I met Jan when she was a kid. My wife, Sharon, and I had chaperoned many of her school functions and as Jan grew older we developed a big brother little sister relationship. I was her confidant through her first crush, her first date, a plethora of boyfriends and the first time she had sex. When Sharon and I had our first child, Jan was our babysitter. She was a cute teenager whose personality won over everyone she came into contact with. In spite of the nature of our relationship and fifteen year age difference, her hot body had not escaped my notice.
When she left for college we remained close, talking occasionally on the phone. She came over for dinner when she came home and we even became drinking buddies. Although my wife’s relationship with Jan was extremely close, Jan had not involved her in the details of her life.
Just before Christmas vacation, Jan called Sharon and asked if she could come over during the break, explaining she wanted us to meet someone. We arranged to have Jan and her friend over during the holidays.
The night of our arranged date, I cooked a nice dinner. When Jan and her friend, Rob, showed up we had a drink before dinner and had a chance to get to know the young man. He was a graduate student at Jan’s college who had done his undergraduate work at an Ivy League university. Rob was about to finish his MBA and had accepted a position with a major corporation in a management trainee program. He was a tall nice looking guy who obviously made Jan very happy. We polished off the bottle of wine they had brought with dinner and went into the living room to have after dinner drinks. Jan nervously downed a couple of drinks and looked us into our eyes and announced. “we haven’t told anyone yet but Rob and I are getting married this summer.” After a brief episode of hugging, we drank a toast to their impending marriage. Jan had managed to get a bit drunk and Rob said he needed to get her home. As we hugged goodnight I felt extremely happy that Jan had fallen in love with such a great guy but I also felt a little jealous.
Sharon and I had always been very different people. She was the class genius and I was the hell raiser. We met after she had experienced a painful breakup and I was taken with her neediness. She was impressed with my “man-about -town” image and we got married after dating a short period time. Sharon was a great mother to our two daughters but our differences proved to be too great to reconcile. Right after the holidays, we agreed to divorce. Early the next year my company offered me a job at the corporate headquarters. This job was considered to be a gateway to upper management and too lucrative to turn down. I made a deal to assure that I was able to spend a week in my home area every two months and accepted the position .
Jan had planned a June wedding in our hometown and my ex-wife was having a great time helping out. I had scheduled a vacation for the week of the wedding. Sharon and I offered to throw a party for both families and all the out of town guests who were arriving early. The Thursday before the wedding we all gathered at a local club that I had reserved for the evening. I hired a blues/jazz band to appeal, at least some, to all four generations that were represented. The food was outstanding, the liquor was flowing and everyone seemed to be having a great time as the night proceeded. I danced with Jan a few, probably too many, times. She seemed a little different, seeming preoccupied when we weren’t dancing and a little too aggressive when we danced. At one point, while dancing I had become semi erect. Hoping she wouldn’t notice, I lost my breath when she ground her crotch into mine. The party went on until midnight. The younger folks were going to the bar of the hotel which was serving as the headquarters of the wedding. I was staying about three blocks from that hotel in a restored hotel that was originally built in the late 1800’s. I excused myself from the after party by saying, “I’m not as young as you guys.”
Walking through the lobby of my hotel, the bartender called out, “we have that Lagavulin you asked for earlier.” I walked over to the bar and said, “pour me a double and I’ll take it up to the room with me. That should get me to sleep.” I took my drink and went to my suite. The suite was a remarkably beautiful room with an office and sitting room on either side of the bedroom. The sitting room and bedroom were beautifully decorated in the period of their original construction. The dark hardwoods of the office hid its technologically advanced features. Contained in the office were all the advancement my office in the city had.
I loosened my tie and sat down at the desk to check my e-mails and faxes. Finding little of a pressing nature, I turned on the news a leaned back to enjoy my Scotch. In a few minutes I took a shower and prepared for bed. As I showered I tried not to think about Jan’s cute little ass and the way she had ground against my dick as we danced. Each time I thought about her, my cock would swell and I would remind myself that she was getting married on Saturday. As I got into bed, the Scotch put me out of my misery as I quickly fell asleep.
My cell phone woke me from my sleep later. Jan’s voice on the other end asked, “can I come over?”
“Sure,” I responded not knowing what to expect. In about 20 seconds I heard a knock at the door. She had called from the elevator.
As she stepped into the room, she threw her arms around my neck. She allowed her coat to slide to the floor revealing a black camisole. As she passionately kissed me, my mind raced. Is she drunk, is she kidding or am I dreaming? As she pushed me onto the bed she whispered, “I’ve always said that if you were ever single I was going to fuck your brains out.”
“You are getting married Saturday,” I protested.
“We are both single tonight,” she reminded me.
As we fell to the bed, she removed my robe leaving me in just my boxers. We lay side by side and shared the deepest kiss I had ever experienced. Her tongue lead me to believe she hadn’t told me about all of her sexual experiences. I removed her camisole to reveal to breasts that were much larger than I had noticed. She guided my face towards her nipples as they hardened and lengthened at the touch of my mouth. She began to moan as I changed from one breast to the other and she reached into my shorts and grasped my cock. Her legs stiffened as her stroke ran from the base to the head of my dick. “Fuck me”, she screamed as my tongue slid down her flat stomach. I kissed down her thigh till I reached her knee and switched to her other leg. Her breathing became shallow as she arched her back, grabbed my hair and pulled my face into her pussy.
As I traced her lips with my tongue, I could feel her moving towards a powerful orgasm. As I flicked her clit and began to tongue fuck her she released a torrent of juices that flowed down my face. She screamed and arched her back as she moved one leg over my shoulder. As she ground her clit into my face I realized my work there would continue a while. I slid two fingers into her beautiful pussy and softly rubbed her most sensitive spot as I sucked her clit. She was lost in a series of orgasms. I began to work my way back up her body. As my tongue reached her nipples she began to groan and whispered, “fuck me now.” While licking her nipples, I positioned myself between her legs. She grabbed my dick and positioned it at her opening as she pulled me into her pussy. The warmth and wetness of her pussy was unlike anything I had ever experienced.
I thrust my self into her and began to slowly slide in and out of that amazing space. She completely wrapped my cock with warmth and I felt every side of her, She began to frantically buck as she approached another orgasm. As wave after wave of pleasure racked her body she was screaming loud enough to be heard in the lobby. She had gone a little limp on me so I flipped her onto her stomach and entered her from behind. I began to fuck her as hard as I could when I felt a feeling deep in my balls indicating my orgasm was on its way. As my cum came shooting out she was moaning softly and smiling. I shot five streams of cum into her before collapsing to top of her. As we lay there still connected she whispered, “I knew it.” After lying there for a few minutes I rolled her off of the “danger zone” and fell asleep with my arms around her.
The next morning I woke up alone. That night I attended Rob’s bachelor party and Sharon and I were included in the rehearsal dinner on Friday and of course, the wedding on Saturday. Jan’s eyes met mine a couple of times during the festivities but we did not speak a word. At the reception, Sharon and I were dancing when Jan cut in. “You were absolutely amazing”, she whispered before kissing me on the cheek. I returned the kiss then went back to the hotel and left for the city. In spite of geographical separation, we remain good friends………………………..