Room Service Waiter Gets Great Tip

If you've read any of my previous stories, you know that my wife Jeanine is a very sexy and hot looking woman. Her long legs, nicely toned ass, tight abs, incredible breasts and gorgeous face makes any guy think about what it would be like to get her in bed. Fortunately for the last twenty plus years, all of those other guys could only wonder, while I got to experience it firsthand what a sexy woman she is in and out of bed. That was until a recent trip to a beach resort a month ago.

Jeanine and I decided we were going to take a few days off for ourselves while our older kids were home from college for spring break. It was a chance for us to get a few days by ourselves, without our two younger kids and it would give our older two kids a chance to earn some spending cash as our baby sitters for a few days when they were home.

We decided to stay fairly close to home and chose a nice beachfront resort on the ocean which was about a four hour drive for us. After spending a few days with the family when our college kids arrived home, Jeanine and I drove out late Sunday to the resort. I had a business-related call scheduled for early Tuesday morning, but the weather forecast for the next few days was supposed to be hot and sunny before thunderstorms later in the week, so we decided to go early in the week to get as much sun as possible.

The resort itself was beautiful. Besides being right on the ocean, it had a large pool area, nicely furnished rooms and large balconies from each room overlooking the ocean. We were both tired from the drive after a full day with our kids, so we quickly settled in to bed. Despite the fact that Jeanine was wearing some very sexy lingerie, both of us thought cuddling closely and getting a good night sleep was the right thing to do. Jeanine knew that I was probably looking forward to a good fuck session, but said she'd make it up to me the next day, which was fine with me as I was very tired. In addition to her sexy lingerie, Jeanine also put on a sleep mask which covers her eyes and allows her to get a full night of sleep, as usually she is a very light sleeper who wakes up at the crack of dawn.

After a good night of sleep, we woke up and decided that we'd order room service and enjoy it from our balcony. Jeanine was still in her lingerie when the room service attendant (Santos) arrived, but had gone into the bathroom. Without even thinking about it, I let the room service attendant in and asked him to put the tray on the table on our balcony. Imagine mine, Jeanine's and Santos' surprise, when she came out of the bathroom, not having realized he was there. She immediately said "excuse me" and quickly went back into the bathroom, but not before Santos was able to get an excellent view of my scantily clad wife. He had a smirk on his face as he left the room.

After apologizing to Jeanine for not letting her know that Santos was there, we settled down for a romantic breakfast on our balcony overlooking the Atlantic Ocean. We had decided that we would take advantage of the beautiful sunny day and spend it at the pool or beach, as you never know what the weather might have in store for us the next few days. Jeanine decided to wear one of her more revealing bikinis – the kind that she only wears for me when we are alone and there's no chance anyone either of us know will see her. It looked amazing on her. It was kind of a hot pink with lace yellow edging. The bottom was one of those Rio-cut types, kind of half way between a thong and a normal bottom. Up the butt crack, it had that scrunchy look, so it hugged her perfect ass very nicely. The top left little to the imagination, as the top halves of her areolas could barely be seen through the yellow lace material.

The cover-up that Jeanine put on was a white netting material, so although it covered some of the bare skin, she still turned a lot of heads as we walked through the lobby on the way to the pool area. Over the course of the day, my ego went through the roof as I watched guys of all ages check out my hot wife. The pool was very refreshing and since they had pool-side bar & food service, we decided to stay there all day. As it turned out Santos, our room service attendant from breakfast, was the waiter who had coverage for the pool area that afternoon. Since Jeanine had barely even seen him, she did not realize it was the same guy until I commented that it was his lucky day to first be able to see her in her skimpy lingerie and now getting to see her in her skimpy bikini. At first she seemed a bit uncomfortable after hearing that it was him who saw her earlier, but after a few Mimosas, she was more relaxed and we just enjoyed our day together in the sun.

Watching the reactions of guys as she walked around the pool deck or emerged from the water instantly gave me a hard-on. She even played along as a bit of a cock tease, when she slowly took her time while reviewing the lunch menu, fully knowing that Santos was memorizing every square inch of her body while standing next to her waiting for her to decide. As he walked away, she asked me if I thought she had given Santos a boner. I just responded that she was giving every heterosexual guy out there a boner.

After cleaning up, we went on a dinner cruise that had a fabulous dinner, drinks and dancing. By the time we got back to the room, it was after 11 pm, but both of us had been looking forward to a great fuck session all day, so as soon as we were in the room, I had my naked wife lying on the bed while I dove between her legs to suck on her completely shaven pussy. After a great fuck session of just raw passionate sex, we each took a quick shower and went to bed. Much to my delight, Jeanine was again wearing her sexy lingerie and sleeping mask and as we were about to fall asleep, we agreed that room service on the balcony would be a great way to start the next day once my business call ended.

I woke up at 7:00 to get ready for my business call which began at 7:30. Since the call was scheduled for an hour, I decided that I would order room service before it began and just ask them to deliver the food sometime shortly after 8:30, which would give me time to finish the call and wake Jeanine up if she had not already woken up by then. I knew that she would probably easily sleep that long, due to our late night and the fact that she had about three times the normal amount of alcohol that she'd usually consume the previous day. I decided to make the business call from the balcony, as it would not disturb Jeanine if I pulled the door and curtain closed behind me.

About half way through the call, another topic was brought up which required immediate attention, so we all agreed to just extend the call another 30-60 minutes, rather than scheduling an additional call for later in the day. So, with the change in plan, I quickly wrote a note out for the door to let whoever delivered the room service know to use their key and that they can just place the tray on the desk and I could sign the bill on the balcony. I placed the note on the door shortly before 8:30 and returned to the balcony.

There was a small opening in the curtains allowing me to occasionally look in to see if Jeanine had woken up yet. I happened to be looking in when to my surprise, Santos came through the door with our breakfast. I assumed he would place the tray on the desk as my note had instructed then join me on the balcony to get my signature. He placed the tray on the desk, but rather than join me on the balcony, he slowly moved back across the room to get a better look at my hot wife in her sexy lingerie. Normally, Jeanine sleeps with the blanket pulled up to her chin, but it looked as if she had gotten too warm, so the blanket was not covering her right leg and most of our upper body as it was sort of draped diagonally across her sexy body.

Santos had one of those pocket flash lights that he used to get a better look at her. I figured that he'd check her out a bit and then come and get my signature. He pushed on the bed a bit, apparently trying to determine how soundly she as sleeping. Santos then glanced over at the balcony and began walking towards it to I assumed get my signature. But rather than opening the sliding glass door, he instead peaked through the small crack that I had just moved away from and pretended to be totally engrossed in my phone conversation, and then I heard the distinct sound of the sliding door being locked. When I went back to the small opening, Santos was already on his way back across the room. At this point, I thought about pounding on the door, but then felt that watching him check her out was actually a big turn on for me, so I would let him do that since it seemed pretty innocent.

As I watched, Santos became a little braver as he slowly lowered his hand onto Jeanine's right breast. After giving it a light squeeze without Jeanine moving, he placed his other hand on her left breast and began to rub them gently. It was at this point that he decided he wanted a little more light, without having to hold onto his pocket flash light, so he went to the bathroom, turned on the light and then closed the door most of the way. The result was enough light showing across Jeanine's body, giving both Santos and myself a good view.

He returned to the side of the bed, where he again appeared to check how deeply she was sleeping by pushing on her arm to see if she would stir. When she was clearly sound asleep, he decided it was time to see her magnificent breasts. The lingerie she was wearing made it easy as there was a single tie in the front between the two cups that once untied allowed you to completely open up her top. He gently pulled on the string and then was careful to slowly remove the cups off her breasts. I honestly figured that's when she would wake up since she is such a light sleeper, but then figured the booze from the previous day was really having an effect on her. Again, I thought about pounding on the door to scare him off and wake her up, but I found myself getting very turned on by Santos checking out her incredible body.

Santos gently placed his hands on her bare breasts and once he seemed comfortable that she was still soundly asleep, he began to rub and squeeze them. After a few minutes of that, he lowered his mouth onto her right breast and began to suck on it. Santos was getting much more comfortable from her lack of response and began to get a little more physical with his squeezing and sucking of her breasts. When he momentarily stopped sucking on her right breast, it was clear that it was getting her aroused as her nipple was clearly rock hard and her areola was puffed out a bit as they get when she is getting aroused.

Santos appeared to notice that as well, as he moved to sucking on her left breast. It was at that point that Jeanine finally stirred. It startled Santos, but all she did was raise her hands over her head into a position that looked as if she were tied down or her wrists were being held. That's when I realized that she was now awake at least at some level and was thinking that I was working on her body. Since we occasionally do light bondage with her being blindfolded and her wrists being tied or held loosely above her head, she was acting that out by putting her hands above her head.

I'm not sure if Santos figured it out or not, but he definitely took that as a sign that she wanted him to continue his assault on her body and he began to maul her breasts with his hands and mouth. Over the next few minutes, Jeanine's breathing definitely was picking up, as you could she her tits raising and falling with each breath she took. Santos had begun to kiss and lick his way down her tight abs, as my business call finally came to an end. I thought to myself how far am I willing to let this go AND how would I possibly explain it if Jeanine realized it was not me and that I was on the balcony. I decided that I was OK with him doing anything but fucking her, and that as long as he left on his own, she'd never need to know that it was him. As far as she knew, it was me that was having some early morning fun with her tight body.

As he got to her panty covered pussy, he began to rub her pussy through the lacey material. He slowly slid the material to the side exposing her engorged pussy lips. He immediately went to work on her pussy with his tongue, while pushing the remaining blankets completely off of her. As he was probing her pussy with his tongue he raised his hands to continue his assault on her perfect breasts by squeezing them and rolling her perky nipples between his fingers. Jeanine was clearly pushing her pussy lips to meet his probing tongue as she was becoming very aroused. Her hands remained above her head, as she was playing out the fantasy of being forced upon and the fact that Santos had just pushed her panties to the side instead of taking them off, played well into that fantasy.

When Santos momentarily picked up his head and looked over at the balcony, I moved away from the crack in the curtains for a few seconds. When I returned to peer into the opening, Santos was in the process of removing his clothes while fingering Jeanine's pussy. I watched in amazement as Santos' perfectly toned body came into view and when he dropped his boxers, his near perfect cock was also on display. It wasn't necessarily huge or anything, but it was perfectly straight and was probably about 1-2 inches longer than mine and definitely had more girth. I watched as he slowly stroked his cock with his left hand while fingering Jeanine's pussy with his right hand. As Santos was climbing onto the bed between Jeanine's spread legs, I was about to pound on the door and end this, but then I noticed that my own cock felt as if it was going to break out of the shorts that I had on.

So, rather than stopping Santos, I dropped my own shorts and began to rub my own cock as Santos moved his cock towards Jeanine's waiting pussy. Rather than plunge it deeply into her boy, he actually started to dry hump her while continuing to hold her panties to the side. His strokes were long and slow as he slid his cock from the tip to the base across her pussy lips. He continued doing this for what seemed like hours just sliding his cock back and forth across her engorged pussy lips. With his free hand, he groped Jeanine's left breast and used it to maintain his balance as he continued dry humping her with his magnificent cock to her exposed pussy lips while he held her panties to the side.

I was trying to hold off my own orgasm as my hand frantically worked my own un-lubricated cock. When Santos shifted his positioning, I assumed it was time, as he once again lowered his cock along Jeanine's glistening pussy lips one final time. He lined up the impressive head of his cock to her waiting hole and began to push his way into her tight body. Suddenly Jeanine reacted as if something was wrong and was moving her hands down to her sleeping mask to see who was beginning to fuck her, when Santos quickly reached up, grabbed both of her wrists and gently placed them back over her head. To my surprise, she seemed to take that as some kind of sign that it was ok and Santos began working his impressive manhood into her tight pussy.

Santos was again very slow and deliberate with his motions, pulling his cock all the way out before realigning it and sinking it a bit deeper. He continued to do this until he had the entire length of his cock buried in my wife's pussy. Once he was completely in, he stopped moving for a few minutes while he again lowered his head and hands to her tits. When he resumed fucking her, Jeanine was clearly trying to speed him up be grinding her pussy against his cock and attempting to wrap her legs around him to pull him closer. Santos continued his assault on her pussy and began to speed up, although he continued to have long deep strokes by nearly pulling completely out with each stroke.

After a few minutes of this, with Jeanine's chest thrusting forward from her deep breathing and her head going from side to side, Santos worked up to a furious pace. He was slamming his cock into Jeanine with hard strokes. Within minutes he arched his back as he grabbed onto her tits and must have shot his load deep inside of her. About that same time, I was shooting my own load onto the balcony and trying to catch my own breath. I watched has Santos slowly pulled his cock out of Jeanine's pussy and climbed off the bed. As he was getting dressed, he took out his cell phone and took a picture of my wife's incredible body with his cum trickling out of her still open pussy.

He walked to the balcony and undid the lock on the sliding door, tore up the bill and left the room. I was nervous as I went into the room and climbed onto the bed with Jeanine. She was still breathing heavy as I lifted her sleeping mask. Jeanine smiled at me and said thank you for the very nice surprise. When she asked if she could reciprocate and give me a blow job since her pussy was very sore, I told her that it was not necessary since I was quite sore myself from jerking off without any lube.

I never told Jeanine who it was that delivered breakfast to her that morning, she never asked and over the next few days at the resort I never saw Santos again. To be honest, I don't know what I would have done if I had, but figured he at least owed me a big thank you for allowing him to fuck the hottest MILF on the planet.