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, 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."
