returned to my chair.

I heard McKenna say softly to Hannah, "Yeah, he is cute."

I knew Jen didn't hear that, but when I got back to my chair and handed Jen her drink, she said, "She likes you."

I said, "Maybe." and rolled onto my stomach.

About a half hour later, Jen and I gather up our stuff and left. On our way to the stairs, I head Hannah said, "Bye Brad."

I said, "Bye Hannah. Bye McKenna."

On the stairs Jen said, "She definitely likes you, and I could tell you like her.", while looking at my crotch. My erection giving me away.

Once back in the room, Jen pulled my trunks down and started blowing me. I undid her bikini top and looked at her tits. I held her head in my hands and fucked her face. She was looking me in the eye as she was taking my whole cock in her mouth. Jen really knew how to suck cock and it was clear she enjoyed it.

I didn't give Jen any notice, I just held her with me fully in her mouth and exploded in her mouth.

After Jen licked me clean, she said, "Looks like someone was turned on."

Later that day, after dinner, Jen and I were at a club on the ship. We were drinking and doing some dancing. We were at the bar, when Jen noticed Hannah walk into the club alone. Jen waved to her.

Hannah saw and walked up to us.

Hannah said, "I was hoping to find you guys. McKenna is feeling seasick and didn't want to go out. I wanted to go out since this is the last night and I don't really know anybody else on the ship."

Jen was pleasant and said, "I'm sure there are tons of guys that would love to hang out with you, but I'm glad you want to hang with us."

Hannah said, "There aren't that many single guys on a cruise. Most guys are here with their girlfriends or wives. And besides, they are not as cute as Brad."