Born Again Virgin Loses It Again

My wife and I were High School sweethearts. After graduation, I went to college out on the west coast and she attended a local university in Ohio. But we kept up our long distance relationship through college and after we both graduated, I moved back home and we dated seriously for about a year before we got married.

Believe it or not, we were virgins on our wedding night. Oh yes, we had done some heavy petting over the years...lots of finger fucking and hand jobs and eventually, great oral sex. Many times after a long day of spending fun time together, we would go back to her place and I would peel off her jeans and eat her to an orgasm and then she would take out my cock and suck me off.

I remember the first time she took my cock in her mouth. At first, she really didn't know what do with it but as she started to observe my satisfaction by my moans, she started to do it right. First she licked my shaft like a popsicle, then she worked her way down to my balls and took them in her mouth one by one, so gently. When she kissed and licked the area between my balls and my ass, I felt my orgasm building.I told her that I was going to cum and so she moved up and took my cock back in her mouth....I told her I was getting close and I expected her to pull my cock out of her mouth but instead, she started to deep throat me. I have always been a big cummer and so when I started to unload in her mouth, I expected her to spit it out but instead, she swallowed it all and afterwards, she kissed me and stuck her cum covered tongue deep in my mouth.

I was a little shocked, but it was the least I could do for her after the way she had just blew my mind. We repeated this experience every time we could during that year we were engaged. But I guess because of our Catholic upbringing and the fear of getting pregnant, we never went all the way and it just reached a point where it just seemed like a great idea to save intercourse for our wedding night.

Our wedding night was extra special....the sex was a true act of love. We did some petting and I kissed my way down to her pussy and she started to moan. Just like I had done so many times before, I flicked her clit with my tongue, dove it deep in her cunt and then came out and sucked it like a little penis in my mouth. She told me that she was getting ready to cum but that she wanted my cock in her for the first orgasm of our married life.

So I got up and put my cock at the entrance to her womb and kissed her and said, let's consummate our marriage. We fucked slowly at first, but then we started to go at it fast and furious....deep and hard. She was rubbing her clit while my cock was going in and out and soon, she told me she was cumming and to not hold back. I didn't and we both exploded and then collapsed in each other's arms and fell asleep, deeply in love.

Almost nine months later to the day, our daughter was born. She was the love of our lives....the perfect child and as she grew older, she gradually developed the inner and outer beauty of my wife. She was good in school, loved sports and when she grew older, was a star on the high school soccer team.

We never had other children. It wasn't for a lack of sex. We always made love several times a week and always added a little adventure to keep the sexual part of our marriage alive. For instance, every now and then when our little girl was younger, I would get home from a week long road trip and my wife would meet me at the door in an over coat. We would go out to McDonald's so I could re-connect with my daughter. Then we would drop her off at my parents for the night and we would go home. I knew that all she had on under the coat was her fuck me push up bra and her thigh high stockings. On the way home, I would finger her wet cunt in the car and by the time we got in the door, she was sucking my cock and we would fuck our way to the bedroom.

When it came to sex, she loved to be submissive at times. After the usual kissing and cuddling, we would advance to oral....she would suck me first and I would stop her before I came. Then I would kiss my way down to her shaved pussy and eat her to orgasm. She would always tell me that if I made her cum with my tongue, I could choose the hole/s to fuck her. Most time, I would oblige by fucking her in the mouth, cunt, and ass in that order. She would even let me pull out of her ass and fuck her mouth until I came. She was just that way. She was the classic "lady on the street, slut in between the sheets" lady.

She never got pregnant again and when she turned 40 and our daughter was in high school, we decided that I should get a vasectomy. Although we had always wanted another child, it was just too late.

We lived a perfect life...almost a fairy tale but just like in the stories, fairy tales don't always come true.

My fairy tale life came to a bitter end one rainy night when my wife and daughter were hit head on by a drunk driver on the way home from soccer practice. By the time I got to the hospital, they were both gone and a few days later, I buried the two great loves of my life.

Life after their death was a daze for almost two years. I dived into work and just tried to hide the pain by keeping busy. I never even took the time to clean out their closets and go through their stuff. Instead, I practically lived on the road. I was just a machine....I totally out produced everyone in my division and I was making big money. The checks were direct deposited into my checking account and I never spent very much of it. I just didn't feel like living life.

However one day, I woke up in a hotel room and I honestly didn't know where I was. For several years, there were so many rooms, so many nights and so much sadness behind those doors. Although being on the road kept me away from the loneliness and pain of living the memories of my family in our home, I realized it was time to change. I needed to clean out the house, sell it, buy a condo downtown and move on with my life. I was even beginning to be open to another relationship...certainly a sexual relationship because it had been over two years.

So I bought a great bachelor pad loft condo and a few weeks later, I told my boss that I needed to scale down my work and give up much of my territory. He knew I was going to crash and burn anyway and so he was supportive under one condition. He expected me to break in the person that was to be my replacement.

We both agreed who that person should be. Linda was the brightest and most talented new recruit on our team. We hired her as a student trainee when she was in college and by the time she graduated, she had a good grasp on our business. She started working full time but worked on her MBA in an evening and weekend program and by the time she was 25, she finished and was ready to take on the world.

I was always impressed with her but I always felt that she was pretty much a female version of your stereo-typical nerd. She wore baggy pants, shirts that looked like they belonged on a guy, and never wore make-up or had her hair styled. She was just your typical "plain Jane" type of a girl.

A few weeks later, she and I were sitting together on a plane to Chicago for a two week road trip to all of our client sites. The first night, we went out to dinner and just started with small talk. I never really knew her but I found her to be very charming and a great conversationalist.

I found out that she was engaged to a young lawyer and although they had been engaged for several years, they had never set a wedding date. I shared with her the story about my wife and daughter and she actually cried and said she was so sorry for me. I thanked her and told her that I was finally starting to feel alive again and starting to take steps to move on with my life, whatever that meant.

The next night, we went out again after work and she told me that she that she had just watched an Oprah show in the hotel room where a Dr. Phil type of guy was talking about people's sex lives, or lack of one.

She surprised me by asking if I had slept with anyone since my wife died and I told her that I hadn't...that my wife was my first and my last. I told her that it has been several years now and "I guess I'm just a born-again virgin".

She said, "I can relate to that" and I said "I thought you said you were engaged...do you mean you haven't had sex with your fiancé for a while"? She said "no, what I mean is the virgin part.....I'm still a virgin...technically at least". She went on to say that she never dated in high school or college because she was such a book worm and introvert. She finally met her fiancé when she was in grad school and just like my past, she just figured that since she had waited this long, she might as well wait to save it for the right person at the right moment and that "alignment of the stars had just not come up yet".

She said that her fiancé dated a girlfriend of hers in college and her girlfriend shared that he was really a bad fuck. Linda said that actually he really wasn't that interested in sex with her at all but since they had decided to wait until her wedding night to go all the way, lack of sex wasn't much of a deal in their relationship, at least for her fiancé.

Then she acted a little embarrassed and said she wanted to get my advice on something, but she was afraid I would think less of her if she gave me the details. By this time, we had got to know each other pretty well and so I said go ahead, you can trust me.

She said "OK, I want to tell you the real reason we haven't set a date for our wedding. It is me, not him. He wants to get married but I'm not sure he is the one because.......because....I can't say it damn it"!

I looked her in the eyes and said "Look, I was married and I had a daughter just like you....you can trust me and I will respect your privacy."

She said "OK, we haven't set a date because I know he won't be able to satisfy me sexually". I said "how do you know that?"

She said "well like I told you, my girlfriend told me that he was bad in bed. He was raised in a strict religious home and according to her; he thinks most things about sex are dirty and forbidden. She said that her girlfriend said he pretty much put on a condom, stuck it in her, pumped her a couple times, came and then went to sleep".

Then she looked down again and said, "I don't know if I can tell you the rest". I looked her in the eye with an understanding look and said, "just go on...."

She looked at me and then looked away and said, "You know that for years I have pretty much been a bookworm...well business and marketing isn't all that I have studied. I've taken the time to learn about my own sexuality. I've read books, watched instructional videos and lately, I have progressed to watching porn. I have a collection of toys. Yes, technically, I'm a virgin because I have never known a man in the biblical sense, but I have a very active sex life with my toys. Let's just say that I lost my virginity with them a long time ago, in every sense of the word if you know what I mean."

"I know my sexual needs and I know that this man will never fulfill them. I told him a while back that even though we are saving ourselves for our wedding night, we can still do some things sexually. He asked me what I was talking about and I told him that I would show him. I did oral sex with him just like I do with my toys and when it was over; he called me a slut and said he didn't ever want to do such a dirty thing again."

"That was 6 months ago and since then, he has shown little interest in any type of intimacy with me".

Then she looked me in the eye again and said, "I suppose you also think I'm a slut?"

I looked deep in her eyes and said "no Linda, you are just a normal young woman with sexual desires and wants.....in so many ways, you are so much like my wife......." She looked relieved....it was starting to be a very awkward moment and so we changed the subject and talked about work related stuff.

In a bit, I paid the bill and we got up and left. It was still pretty early and as we were in the cab driving back to the hotel, we passed a night club that looked pretty respectable. She said that she took dance classes in college and hadn't danced in public for a while. She asked if we could stop for a while and I said sure.

My wife and I loved to dance and although I'm not that good, I went out on the floor with her. I was really surprised at how good she was and also, how sensually she danced. She would occasionally lift her arms and spin around me. It was then that I noticed her tits for the first time. They were just the right size and her bra was showing a lot of cleavage. Every now and then there was a break in the action and the DJ would play a slow dance. She held me tight and put her head on my shoulder. I could smell her hair and feel her tits on my chest and I got very hard. I know she had to feel my erection but she didn't move back. She just purred a little and I swear I felt her rubbing herself against my hard on.

Finally, it was getting late and we had to go back to our rooms for the night. We got in the elevator and when her floor came, she reached over and kissed me on the cheek and said good night. I almost said something to her, but the door closed as she looked back at me.

I went to my room, got undressed and went to bed. As I started to doze off, I thought about how good it felt dancing with her, and how good her body felt against mine and I started to stroke my cock, thinking about how much I really liked this girl. She was everything my wife was for me. Maybe it was time for me to move on in some new ways.

The next morning, we met for breakfast and hit the streets. We had a great sales call with one of my largest dollar volume clients. Linda had done her homework. She knew their account well and was able to answer every question they had and I was pleasantly surprised when she suggested another product line for their upcoming sales year. They tentatively agreed to give her idea a try and she told them that she would get a detailed proposal to them by the first of next week.

By then, it was noon and our flight didn't leave until two the next afternoon. We had planned it that way so we could both spend some time and enjoy Chicago. We had a light lunch and as we were going back to the room, she said that she was in the mood for pampering and she was going to the spa in the hotel for a "girl's afternoon out". I smiled and told her to enjoy herself.....I told her how proud I was of her for doing such a great job this morning and we set a time to meet for dinner.

I went to the fitness center in the hotel and did my workout and finished at the pool with a good swim. I was starting to get back in shape again and I was feeling great and frankly, was proud of the way my body looked. People had told me that I looked years younger than my age. I ended up in the whirlpool and as I was enjoying the water from the jets, I started to think about Linda. I got really hard and I started to stroke myself under the water. In a minute, another guy joined me and I took my hands off myself quickly but I kept thinking about this lovely young woman that I was getting very close to and feeling things about that I hadn't felt for another woman in many years.

I still had several hours to kill before it was time to meet Linda for dinner and so I went back to the room and took a nap. I got up in a bit and suddenly I had an idea. I called Linda's room and she answered right before I thought the call was going into voice mail. She seemed glad to hear my voice.....I was glad to hear hers and I told her that I was going to make reservations for us at the Signature Room on the 95th floor of the Hancock Tower for dinner. She giggled and said I must have read her mind. She said that she had picked up a few "things" on Michigan Ave that afternoon and now she would have the chance to wear them before we went home.

I told her I would meet her at her room in an hour and she said that would be perfect.

I put on my dark suit with a white shirt and a bright tie that I picked up at Nordstrom's. On the way to her room, I got another idea. I made a side trip to the hotel lobby and picked up a dozen white roses in a glass vase.

When I met her at the door, I don't know who was more surprised. She was shocked that brought her the flowers but when I looked at her, I was absolutely stunned. She looked like Julia Roberts did in the movie "Pretty Woman" when Richard Gere met her in the hotel bar on their way to the opera. Her hair was up and she was wearing a silky red dress. It plunged in the front and for the first time, I saw her ample cleavage. I told her to turn around so I could see her better and as she did, I noticed that the skirt was slit pretty far up on the right side so it showed most of her thigh up to about 10 inches above her knees.

She looked stunning and frankly, very sexy. My mind was going wild as it occurred to me that this young woman was maturing and growing up in front of my eyes.

The rest of the evening was a blur. We took a cab to "Big John" and we got a window seat with the perfect south view of the city. We had a bottle of wine and the food and service was great. As it turned dark, the fireworks started at Navy Pier and we were just mesmerized. In fact for the first time that evening, I was looking at something besides Linda.

It was getting late and so I paid the bill and we made our way to the elevator and took a cab back to the hotel. Once at the hotel, we got in the elevator and when it opened at her floor, she stepped out and started to walk away but then she turned around and just as the doors were starting to close, she stuck her hand in the opening to stop the doors. She then grabbed me by the hand and pulled me out of the car and into the lobby. I was stunned but then shocked me even more as she put her arms around my back and leaned up and kissed me on the lips!

We ravished the taste of each other's lips for a moment and then we broke free and it was me that said "we shouldn't be doing this....you are engaged". She looked me in the eye and said that she had something to ask me.

Not knowing what to expect, she pulled me close and kissed me again and said, "you remember the other day when I said that I was technically a virgin and was saving it for the right person at the right place and time"? I nodded my head and she said, "If you don't mind, tonight is the night, and you are the one I want to do it with for the first time".

We kissed again. The way I kissed her let her know that I wanted her as much as she wanted me. We walked down the hall to her room and when we got inside, we put the do not disturb sign on the door and when it closed, we got back in the kiss. Our arms were wrapped around each other and I let my hands drop to her ass cheeks and started to massage them as she moaned. I felt her hands on my chest and she took off my jacket, my tie and I reached up and unzipped her dress and let it drop to the floor.

I stepped back and to my pleasant surprise, she had on a see through black push up bra and lacy see through black thong panties. I stood there in awe of her beauty as she unbuckled my belt and dropped my slacks. She quickly pulled down my briefs and she gasped when my hard cock popped out. She said that it was bigger than her fiancé and in fact, it was bigger than any of her toys.

I reached around and unclipped her bra and she took it off. It was my turn to gasp as her perfect tits sprang free. If I didn't know better, I would have guessed that they were surgically enhanced but when I put my hands on them, I could tell that they were 100% natural. My mind was going wild......she was as beautiful as my late wife. And at this moment, she didn't seem to be 20 years my junior. She looked and acted like a very mature and sensual woman.