Grandmother And Winter Break

This is a follow-up to Grandmother and Summer Break. You might want to read it first. Hope you enjoy and if you have any comments please send me an email.

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Well after a few fun filled days with Grandmother reality set in and it was time to head home. My mother talked to Grandmother a few times over the summer and she kept going on about how much she enjoyed my visit with her and how I really took care of her small repairs and other needs. I knew what she referred to but mother was clueless for all the better. I did have a chance to visit with Grandmother a few times over the summer before heading back to college. Every visit was better as we really got very close in a lot of different ways emotionally and physically. We spent a lot of time having mind blowing sex but we also spent time to really get to know one another over dinners, long walks and sitting on the deck visiting. My Grandmother is a very interesting person with a vivid history as a well educated and well traveled older woman. She has an air about her but also a little mystique that I find charming. Her story telling and prior life is fascinating to say the least.

I got a call from my mother in November at school and she informed me that Grandmother wanted to take me on a cruise over the Christmas break as my Christmas gift. She wanted to clear it with mother before asking if it would be okay and if I might be interested in going. Later that evening Grandmother called regarding the trip.

She said, "David would you be interested in going to the Caribbean over Christmas break with me? We would have a nice stateroom with much privacy to satisfy our sexual cravings for each other and some time in the sun."

My response was, "Sure Grandmother as long as I have a chance to spread your legs apart and take you for my pleasure I'll be more than happy to be your Boy Toy!"

She laughed at my response and replied, "I think you know what toy I plan on playing with so keep away from those young college girls as I want you horny."

Grandmother didn't know but since we have been fucking, college girls are not as enticing plus I am always horny for her. She is one sexy lady and a fantastic sex partner with no limits. She taught me more last summer about sex than I could ever learn in a lifetime with college coeds. After visiting and talking about the trip for awhile she said to be checking the mail in the next few days for a package.

As promised a few days later a package arrived including a plane ticket, itinerary and a check for $2,000. Grandmother said the money was to update my wardrobe for the trip as she wanted me to be stylish. The next day I did some shopping for some new clothes to include some dress slacks, shirts and a new suit and sports coat. Darn near spent the entire $2,000 but that is what she wanted and I didn't want to disappoint her.

As the school year was winding down towards year end and the holiday break was fast approaching I was eagerly looking forward to the cruise and some time in the Caribbean with some warm weather and bright sunshine. Our fall was cool and rainy so a nice warm climate sounded really good and very inviting.

The plan was for me to fly to Miami and meet up with Grandmother at the Miami airport. Our flights were only an hour apart so it would work out very well. I was to meet her in baggage claim and we would get a shuttle or taxi to the cruise ship. Headed to the airport and left on time. Got into Miami on schedule and went to baggage claim to retrieve my bags and wait on Grandmother. Her plane was also on time and we connected as previously planned. She looked good as she sauntered into the baggage claim. She had on a skirt with a tight blouse that accentuated her breasts. I could see she had been to a tanning salon as she had a bronze tone to her skin. She saw me and gave me that wicked smile that sent me a message that our time would be extremely sensual, exciting and over the top. I got a stirring in my loins thinking about what was going to transpire over the next few days. She came up to me and took me in her arms for a deep, long kiss. She also grabbed my ass and squeezed it as I was hugging her. She directed me to the carousel to claim her bags and there were many to say the least. She signaled for a porter to help with the bags which include my two and her four. It looks as if she packed for an extended stay but that was just being a woman. We grabbed a cab and headed to the port to board the cruise ship. If you have ever been on a cruise you know it takes a while to board due to the increased security and the screening process. We finally got thru all the processes and headed on board and found our room. We decided to grab a bite to eat and explore the ship. It really takes awhile to get your bearings on a cruise ship due to the size and layout. We spent nearly all afternoon wandering around the ship and getting lost numerous times.

Grandmother reserved a balcony room with two twin beds that would be converted to a king size bed for our pleasure. The balcony was nice as we could spend time sitting out in the evenings enjoying the warm weather but also give us some privacy.

After touring the ship and getting our bearings we went back to the cabin to get ready for dinner. I put on my new dress slacks and a nice dress shirt while Grandmother wore a casual dinner dress and looked really nice. We headed to the dining room for dinner where we met our dinner companions a middle aged couple from Ohio. These people would be our dinner guests every night we ate in the dining room on the cruise. They seemed very pleasant and we enjoyed their company over dinner.

As we were dining Grandmother would place my hand in her lap and would pull up her dress more and more. I soon came to realize she had her legs spread without any panties and was encouraging me to stoke her bare, naked, freshly shaven pussy between dinner courses. By the sly smile on her face I could see she was enjoying my exploring as she would squeeze her legs together making it difficult for me to retrieve my fingers. She was going to be having a good time on this trip if our first evening was an inclination of what was to come. After dinner we went to the casino for some fun and after dinner cocktails. A few older gentlemen had their eye on grandmother but her interest level in them was negligent. She knew what was going to transpire later and an older man was not in her plans.

On the way to our room we stopped on the deck and could feel the warm evening breeze. The sun was setting in the distance and it was very sensuous and romantic. I stood behind grandmother as she was against the rail and put my arms around her waist as I slowly pressed my crotch against her ass. She pushed back and spread her legs as I slowly moved my hand and fingers around to the crack of her ass and played with her increasingly wet pussy. I could feel her juices flowing down her legs and heard moaning in my ear. She was becoming very excited so I thought we needed some privacy or our stay on this ship could be short lived.

In our cabin Grandmother went into the bathroom to get ready for bed. I was sitting on the bed when she came out and walked up to me in a long flowing silk robe.

As she opened the robe and exposed her large breasts with nipples taunt she said, "David you aren't going to believe this but I forgot to pack any pajamas so I guess I going to have to sleep naked the whole cruise."

She let out a deep laugh that quickly turned to a deep moan as I buried my face between her breasts. I slowly sucked on her nipples and they became so firm as I alternated between them. I slipped my hand up between her legs and she was already wet even more so than at dinner. She loved for me to slide my fingers in her ever so deep. She would squeeze her legs together to increase the friction.

"Oh my it feels so good and I have been wanting you since dinner. I can't believe how excited you make me and every time is better than the last," she gasped. I took off my clothes and she proceeded to push me back on the bed and straddled my legs. She took the head of my cock and rubbed it on her clit ever so slowly. Her eyes were glassed over as she kept rocking back and forth with my cock tight between her pussy lips. She finally rose up and impaled my seven inches to my balls in one stroke. She stopped to catch her breath and then slowly worked my cock in and out of her cunt slowly and with short strokes. She gradually picked up her speed with the depth of her strokes and I could hear and feel my balls slapping against her ass. As I took her nipple in my mouth she started a low moan as I knew she was coming.

I pulled her head to mine and said to her, "Come on Grandmother milk me, make me cum."

With that we both exploded as she impaled me again and tightened her grip on my cock. She collapsed on my chest and laid there till she caught her breath and then rolled over.

She looked at me and said, "Wow, what a start to our vacation. This could be the trip of a lifetime if we don't kill each other." With that she laughed and rolled over. I pulled her tight against my body as we fell asleep to the rocking of the ship.

The next morning started out slowly as we awoke intertwined in the bed. Grandmother was lying on her stomach with her soft, enticing ass in the air as I slowly ran my hands over her cheeks. Her skin was so smooth and soft and felt so good. She awoke with a smile as I slowly squeezed her luscious cheeks and played with the crack of her ass. I love how soft she feels when I stroke her and also how responsive she can become. We played around for awhile and decided to get up before it went any further as we wanted to save our lovemaking for later when we had more time. We also needed to get to breakfast as we had a shore excursion planned for later.

We spent the day in port sightseeing and shopping. The day was warm with tropical breezes but we certainly worked up sweat exploring the shops. We sampled some local foods during lunch and drank some local beers which were refreshing. We decided to head back to the ship and take in some sun by the pool prior to dinner. We went to our room and changed into our swimsuits and headed to the pool area for some much needed R & R. We found a couple of lounge chairs in the sun so we could work on our tans and enjoy some enticing tropical drinks. I had to be careful as smooth and tasty the drinks were they could also be somewhat potent. After a couple hours of sun we decided to go back to the room and get ready for dinner. One thing about cruising is you do have a tendency to eat quite frequently and the majority of the food is quite tasty.

Grandmother jumped in the shower first to freshen up after being out in the sun all day and we both worked up a pretty good sweat. She came out of the bathroom as I took my turn to shower. As I came out she was sitting on the bed naked brushing her hair. I walked over, dropped my towel and said, "How would you like an appetizer before dinner"? I gently pulled her head back and slid my semi erect penis in her mouth. As she was somewhat surprised at what I was doing it caught her off guard and she choked a little bit. She finally relaxed and start to slide her lips back and forth on my cock taking more and more down her throat. When she had my dick buried to the balls and it was fully erect she really started to pick up the speed. After a few minutes I could feel the cum building and a grabbed her head and exploded in her mouth shooting a warm load down her throat. She looked into my eyes as cum oozed down her chin and just smiled. She knows how good she is as a cocksucker and also knows how much I enjoy it. She slid my dick out of her mouth and said, "Now that's what I call an appetizer. We better hurry or we are going to miss dinner. More to come later, right."

I said, "Tonight I will return the favor. I think you will be my dessert."

We headed off to dinner and a relaxing evening. There was a Comedy Show in the auditorium which was quite funny and a little risqué. After the show we went to the casino for some fun and cocktails and then onto the deck to see the moon glisten off the water. It was a warm evening with tropical breezes so refreshing. It made for a very relaxed atmosphere and grandmother and I were very relaxed after a full day in the sun. As we sat on the deck talking I commented I was still hungry.

She asked if I wanted to go to the lounge for a snack. My reply was, "No I want to go to our room and have you for dessert as I promised earlier. I want to taste your juices and smell your aroma. What do you think?"

The next thing I knew grandmother was out of her lounge chair heading down the hall. She stopped and looked back and said, "Let's go fulfill your promise since I was hoping you hadn't forgotten."

When we got to the room and prepared for bed I got some almond oil from my shaving kit and a towel and placed it on the table next to the bed. When grandmother came from the bathroom to our bed I asked her to lie down on her stomach as I sat on the side of the bed. I slowly kissed her neck and back as I stroked the cheeks of her ass and her inner thighs. She became quite relaxed as I continued to stroke her smooth skin. I poured some oil in my hands and worked my way from her shoulders and neck down her back and stopped at the top of her cheeks. This continued for quite some time as her skin slowly absorbed the oil. Almond oil is great for massages as it absorbs well and is not too greasy.

I then moved to her feet and legs starting at the bottom and worked towards her thighs. The key is to be slow, be deliberate but take time to stroke all areas. As I worked my way up her body I could sense her relaxing and feel her body embracing my touch. She was sighing and in a state of bliss as I continued to stroke her inner thighs. I spread her legs and could see the wet spot in her pubic hairs and the aroma was intoxicating. I very slowly stoked her outer lips and her wetness was a natural lubricant. I played with her clit and she tensed. I did not want her to cum yet so I slid my middle finger deep in her vagina and ever so slowly moved it in and out driving deeper with each additional stroke. She was pushing back trying to take it as deep as possible but I still did not want her to cum. I would build her passion to a new level and then relax so she would come back down from her heights of ecstasy.

As I kissed her cheeks and stroked her pussy I asked her to roll over. She laid on her back and I put lotion on her stomach and legs to continue the massage. Her body was so relaxed but her mind was on edge. She knew and craved what was soon to happen. I spread her legs to gain access to my 'late night snack" and positioned myself to give me complete access to her swollen vagina. I licked so gently from to bottom to top slowly sucking on and exploring her clit. I continued this for awhile and she was getting more excited as I continued. When I felt it was time I slid my hands under her ass and lifted her cheeks off the bed and buried my tongue as deep as possible. She pushed back so hard and had a mind blowing orgasm and the juices flowed. I was swallowing as much as possible but it still ran down my chin. After a few seconds she went limp and collapsed on the bed.

As she laid there trying to regain her composure I slid up and position my stiff cock against her swollen vagina and slowly slid it in. She arched her back giving me more access to her and I was soon buried balls deep. I slowly pulled back and reentered her over and over always balls deep. She was so drained from her earlier climax she was limp so I picked up speed and finally emptied my load in her moist pussy. She sighed and locked her legs around me as I climaxed deep in her. Eventually she released her grip and we both collapsed on the bed......totally spent. It was so erotic, so arousing, so sensual. Wow, what a night; pure bliss.

The next morning we awoke to a bright sun flowing thru the windows. We decided to get moving and showered and dressed and then on to breakfast. A new port and a new shore excursion for sightseeing and exploring. This continued throughout the cruise as we were in a different country and city every day. The ship docks in the morning and the travelers have the option of going ashore to sightsee, shop or visit the local area. During the night the ship is traveling at sea to the next port. This continued on throughout our stay as we visited many countries and ports. We were finally completing our cruise and heading back to our debarkation port so it was our last night at sea.

Since it was our final night aboard the ship I wanted it to be very special. I had made reservations in the private dining room, a steakhouse for our last dinner. We had a quiet table in the corner and Grandmother and I dressed for the evening. She wore a floor length low cut gown that was stunning and I wore my new suit. We ordered dinner and I decided we needed to toast the evening with champagne. We were really going to make a night of it. Over dinner we discussed the cruise and the trip. We talked about the various ports we had visited and we also talked about our sexual escapades. We reminisced of the sensuous love making and during the discussion I asked Grandmother what she wanted for our last night. Her reply was nothing specific but let's just take it as it comes but make it ever so good and so natural not forced. I couldn't agree more.

After dinner we took in a show in the auditorium and then headed back to our room. I had picked up an additional bottle of champagne for our evening and as Grandmother was changing I popped the cork and poured two glasses. I was on the balcony enjoying the warm evening as Grandmother came out to join me. We were sitting on the balcony talking and enjoying the warm tropical breezes sipping champagne. I had changed into shorts and a t-shirt and Grandmother had on her robe. Grandmother stood up and was leaning over the balcony railing and I slid my hand up under her robe and as expected she was naked. As I caressed her smooth cheeks she bent over the railing for easier access to her cunt that was starting to moisten. I slid down my shorts and eased up behind her sliding my erect penis in her pussy. She pushed back to take the full length and we stayed like this for a few seconds. I very slowly slid my dick in and out to enjoy the time and she was getting very emotional.

We decided to move into the room whereby Grandmother went in throwing her robe to the side and climbed up on the bed on all fours. She said, "Come on David mount me and bury your dick in me like you own me which you do."

I proceeded to fuck her hard and deep and she pulled her head back as I pulled her hair towards me. She had her hand between her legs stroking herself as my balls were bouncing off her ass. I grabbed her hips and pulled her tight and my climax peaked and I exploded in her. At that time I could hear her moaning with an intense orgasm also. As my dick slid out you could see my cum seeping from her cunt. She rolled over and pulled me close giving me a passionate kiss. She looked in my eyes and said, "This cruise was all I was hoping for and more. Thank you for making me feel like a special lady. I hope you got what you wanted and needed."

My reply was, "Grandmother with you I feel like a man with a purpose and you really bring out the best in me. For that I will always be grateful."

With that we decided to go to sleep in each other's arms.

The next day was time to depart and head to the airport. It was time to return to reality and back to the real world. What a week , what a trip to remember. Grandmother and I said our goodbyes and headed home. I think I will be making a trip to visit in the near future; the real near future. I know I will be welcomed with open arms and........assuredly open legs!!!