Iss Me Ate

**Disclaimer: Let me first state that this story is real and took place roughly twenty years ago. If you are looking for a story to get off on in quick fashion, this story probably isn't for you. While it does contain everything one likes to read about on Literotica, it is slower in the build up to that point. It's my first story I've ever written, so don't be too hard on me😊. All the people in this story are age 18 or older.

------------------------

My name is Bruce. The week in Boston has been beautiful. My meetings went well and now I have a few hours to shop before the stores close. Kate will be meeting me here at the Boston Marriott Copley Place tomorrow morning. It will be just over a 4-hour direct flight for her. I'm shopping because I told her not to pack and I will buy her the clothing necessary for the next 24 hours of activities. Twenty-four hours are all we have together as she can only manage one night away, on such short notice.

I was only half-way joking when I asked Kate to fly out at the last minute to share some time with each other. We have only known each other for such a short time and only met in person one time when we had a business lunch meeting in Chicago. The attraction was immediate. We have stayed in touch, off and on, with each other, going on six months now.

I finished my shopping just as the stores were closing. I have meticulously selected a wardrobe that will be fitting for Kate and for our 24 hours together. I arranged a town car to pick her up from the airport and drive her to the hotel. I left a key pass for her with the concierge in the lobby. Upon her arrival, she would pick up her electronic passkey and proceed to meet me in my room -- Room 2801 to be exact.

We did not set an exact meeting time, as the flight may be unpredictable. Late morning was the best guess at when she would arrive. As I waited for Kate (starting at 6:00 a.m. because I couldn't sleep), I began to get butterflies in my stomach, similar to when I was a teenager, or similar to the feelings I get before I would present a big budget proposal to the hospital board. Why was I so nervous?

At 11:10 a.m., the familiar sound of the electronic locking mechanism on the door could be heard. About 50 thoughts went through my mind in the instance it took Kate to insert the card key and open the door. "Should I stand? Should I sit? Should I look surprised? Should I jump up and greet her at the door? Should I be aloof....." Before I had any time to react, Kate had cautiously stepped into the doorway, wanting to make sure she was in the right room. The look on my face must have been quite a sight as I was still sorting through all of my "should I's" and "shouldn't I's".

We stared at each other for what seemed like several minutes. Kate, with a sincere smile on her face said, "Hi Bruce, I've missed you". I just smiled and put my arms around Kate and held her tight. All the feelings came rushing back. Maybe l had forgotten how good l felt when we were together. Maybe l wasn't as invincible as l thought l was. Maybe l needed to have for my life exactly what I felt that very moment. My mind was quickly brought back to the present as Kate began to lightly tickle me. My only defense was to grab her and throw her on the bed and playfully wrestle with her. Without much effort on my part (I think she let me win) I subdued her, and then were able to lay side by side.

Our first kiss was surprising to me. The kiss was much more intense than I had ever imagined it to be. It was very easy to tell that both of us had looked forward to this experience for such a long time. So many of those pent-up thoughts, feelings and emotions were released in the next few minutes as we kissed and held each other. As good as it all felt, I had so much planned for us and so little time to do it. It was now 11:30 a.m. and she still hadn't changed in to her first outfit I had purchased. As she lay on the bed, I laid out her first set of clothes that would be needed for the afternoon's activities. One agreement was made first. I get to watch her undress and then get dressed into each outfit. I find this quite erotic. Once again, she shocked me by agreeing to the terms!

I watched her remove the clothes she had been wearing. Not too surprising, she seemed a bit shy and nervous. She was wearing sweats that were comfortable for the flight. When she removed her shirt, she began to play with me a bit as she had a t-shirt on underneath. I was expecting to see her in a bra. She could tell I was just a little disappointed. But she didn't mind, she actually kind of enjoyed it. "What's wrong Bruce, expecting to see something else?" I must say, even in just her t-shirt, I thought, "what incredible breasts she has". I could see her hard nipples through the white t-shirt. I reached out and casually tried to touch them, but she brushed my hand away. All she said was "not yet". I wasn't sure what this meant. I had hoped it was not a harbinger of how things would continue.

To my surprise, Kate turned her back to me and removed her shirt and then quickly removed her bra. Before I could say much of anything, she had quickly slipped on the bra I had purchased for her. It was just a simple cotton bra that was fairly thin. I had purposefully picked this bra out, as I wanted her to be comfortable for our afternoon activities, and hopefully see her nipples poking through the shirt. With her back still to me, she bent over and removed her sweatpants. She then bent over once again and slipped off the panties she was wearing. She had a perfect and tight ass. I dreamt about grasping each globe in my hands. As Kate bent over, to slip on the matching cream panties, I could see a slight glimpse of her shaved pussy. Oh my, what thoughts this brought up. It was a very quick and fleeting thought as Kate pulled the panties up around her waist. I picked out panties that would once again, be comfortable, but at same time outline and compliment her incredible ass. What had l been thinking? I had this beautiful woman on the bed, and I suggested we get up and get going. I must have been an idiot!

Kate pulled over her head the white tank top and slipped on the tan shorts. After her socks were pulled up, she put on the Nike hiking boots I had purchased. Kate was now set for the first round of activities. All I could think about was how much I wanted to make love to her or fuck her, but I didn't know if that was in the cards for us at that point. She had to know I was thinking this. She relished in the bit of control she had over me.

We walked over to Copley Plaza and went down into the subway terminal to board the green line. In such a simple outfit, Kate was incredibly sexy. As is often the case, there were no seats, so I leaned up against a support pole. Kate had her back to me. She leaned against me and used my body for support. My left hand held on to the pole, while I wrapped my right arm around her waist and laid my hand flat on her stomach. My thumb could just touch the bottom of her bra through her shirt. I pulled her ass tight to my crotch.

As the subway jerked to a start, there was an instant sensation as I could feel the pressure of her amazing ass pressing against my mid-section. She just turned and smiled at me. Surely, she had to feel my hard cock pressing against her ass. I was quite shocked by the pleasure I received over the next 10 minutes as we rode to the Government Center. The motion of the subway car created the most erotic feelings as her ass rubbed up and down against my cock. When the subway finally came to a stop, I was so hard and starting to get wet. I didn't want to move. The vision of the scene from the movie "Risky Business", when Tom Cruise had sex on the subway. This was all very vivid in my mind! If I ever got her alone and all to myself, sparks would fly. I knew that would be the case. We had sight-seeing to do, although, I could have done without it at this point, and just fucked her in all positions possible.

We walked from the Government Center to Faunal Hall and then over to the shops at Quincy Market. We walked around the shops and then got some ice cream. The time had come. It was time for the Freedom Trail. The Freedom Trail takes you through all the historic sites in and around Boston. I was exhausted, but somehow, Kate dragged me along the route. We saw the Boston Tea Party site, the Old North Church, Paul Revere's House, the Granary Burying Yard where several famous people are buried, the USS Constitution, Boston Massacre site, the Commons, Beacon Hill and many other places. We had a wonderful time. I enjoyed being able to walk and talk with her while we held hands. An occasional pinch of her butt was also an added pleasure. I think we could have been touring a dump site, and as long as I was holding Kate's hand, I would have loved it.

We took a cab back to the hotel. I would have preferred another subway ride, but we didn't have the time. We needed to get cleaned up and changed before hors devours were served on the Concierge level at 4:30 pm. We only had about 45 minutes to shower and be in the lounge. I had been watching Kate all day and all I wanted to do was take a shower with her and fuck her as she leaned forward, with her hands against the wall, while I entered her from behind. Following that, I just wanted to lay in bed, holding each other, completely naked!

I watched her get undressed and she didn't seem to mind at all this time. I sat on the edge of the bed as she changed. Kate came over to me with just her underwear on. I wrapped my arms around her waist and held my hands on her ass. I laid my head on her chest between her tits. I gently kissed between her boobs. I could taste the salt from her perspiration. Talk about an aphrodisiac. It was incredible! I gently kissed each of her boobs and sucked on her now hard nipples, and then I just held her. I was so content. I could have stayed there for eternity. In that position, I felt safe, secure and I could feel the same from Kate. This too wasn't to last as she pulled me up and led me into the shower. She started the shower and climbed in as I undressed to join her.

I lathered Kate's back with soap and gently massaged her. It felt so good to be touching in any way possible. She pressed her back to me and nestled me tight against her. She laid her head back and rested her cheek against mine as we started kissing. My cock was so hard as it literally laid in the crack of her ass. She began to move her ass in different motions against my cock. I didn't think it was possible for my cock to get any harder. I was wrong. Once again, I took the soap and lathered the front of her body. I took great care as I gently touched her. I rubbed the soap on Kate's tits and paid particular attention to her hard nipples. I was so turned on. She turned her face towards mine and kissed me very lightly. Each subsequent kiss became more intense. Finally, our tongues began to search each other's mouths fervently. I had wanted to kiss her like this all day. For the last several hours as we walked, I was reflecting on everything I enjoyed and loved about Kate. Did I really say "loved". I'm not sure where that came from, hopefully from my heart. I don't think I've felt that way before with any other woman. All of these emotions seemed to be coming out now as I held Kate.

With the soap still on her body, she turned around and we continued to kiss. The water was pouring down on us. It was all so intense. I held her ass, but this time I pulled her tight against me. I wanted to have my cock in her pussy, right then, and there. I felt like this day had been nothing short of foreplay for us.

Reality kicked me in the butt and reminded me we were going to be late. Thank goodness Kate had more willpower than I did. Reluctantly, we turned off the shower and I stepped out first, got a towel from the rack, and wrapped it around her. One last time for now, I was able to hold her. I held the towel around her front and gently moved her wet hair aside and kissed the side of her neck.

We quickly dressed and got ourselves ready for hors devours. I wasn't sure what she'd think of her next outfit, but it was all she had, so she had no choice. I guess she could have worn her shorts. I laid out for her a pair of sexy black panties with a matching bra. The bra was very thin and was not able to contain her amazing nipples. I picked out a casual, yet sophisticated, straight leg black trouser, a tight white turtleneck which accentuated her beautiful breasts. Finally, I bought her a checked women's suit jacket. Once again, comfortable shoes were in order, so I got her a pair of black Cole Haun loafers. As expected, Kate looked beautiful.

The Hors Devours and cocktails were delicious. The view of the city was spectacular as we sat and talked. More than anything, I just wanted to take advantage of every minute I had with her. There was no time to waste. We sat across from each other. I don't think we took our eyes off each other a single time. I treasured every one of our kisses we were able to share.

After Hors devours, we had about an hour to change into our dinner clothes and go for a walk. This change was very simple for Kate. She removed her trousers and replaced them with a very sexy A-Line skirt. Her body is so firm. I wanted a skirt for Kate that was tight fitting to complement her shapely ass. The skirt was fairly short so as to accentuate shapely long legs. She took the turtleneck off and replaced it with a white silked button up shirt. She put the jacket back on over the shirt. I had one request. I asked her to go without her bra and panties. To my delight and pleasure, she obliged. Finally, a pair of Bandolino Ankle Straps completed the ensemble. Kate looked stunning which came of no surprise to me. It was an honor for me to accompany her.

Before our reservations for dinner, we were able to take a walk through the Boston Commons and then go for a ride on the Swan Boats. The Swan Boats have always been one of my favorite things to do in Boston ever since reading the children s book "Make Way for Ducklings". The setting for this book is the swan boats. As the man paddled the boat around the pond, it was a perfect time to just hold Kate and reflect on the amazing day we have had together thus far. I gently touched and played with her hard nipples from time to time. She was getting very turned on as her nipples became more pronounced.

We walked down Boylston Street, hand in hand, to the restaurant Legal Seafood. We had a very romantic and candlelit dinner. Legal Seafood is famous for its Filet Mignon and Lobster, so of course we dined on that. The dinner was perfect and concluded with desert of Tiramisu. Kate looked so sexy. I could see her brown areolas and lighter colored nipples through the white silk shirt. Good thing she had a suit jacket to wear over the shirt when necessary.

So far, the day had been perfect. After dinner it was time to return to the hotel and change one last time for our night out on Broadway. There was no coincidence that I bought tickets for Miss Saigon. Not only is it one of my favorites plays, but the show, in a way, kind of paralleled Kate and me. The music was quite electrifying, and at points, brought tears to the eyes of many. Overall, it is a very sad play.

Ever since I've known Kate, I have wanted to take her to a Broadway play. So, guess what? We walked back to the hotel with our arms around each other. Kate changed into her last outfit of the evening. This was my favorite outfit as I took great care in picking this one out.

Her evening dress was a shimmering black penne velvet halter dress with glimmering drop diamond earrings. I had waited so long to see Kate in this dress. She was so elegant. Finally, Anne Klein ankle wrap stilettos matched the dress perfectly. The shoulder less dress showed off her incredibly sexy tanned shoulders. The dress was full length, but yet, slit up just inches from her ass. I didn't feel like I was worthy to be with her. Kate was stunning. I loved how she had every man's attention as we walked by them.

The story line and music held us mesmerized the whole time. Two songs from the show will always remind me of Kate. The songs are "Sun & Moon" and "I Still Believe". I held Kate especially close to me during these songs. I also loved to see her cry and allow herself to be so vulnerable in front of me. I couldn't hold back watching her. My own eyes had become moist also.

I knew at that point I was sincerely falling in love with Kate. I couldn't help but wonder if she was crying for the lovers on stage which might never be together again, or the thoughts that she & I will, quite possibly, never spend another day, and night, together like this day. We didn't know, but we hoped. After this day, I find that very hard to believe that we won't be together again. I still have so many places I want to share with her over time.

I didn't want this night to end. We took a taxi back to the hotel and then decided to walk the last couple of blocks. I wanted to walk with Kate and hold her hand one more time. I was so honored to be with such a beautiful Lady! l wanted everyone to see her!

It was about 12:30am when we arrived back at the hotel. Dessert was being served on the concierge level, but we decided to pass and just return to the room to spend the night together. By now, I was so turned on and horny that all I wanted to do now was hold Kate and make love to her. The sexual energy between us was so thick that it could be cut with a knife. As I held Kate close, and kissed her, I unzipped her dress and let it slip to the floor. My God Kate...she was so beautiful. There she was in front of me wearing nothing. I gently picked her up and carried her over to the bed. I lay beside Kate, and we continued to kiss passionately. Fourteen hours of foreplay was now going to culminate in something truly beautiful.

I removed my suit and lifted her on top of me. As we kissed, the feel of my cock against Kate brought back memories of our earlier subway ride. There was now just one difference. She was laying there with me nude and l was going to make love to her. I purposefully said make love because I could tell that is what both of us desired at that point. I didn't want to fuck Kate right then. There will be plenty of time to fuck her later. I was going to make love to Kate now. I had noticed earlier in the day, as she changed clothes, she had a beautiful, and cleanly shaved pussy.

As we lay there kissing passionately, I moved my mouth to her tits and proceeded to alternate between each of her nipples. I sucked and nibbled on both nipples as we laid together. Our legs were intertwined. I moved my knee up to her pussy and she pushed her pussy back in to me. It was easy to tell that this was turning her on. The whole thing was turning us on. Kate began to slowing start stroking my cock. Her breathing became more sporadic as she moaned. I wanted to have my cock in her pussy so badly, but first I had some other things to do which would delight both of us. To tell you the truth, I think she kind of enjoyed knowing how much anxiety this was causing me!

I rolled Kate on her back and with increased force, I licked from her nipples to her inner thighs. Kate was already wet. The smell and taste of her pussy was incredible. All I could think about now was how much I wanted to fuck her pussy with my stiff tongue. Her clit was so hard I could tell what she wanted. I positioned myself between her thighs and sunk the length of my tongue deep in her pussy, as I continued to rub her clit. I gently rubbed all around her clit. I could tell she wanted more. I began rubbing my tongue on her clit vigorously, while inserting two fingers in her pussy. Her pussy was so wet. I knew she wouldn't last long.

It took no more than a minute. Kate began to moan more loudly. Kate's whole body shook. Her body became completely tense and ridged. At the same time, she arched her back very tightly against me, as if her life depended on it. She let out a moan indicating her first orgasm. I could feel her muscles in her sweet pussy tighten on my tongue. This was followed by her sweet pussy cum. It all engulfed my mouth, tongue, and fingers. I literally watched her orgasm ripple through her body, leaving her completely void of energy.