If you haven't read "The Adventure Vacation" maybe take the chance and do it now. Same characters but who knows the shenanigans they will get into. The sex will come, but it won't be fast. If you want quick action, this won't be for you.
Chapter 1
I heard the ringback tone in my ear three times before I heard her soft but cheery voice pickup "Hello? Bobby?" my Mom cheerfully answered her phone, clearly seeing it was my number on the screen first.
"Hey Mom!" I replied. "Packing up to head home and just wanted to check in." I told her.
"Cant wait to see you babe. Hurry home but drive safely." she cautioned.
"See you soon. Love ya." I said.
"Love you too..." she trailed off as we both hung up.
I looked around my dorm room, empty with just a backpack left for me to grab and I would head out. So much had happened since we went to the inclusive resort, and returned home. When we arrived home from our flight 4 years ago Mom had sucked my dick in the car on the way home. We planned to keep the lines of communication open but that was the last time we fooled around. It just sort of didn't work at home like it did. I still jerked off thinking about her body, the way her mouth felt on my cock, her pussy's taste and smell and all the fun we had that week, it just didn't happen again. We talked about it several times but it is what it is. I think she felt guilty doing that in our home. Add to the fact that I found some motivation and decided to go to college. I just finished up my 3rd year and was looking forward to spending the summer at Mom's, regardless of what we might or might not do sex wise. I grabbed my bag, checked for last minute items and headed down to my car. Hugs and goodbyes to friends that were still packing up were had and soon I was on the 2 hour drive home. I set some music on and just drive, enjoying being done with school for a few months.
I pulled into the driveway soon enough and parked next to her car. I grabbed the few bags I had and when I turned to head up to the front door was met by...
"So good to see you!" she said, with a smile that would light up the neighborhood at midnight. She had on her standard, yoga pants and a sports bra. It seemed like all she wore these days- but I didn't mind. Her 38DD's were proudly displayed and her shapely ass looked amazing in the yoga pants. Her hair was the same as it was during our epic week a few years ago- brown and shoulder length. She looked like a mom, but like a hot mom. Like a hot mom I had fucked and sucked a few years earlier.
"Hi Mom. Good to see you too." I said and did the half hug thing as she took one of my bags.
"Is this all of it?" she asked.
"Yep. Small room so I don't have much at school." I told her as we walked up the path to house, chatting about traffic and regular stuff.
"Head to your room, drop your stuff and lets have dinner! Take you out to Jimbo's Burger, just like old times?" she said with her trademark smile.
"Sure thing." I hollered as I headed to my room. I opened the door and saw an envelope on the bed with my name scribbled in my mom's handwriting. Setting my things down I opened the envelope and saw it was a few sheets of printed paper but it was a cruise! Mom had booked a cruise to... the Bahamas!? Looking further it was a 5 night cruise with three stops in the Bahamas on a major cruise line. One stateroom, with two twin beds it said, and had both our names on it. It leaves tomorrow!? Grabbing the papers I skipped to the living room where she was sitting on the couch, waiting, trying to hold back a smile.
"Whats that?" she asked innocently.
"Like you dont know... Is this for real? Tomorrow?" I replied with multiple trains of thought.
"Yea! I wanted to surprise you. Feel like vacationing with your old Mom again?" she said, without any hint of what we did together last time. Images of her pussy flashed in my mind, her face as she lowered to engulf my cock, watching her fuck the friend we made named Ray...
"Well consider me surprised!" I finally snapped to and replied. "Im so excited." I said.
"Good, and are you ready for dinner?" she asked as she got up and tossed a light, crop top style shirt over her bra. We headed out to her car and chatted on the way to our favorite little greasy burger place called Jimbo's and went inside to order. Our food came and our conversation continued while we ate. About halfway through our dinner, Mom looked right at me asked if we could talk seriously about the trip.
"Sure Mom. Whats up?" I told her, giving her my full attention.
"Well, after our last trip, the resort, we said we would keep open communications about the...uniqueness of our relationship." she started, seemingly unsure what to say. I stayed quiet and listened. "I had fun then, and dont regret it at all. I just dont think we should plan for 'that' to happen again." she breathed a sigh and looked at me to gauge my reaction.
"I noticed the twin beds in the reservation, and I dont regret it either, and I agree with you." I spewed all my thoughts out at once, which was met by a smile from her.
"Ok. I mean, it was fun but certainly unconventional." she said with a laugh.
"To say the least Mom." I said, secretly unsure how I felt. I wouldn't want to force her at all or guilt her into sex but I would participate if she wanted to. At any rate she did such a nice thing by booking the cruise and I am sure we will have a blast no matter.
"Well, I'm glad we agree. Thank you for understanding." she said.
My mind suddenly went back to that resort hotel room sitting in the corner with Mom's damp panties in my hand watching her with Ray...
"Earth to Bobby..." Mom said, waving her hand around.
"Oh sorry. Just day dreaming." I told her.
She smirked and asked "Anything interesting? And feel free to tell me the truth."
"Uhm I guess, just thinking about our last trip a little bit." I admitted, feeling my face go flush.
"Oh yea? What part?" she asked, with a wide grin.
"A few different parts, a little about you and Ray, to be honest...." I trailed off, embarrassed to have admitted that to her. Not sure why, she watched me eat her cream pie after fucking him in front of me- so I dont know why this was so over the top for me.
"Oh that was a fun evening!" she exclaimed with a big smile.
"Have you stayed in touch by chance with him?" I asked, really unsure what the answer would be. I knew they exchanged numbers but its been so long now.
"Uhm, yea we have," she said quickly and without any details.
"You talk a lot? Or see each other?" I quizzed her.