A Date with Amy
Reluctance/nonconsent Story

A Date with Amy

by Jamtby 16 min read 4.2 (27,200 views)
gay nudity reluctance seduction non-con noncon
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Amy and I had been dating for a few months. She was divorced with two children. Her son Ted was 21 and finishing at the University of Pittsburgh. Her daughter Samantha was a sophomore at the University of Florida. Her former husband Henry had remarried a woman that he had a 4-year relationship before divorcing Amy.

At 46 Amy was attractive and professional. We met during an office Christmas party but didn't click at the time. She was going through the divorce and wasn't interested in any relationships. Maybe a one-night stand but nothing more. At that time, I had been divorced for over two years and hadn't really felt the need to start a new relationship. Paying for the failed marriage kept me focused on earning a living. I was not sure I could afford another. My sex life involved watching porn and masturbating. Not very fulfilling.

Over a year's time I did run into Amy in the company's cafeteria. We spoke and in fact she joined me and several co-workers for lunch. She worked in the Accounting Department and I was Vice President of Marketing. Both jobs kept us busy.

In mid-September I was extremely busy and finally decided on a late lunch.

Sitting by myself reading an article in one of the trade magazines we get at the office, a soft voice asked, "May I join you?"

It was Amy also having a late lunch. We had a pleasant conversation about work and company politics.

As we finished, I said, "Hey would you like to get a drink after work today? Woody's has a great happy hour."

For the first time in years I had "butterflies in my stomach" while asking Amy for a drink after work. It wasn't the food.

She smiled, "Yes, I would love to join you. Let's meet in the lobby about 5:30".

I replied, "That sounds great. See you then".

With another smile Amy headed off to the elevator for the 5th floor and I left for my office on the first floor. The next four hours passed very slowly. Although there were plenty of business issues to keep me busy, the time dragged.

At 5:30 I left several unfinished projects that I normally would have stayed and worked until they were completed but not tonight. I proceeded directly to the lobby. Amy had not arrived yet. The marble floors and wood paneled walls gave this area a feeling of grandeur. For the first time, since joining the company 5 years ago, I had taken time to appreciate this beautiful space. After a few minutes the elevator door opened, and 4 people walked out.

This striking brunette at 5 ft 8in, nice figure, and beautiful legs was the last to emerge from the elevator.

Amy immediately apologized, "I am sorry I am late, but my boss had to have some answers to a project he was presenting to the board tomorrow."

Smiling I said, "I understand that situation perfectly."

As a Vice President my car was parked in a covered space just a few yards from the main entrance. While the senior officers of the company parked in the garage under the building, I was still parking outside but with a covered place, it kept me dry during the rainy season. After holding the door for Amy, I hopped into the driver's seat. Within 5 minutes we were at Woody's. This was a local bar off the tourist maps. Unless you were from Tampa Bay you wouldn't find it. It had a great view of the Gulf of Mexico, good drinks, and great food.

With a glass of Merlot for Amy and Pinot Noir for me we started talking, at first it was the usual small talk about the office, her children, and Upcoming football season. After a while she started talking about her ex-husband. It soon became clear that this professional, attractive, and intelligent woman had deep anger about him. His job required him to travel throughout the country. A few years before their divorce, Henry was spending more and more time in Chicago. While there was always an explanation, Amy started to suspect something was going on in the "Windy City". Amy started tracking her husband's IPhone and found it was always at the same location when he was in Chicago. Confronting Henry, Amy wanted answers. The answer she got wasn't what she wanted.

Amy was in tears when she shared how Henry broke the news to her.

He reportedly said, "I am not in love with you. You are too inhibited, your boobs are too small, your ass is too big, and you are as much fun as a bag of potatoes in bed. I want a divorce and am leaving you."

Sobbing she said, "So, he left me, filed for divorce, and is living in Chicago with a blonde bimbo."

It was clear that this was a monumental emotional disaster. I would later learn how it completely changed Amy.

Our drinks turned into dinner, and cocktails. During our conversation I was surprised when Amy shared with me that she had been on several adult websites trying to meet new people. Over time meeting a variety of people she had expanded her life's experiences. I wasn't sure what that meant but clearly there was more about Amy that I did not know than I knew.

As we were getting back into my car, she asked, "Have you been on any adult websites?"

I mumbled, "Yes, some porn sites."

She then asked, "What types of sites do you like? Do you prefer heterosexual, Bi, gay, or transgender sites?"

I spoke softly and said, "Well I have been on a number but can't remember anyone that stands out."

Sensing my embarrassment Amy said, "I understand there are many exciting things to see. I have been on a number of sites myself. I can get excited on most but watch gay and lesbian porn is a real turn on for me. Have you ever been on my favorite website?"

I just nodded "No".

"You might want to check it out. I have a profile there. My screen name is 'FireyRose'."

As we pulled next to her parked car, she thanked me for a wonderful evening.

"Thank you for a great evening. I really enjoyed our time together and perhaps we can do this again. I really enjoy being with you."

As I held her car door, she gave me a big hug and kiss.

I said. "Good night, see you tomorrow at the office."

All the way home I thought about Amy's comments about adult sites. Once home, instead of heading for bed, I started my computer and went to her favorite website. After a few minutes I entered FireyRose into the Search menu and there she was. Amy's professional image was in marked contrast with her online profile. Listed as a bi-sexual, switch she enjoyed many things including bondage, whips, spanking, and anal play. Her pictures were in stark contrast to the image of her leaving the elevator. The black corset, bra, nylons, and heels made look extremely sexy. I started to develop a hard on just looking. After an hour of looking at her profile, I finally had to relieve my sexual tension by masturbating. Despite the temporary relieve, a good night's sleep was no longer an option. All I could think about was Amy.

Arriving at the office at 7:30 the next morning I was still in an aroused state. While a few projects required my attention, my lack of concentration made the work hard. At about 8:15 I received an inter-office email from the Accounting Department. The Senior Vice President of Accounting asked me to meet with his project manager over lunch at 12:30. Not certain what they wanted to talk about but being corporate savvy, I replied Certainly.

At 12:30 I was waiting at the cafeteria door and who should show up but Amy.

Smiling she said, "I see you received the email. I am the project manager you are to have lunch with." I smiled.

After getting lunch and finding a corner table away from the main area we started to talk.

She said, "I really enjoyed talking with you last night. You really are a great guy. By the way did you have a chance to check my profile?"

Not able to control my smile, "You are really a hot woman. I couldn't sleep all night just thinking about how great you looked. I am ashamed to admit I was excited."

"Don't be ashamed, I am flattered that you think of me that way. I sense you are like me in that you were brought up to think of sex as something dirty or only done in the bedroom. I was that way until I did some exploring and found new freedom. How about you?"

In a low voice I said, "My former wife became very dissatisfied with me. She felt I lacked passion and a willingness to make her sexually fulfilled. I was basically a useless drone rather than a bull male."

Gently touching my arm, "I understand. There is nothing to be ashamed of, you just need an opportunity to learn. I want you to come over to my house for dinner tonight so we can talk some more. I will make something simple and we can talk. In the mean time can you send me your projected sales figures and anticipated expense for the ARS project. That way my boss knows I was working, and he does want to see them. Here is my business card." On the back was her home address.

Smiling I said, "Yes for dinner and yes you have the ARS information by 3:00. When do you want me to come to dinner and what can I bring?"

"Great, just bring yourself. Dress casual and be comfortable. Let's get together about 7:00."

I replied, "Sounds good. I will see you then."

Back in my office I prepared the information for Accounting and sent it to Amy by 3:00. I received a reply, "Thank you for your help we appreciate it. We will not forget your efforts and they will be rewarded. "

The afternoon seemed to drag but at 5:45 I left the office. Running home, I changed into jeans and t-shirt. On the way to Amy's I picked up a bottle of good Merlot. The 20-minute drive took forever. Every traffic light was red, and traffic crawled. Finally, I reach her home in Westchase.

Amy greeted me at the front door wearing shorts, white top, and flip-flops. She gave me a hug and invited me in. The smell of Au gratin potatoes filled the house.

Amy said, "I hope you like green beans, Au gratins, salad, and steak. By the way would you grill the steaks for me?"

"Sure, I will be happy to but first let's open the wine and we can chat."

Pouring the wine, I handed Amy a glass and one for myself. Taking the steaks out on the lanai, where the gas grill was located, I started the grill and dinner was in progress. After dinner I helped clean up the kitchen and we moved to the family room.

Amy said, "Are you up for some interesting videos?"

I said, "Sure what are they about?"

The smile on her face, "these were not going to be g-rated."

The first video started out with a man and woman kissing and soon the woman's clothes were off. The male took control and tied her to the bed and sucked her nipples and pussy until she screamed with pleasure. The bulge in my pants got noticed but nothing was said. As the man fucked the woman Amy did not react but simply put her hand on my shoulder.

The second video started out with two women talking over a kitchen table but soon the older woman started to seduce the younger woman. As her clothes were slowly removed the younger woman became increasing aroused and screamed as the older woman sucked her pussy. As a dildo was inserted into the girl, she moaned and screamed in an erotic way. Amy could again see the bulge in my pants that betrayed my desire. She put her arm around me. I sensed she was getting excited.

The third video was of a man who what in a bar and became submissive of a gay master. The man standing naked with his erect cock looked helpless as the master forced him to turn around. At that point the master forced his slave to accept his cock anally. I almost exploded at that point. Amy again sensed my excitement and rubbed my arm.

Before showing me, the final video Amy turned to me and said, "This is personal. You can't tell anyone you have seen it."

She started this video and I quickly understood why. It was Amy standing in front of a man and a woman. After a few seconds. The woman ordered Amy to strip off all her clothes except her bra and panties. To this ordered she obeyed. The woman then ordered the man to inspect Amy and finish stripping her. At this point, Amy was becoming very aroused. Her flip-flops had long send gone and she pulled her top out of her shorts.

In the video the man slowly inspected Amy and removed her bra and panties. At that point I could feel her excitement and without a word she pulled her shorts off. Wearing only her panties and top I became more excited. Her beautiful legs and firm thighs became a fixation for me.

In the video the woman had come to Amy and started to kiss her mouth and suck her lips. The man inserted his fingers into her. At that point Amy could no longer control herself. She stripped off the rest of her clothes and sat next to me naked. Within a few seconds she was looking for my belt and unzipped my pants. Pulling my pants down, my erect cock betrayed my excitement. Without a word, Amy's soft mouth encircled my manhood and she sucked it. Within another minute or so I stripped off my clothes. Both naked we explored each other's bodies.

Then a low, moaning voice Amy pleaded, "Fuck me, please fuck me."

It had been almost 3 years since I had intercourse with a woman, but somethings don't require remedial training. Rolling Amy on her back and pulling her legs around me I entered her pussy. Each stroke seemed to arouse her more. Locked in a lover embrace I smelled her sweet fragrance and the softness of her being. Unable to control myself any more I released my cream into her body. She screamed at the release. Locked together for several more minutes, the soft whispers of thank you filled my ears.

As we separated, I noticed the video that had started this magical moment was still playing. In the video Amy was stretched across a table. The woman held her arms the man spread Amy's cheeks and inserted his cock into her ass. I was shocked.

Seeing the look on my face Amy said, "Have you ever fuck anyone in the Ass?"

I said, "No".

"Have you ever been fuck in the ass", was her next question. I said, "No, I am not gay and haven't ever been fucked that way."

Amy said, "You just proved you weren't gay, but still you should try it sometime. It would give you a new perspective. I used to be almost frigid, but things have changed thanks to some exploring of my feelings. How would you feel if you started a journey like that?"

Not certain how to reply, "I came from a very rigid up-bringing and haven't been very good with sex and women. Tonight, was great but I can't explain what happened."

Smiling, Amy said, "I want you to start a journey of self-exploration tonight. Let's go into my office right now and start."

Not certain what she meant I started to reach for my clothes.

"Stop, you don't need those just this minute. You need to stop worrying about wearing clothes and just be yourself." Grabbing my cock, she said, "Follow me and I will take you places you have never been."

Thinking to myself, "What happened the to accountant on the 5th floor? She is really different and very exciting."

On her desk was her computer. In a minute Amy typed in the website for a popular adult website.

Looking at me she said, "The first thing we have to do is get you on this website. Let's start by building you a profile. First, what name should we use. We want to keep your real identity off this site in case someone from work is cruising this site. How does William Reedy sound?"

I nodded, "I guess that's ok but is this really something I should be doing?"

Without hesitation she said, "Yes, you need to break away from the old. Based upon tonight you are ready to spread your wings. Now for a screen name how about "Readywilly456"?" Not waiting for my comment, "Yes that works." "Now how do you describe your orientation?"

"What do you mean?" I ask.

She replied, "How do you see yourself. Are you Master, Submissive, Slave, Gay, Switch?"

"I don't know?"

Amy said, "I am going to indicate you are a Switch. That means you can either be a dominant or a submissive based upon the situation. This orientation is often used when someone is unsure. It can be changed if you decide you are something else."

After completing the physical descriptions height, weight, etc. Amy said, "Time to write about your interests and desires. What do you want to say?"

I replied, "I haven't a clue how to write something."

"Okay, let me write something that should get some results and you tell me if this is okay."

Title Single WM looking to Explore

Profile: Single WM professional seeking to find my true sexual self after years or repressed feelings. I am 40 something, independent, and willing to learn. I am responsive to teachers and willing to try new things. Open minded, I am willing to do anything at least once. I have a good build and a medium cock which has proven to please. I love sexual roleplay and multiple partners. I am open to anything that does not involve illegal actions, kids, scat, or animals. My fantasy is being with people who enjoy being naked and uninhibited.

After reading the profile Amy wrote, I asked myself, is this really me?

Smiling Amy said, "It may be closer to you than you think. I didn't put gay curious which would have opened the doors to many new situations. But I will say you got excited when you watched the gay and lesbian videos so perhaps there's more than you realize."

I just shook my head.

Amy said, "I am going to post this and pay the first month's membership after that you are on your own. Who knows you may get contacted by "FireyRose"? She likes to meet new members."

With that she pushed the send button and Readywilly 456 was officially a member of this adult site.

Amy said, "I have enjoyed our time tonight. You are very good. Tomorrow night I have been invited to a party and would like you to go with me. You will meet some new people and we can have a good time together. Are you interested?"

I said, "Yes, I would love to go with you. What time?" She replied, "The party starts at 9:00. Please pick me up at 8:15."

I started to get my clothes, but Amy said, "You don't need your underwear, leave it with me. That way I know you are going home free. Besides, you may think of me along the way and must pull over to relieve the pressure. "

With this I got dressed. Amy gave me a big hug and kiss and I was on my way home.

To be continued.

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