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This is the third part to the Cruising with Stepmom series.
My stepmom, Jen, and I are 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.
Day one of the cruise while Jen was sitting on my lap, she made me cum. On day two, I caught her masturbating and we masturbated together.
As I laid in bed recuperating after that incredible experience, I began to think that I might have a chance at having sex with Jen. I realized in both experiences we’ve had, she did not intend for anything sexual to happen, but she did seem to enjoy it when it did. Again, as I was wrestling with this, I also realized that the only sexual touching of each other was when she put her toe on my balls. I had not felt her body. I was afraid, if I step across a boundary, it would not only ruin my relationship with Jen, but my relationship with my father as well.
I found out later, that at the exact moment I was having this internal struggle, Jen was in the bathroom cleaning up with other thoughts. She later told me that after she sampled my cum from her chest, she wanted more.
As soon as she entered the bathroom, she ran her fingers through more of my cum and sucked on them enjoying it. Then, as she was in the shower, she played with her pussy bringing her to another orgasm. It was at that moment that she realized that she wanted more, but was also worried about the same issues I was worried about.
I drifted off to sleep that night thinking about Jen. I was dreaming about those huge tits. I’m pretty sure I fell asleep with a boner. The next thing I remembered was thoughts of Jen’s mouth on my dick. It felt so good, so real. I started to realize that I was in that foggy area between sleep and consciousness. Even though my eyes were closed I began to notice that daylight was seeping into the room. I opened my eyes and saw Jen with my dick in her mouth, looking up at me.
She smiled and said, “I was hoping this would wake you. You overslept. We need to get moving.” She then stuck my dick back into her mouth and continued to suck me.
I lifted my butt off the bed and slid my shorts down to my knees. Jen was alternating between running her tongue around my head and deepthroating me. When she would look at me with those lustful dark brown eyes, I knew she was enjoying the blowjob as much as I was.
As I regained my awareness, I realized she was dressed, but I wanted to play with those tits I was dreaming about. I slid around to be able to reach her boobs and was disappointed that she was wearing a bra under her shirt. I think she realized what I wanted and put the blowjob on pause while she took off her shirt and bra.
She said, “I hope this makes you cum quicker. We need to get going.”
As she continued the blowjob, I was able to reach down and play with one of her tits. It felt so fleshy and was topped off with a pointy nipple. I squeezed her tit and pinched her nipple. I wanted to suck on her tit, but the angle was not right, so I contented myself with fondling her boob.
“Come on baby cum for me. I need you to cum.”
I felt the beginning sensation in my balls. They began to churn. I said to Jen, “I’m getting close.”
She said, “Yeah, baby. Come on. Give me that cum. You cum tastes so good.” She then took her hand and began to play with my balls as she was blowing me.
“Oh Jen, here it comes.”
“That’s it baby cum in my mouth.”
With my left hand, I pinched her nipple harder than I intended. My right hand went to the back of her head and held her onto my cock as I emptied my load into her eager mouth. She kept me in her until I was spent. She then licked me twice.
She got up and commanded, “Shower and get dressed quickly.”
As I was trying to catch my breath, I said, “You’re incredible. That was fantastic.”
“Get ready. We can talk later.”, she said as she was putting her bra on.
I said to her, “Why don’t go without a bra today? I think it would be sexy knowing you have nothing on under your shirt.”
I could see her thinking about it.
Finally, she said, “Why not?”, and put she sleeveless blouse on over her bare tits.
After I got ready and we had breakfast, we took the shuttle into town for shopping. It was the typical Caribbean tourist section of town with lots of shops selling trinkets and souvenirs. We went into several of the jewelry shops. Jen enjoys shopping so I was being the good stepson (or good boyfriend??) and going into the stores with her. She bought a pair of earrings with a matching bracelet at one store.
We went into a clothing store. Jen said she wanted another new bikini. She held up a blue one and asked what I thought about it.
Mischievously I said, “Why don’t you put it on so I can see how it looks on you?”
She said, “I’m not putting it on in the the middle of the store.”
I half-jokingly said, “Okay, casino siteleri come over here to the side of the store and put it on.” I was thinking of that beautiful chest, naked under her shirt.
She laughed and playfully hit me. I told her, “I think the dark blue would look great on you. You should get it.” She did.
I could tell this vacation changed Jen. I didn’t know it was a return to her younger self or if this was a new Jen. While Jen had always been pleasant, now she almost seemed like a giddy school girl. She was more adventurous than I had seen her.
In between shopping, I asked her what made her “wake me the way she did”. Even after what we’ve been through, I still didn’t feel right using the word “blowjob” with my stepmom.
She then told me about her masturbating in the shower the night before. She told me that she likes the taste of cum. With the previous night’s sampling of my cum, she made up her mind that she was going to give me a blowjob at some point. She took my oversleeping as her opportunity.
She then started to explain to me that her and my father, as with any couple, started off having sex constantly. As time progressed, it slowed to once a week or once every two weeks. Between my father being 6 years older than her and working a lot, he doesn’t seem to want to have sex as much.
She confided to me that since her and my father were married she put on some extra weight and felt that may be part of the reason my father didn’t want to have sex with her as much.
I could see the sparkle in her eye from earlier in the day left and was replaced by sadness. I told her, “You both are crazy. You are super sexy. Yeah, you have curves, but they are in all the right places. Your tits are mesmerizing. That ass in my lap is what started all this. My dad’s crazy for not jumping on you every chance he gets. I’m struggling not to reach under your shirt at this very minute.”
She smiled and said, “You are so sweet. You are going to make some girl very happy,” Her sparkle began to return to her eyes, and nipples became erect.
The rest of the afternoon consisted of some more shopping and some more flirting.
We got back to the ship later in the afternoon, leaving us not much time before dinner. Back in the cabin, Jen told me that going braless was a turn on. The fabric rubbing against her nipples was tantalizing. She said her nipples were hard the whole day.
I said, “I don’t believe you. Show me.”
She then slowly lifted the bottom of her shirt to the underside of her tits. She paused there, teasing me for a second, then pulled the shirt the rest of the way over her head.
Yup. She wasn’t lying. She had hard nipples. I moved to (maybe pounced upon?) her and started sucking her right nipple. I worked circles with my tongue. My left hand was on her bare back. My right hand went to her left nipple and started fondling that.
After a painfully short time, Jen said, “Alright Tiger, I have to get ready for dinner.” Then left me and my boner to go shower.
After dinner Jen said one of the bars was having a 90’s theme night and she wanted to go. I agreed to go with her since I had my fill of the casino, but I said I would only go on the condition that she again go braless. She readily agreed.
The bar was pretty crowded and fun. Jen was enjoying a number of tropical drinks. I had a couple of beers. Thank you international waters.
At 10:00, they brought out the karaoke machine so people can sing to 90’s music. After a few people sang, I convinced Jen to sing. She did a passable version of No Doubt’s Just a Girl.
While Jen was singing, the girl from the beach the first day entered the bar with another girl her age. After they found a table, the girl came up to the bar next to me. As I was watching Jen, the girl began to talk to me.
“Your mom’s pretty good.” she said.
I said, “Yeah, thanks. She’s not my mom though.” It was weird. I didn’t want to say she was my stepmom, because the way we act would probably raise eyebrows.
To change the subject, I said, “I’m Brad.” Slick, I know.
The pretty blond girl, told me her name was Hannah. Hannah had green eyes. I remembered her athletic body and perky tits from the beach. Her toned legs were on display in her tight black minidress.
She was here with one of her sorority sisters on a vacation. She played field hockey for a small college in the mid-west. She had a sweet southern accent.
As I was talking to Hannah, Jen came back. I introduced Hannah to Jen. Both Hannah and I said Jen was great.
After a few minutes of small talk between us, I could sense jealousy from Jen. It wasn’t blatant, but knowing her, I could feel it.
Jen then finished the rest of her drink and said, “Well, you kids have fun, I’m going back to the cabin.”
I did the math in my head. I could spend the time with this pretty girl and hope that I get to where Jen and I had gotten, or go back to the cabin with Jen. It really was canlı casino a no brainer. I told Hannah it was nice meeting her and I hoped to see her around but I was pretty tired. I was also going to back to the cabin for an early night.
Once back at the cabin, to my disappointment, I did not walk into Jen masturbating. She was getting ready for bed.
She said, “I thought you were having fun talking to blondie.”
In my mind, I patted myself on the back for picking up on Jen’s jealousy. I said, “I was having a good time with both you and Hannah. When you left, I decided that you were more fun.”
Jen seemed to lighten up a bit. She cautiously questioned, “Is that just because I gave you a blowjob?”
I said, “Not ‘just because’. But if I had to pick between spending time with her and spending time with you, I pick you.”
Jen was beaming now. She walked up to me and and kissed me. Our first real kiss. The kiss was full of passion. I kissed her back. I ran my hand up the side of her neck and through her hair, slightly gripping her hair. I tilted her head a bit and moved to kiss her neck. I gave her soft kisses up her neck until I reached her ear. There, I nibbled on her ear and breathlessly whisper, “Jen, you are so hot.”
My left hand reached around Jen, and slid up under the back of her shirt. I rubbed her smooth, naked back as I returned to kissing the side of her neck.
From there, I unbuttoned Jen’s shirt from the top down but left her wearing it. I worked my kisses down from her neck to her upper chest, then to her chest between her cleavage. I was tempted to go straight for her tits, but I wanted to make this something that Jen would remember.
With my left hand still rubbing Jen’s back, I kissed down her cleavage to her stomach.
Jen felt self-conscious about her stomach and said, “Don’t kiss my fat stomach.”
I just looked up at her and in between kisses I said, “I’m going to kiss you all over tonight. I think your stomach is sexy.” I then directed my kisses to her side and up her ribs. I continued kissing along her lower rib to just under her tit. Finally, the moment I had been waiting for, I gave Jen three kisses on the underside of her tit and reached her nipple. She was in as much anticipation as I was. I gave her nipple two kisses and then wrapped my mouth around her nipple and sucked. I heard her take a small gasp.
My left hand was still rubbing her back. My right hand went to her tit and held it as I continued to suck it. I looked up to Jen’s face to see that she had her eyes closed and was softly cooing.
At that point, I removed the shirt from Jen. Somewhat reluctantly, I detached my mouth from her nipple and kissed around her side to her back. As I turned her around, I had my hands on her hips and kissed, up her spine to her neck. I kissed down her spine to just above her pants. I retraced the path kissing her up to the nape of her neck.
My left hand grabbed a handful of her hair and tilted her head to the left. I then kissed the right side of her neck from behind. My hard on was pressing into her ass. I knew she felt it because she leaned back into me. My right hand moved around to her tit and I softly pinched her nipple. Again, I nibbled on her ear, and said, “Jen, I want you so bad.”
She stopped her cooing to say, “It’s nice to be wanted. You are making me feel so good.”
I walked her over to the bed and turned her around to face me. After another lustful kiss on the lips, I unbuttoned her shorts and slid them down. I was pleased to see a wet spot in the front of her panties. I kissed the wet spot then slowly pulled her panties off.
I took a moment to admire Jen, and told her, “I love your body.” I helped direct Jen into laying down. I started kissing her body again. This time going from her right hip, down her leg, up the inside of her leg. When I got to her right inner thigh, I worked my way around her pussy. Jen brought her hands to the sides of my head and tried to direct me to her pussy, but I resisted. I kissed her across her body above her pussy, going through her landing strip. Jen let out a whimper of frustration. I made my way to her left hip. I repeated kissing her left leg just as I had done on her right. As I got to her inner thigh, Jen forcefully directed me to her pussy.
She commanded, “I need you to lick me pussy.”
I said, “But I haven’t kissed the rest of your back.” Then I ran my tongue from the bottom of her pussy to the top. She was almost dripping. It tasted like the best dessert I could imagine.
She gasp and said, “Yesss. You can kiss the rest of me later. Eat me now.”
I worked my tongue along her sweet tasting lips. I pushed my tongue into her. I played with her clit. I continued to eat her out. I inserted my finger into her. When I looked up at her, she held her tit with her right hand and she began to suck on her own nipple. That was a sight to see. After a few minutes, Jen grabbed my head and held it against her pussy.
She nearly kaçak casino shouted, “That’s it. I’m close. Keep going, I’m going to cum soon.”
I doubled my efforts and sure enough, she tensed up and she came. I must admit. I felt like such a stud. I made my stepmom cum. The night before she came, but she was pleasuring herself. This time it was me.
Jen said, “Okay, now it’s your turn.”
I was still fully dressed, so I took off my clothes. Jen took my rock hard cock into her hand and lower her mouth onto me. The blowjob earlier that morning was rushed and I was not awake for the beginning. For this one, I was able to enjoy it from the very beginning. Jen was an expert at sucking dick. I was so turned on from making her cum, I knew I wouldn’t last long.
Jen sensed it too. She was bobbing her head up and down on me quickly. Her hand was riding up and down my cock in unison with her mouth. Then for the second time that day I said, “I’m getting close.” And for the second time that day, I came into my stepmom’s mouth.
I pulled her up to me and as I kissed her, I was rewarded with a salty kiss in return. I said to her, “I’m not done with you tonight.”
With desire in her eyes, she said, “I hope not.”
I worked my kisses down her chest. I took both her tits in my hands. I was able to squeeze them together and get both her nipples in my mouth at the same time. I gently worked both her nipples between my teeth. I continued to play with her tits, one or two nipples at a time until I felt my dick getting hard gain.
I laid my body on top of hers with my legs in between hers. I kissed her neck and lowered my dick down until it was touching her pubic hair. Simultaneously we moved until my dick slid into her soft, wet, womanhood.
Jen just said, “Fuck me Brad.”
I slowly started thrusting in and out of her. I was thankful that she blew me because I’d probably would have shot my load at that point. Because she did, I knew I had some ability to last. Some.
After a few minutes of missionary, I got on my knees while I was between her and lifted her legs onto my shoulders. This was a great position. As I pounded into her, I could watch those fantastic tits rock up and down. I would occasionally turn my head to either side and kiss her legs, down to her ankles. I continued kissing along her foot and finally sucking a toe into my mouth.
Jen was moaning and encouraging me with, “Oh yes.” and “This feels so good.”
After a while, I rolled her into doggie style. I was getting close at this point. I was slamming into her and every once in a while I would slap her ass.
Jen was grunting and begging me to fuck her harder.
I reached around to grab her big tit as I was fucking her. I told her to play with herself.
She then was leaning on her face with one hand squeezing her tit and the other hand rubbing her clit. She grunted, “Cum in me. I need to cum.”
So I grabbed both of her hips and fucked her as fast and as hard as I could. One last thrust in and I held her ass against me. I pushed my dick into her as far as I could and came.
Jen felt me cumming and that triggered her orgasm. I held her tight against me as we both rode our orgasms out. We collapsed onto the bed with my dick still in her. I kissed her sweaty neck.
As my deflating dick fell out of her, I rolled off of her and said, “This is the best vacation ever.”
She looked at me, smiled, and said, “I agree.”
We then showered and went to bed. We fell asleep naked holding each other.
The next morning we had “the talk”. I couldn’t tell anyone. If my father found out it would be terrible. What would people say if it got out? What happened on the trip could not happen at home. All the things I would expect to hear. I agreed with all her points though I was hoping it would continue to some extent at home.
We got ready for the day’s excursion. We were going on a tour of a rum distillery. As Jen got out of the shower, I handed her, her outfit for the day; a sundress.
When Jen asked where her panties and bra were, I told her she was going without them today.
She gave me a playful look and said, “You’re naughty. What has gotten into you.”
“You’re sexy and I think being naughty turns you on which turns me on.”
Jen put on the sundress with nothing underneath. The v neck drew your attention to her generous cleavage. The bottom of the dress stopped at just above her knees.
When we were on the shuttle for the tour, the dress rose to mid-thigh when Jen was seated. Fortunately the shuttle was not crowded. I was able to rub her leg a couple of times. Jen looked nervous, but did not stop me.
Throughout the day whenever we were last in line, I would put my hand on her ass and rub it a bit. One time we were talking up a set of stairs, I ran my hand up her leg and brushed her pussy.
She let out a little yelp causing a couple people to turn around to see if she was okay. Her face was a bit red. I didn’t know if it was embarrassment or excitement.
When she got a second to talk to me in private, she said, “You’ve got to stop. Being naked under this is enough of a turn on, if you touch me again, I might jump on you right in front of everyone.”
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