Chapter 19: Confessions

Story by Nunpata
Illustrations by Mat

I awakened from a deep, restful sleep. Looking around the room, I started to panic. ‘Where am I?’ I thought. I don’t recognize this room. It seems familiar but, at the same time, it was foreign to me. I could smell coffee brewing and birds chirping. I turned to the only window in the room. I could see a building across the street that looked familiar. My mind started to clear. It was my school. This is my new bedroom. I am living in a house instead of an apartment. I have a roommate. A very beautiful and sexy roommate.

The last twenty-four hours had been a whirlwind of activity. It actually started three weeks ago when I received a letter from Ann. She asked me if I would be her roommate in a rental house in Colorado Springs. It was a dream come true for me. I was falling hard for this woman and wanted to be around her all of the time. I borrowed the foreman’s phone, called Ann in Iowa. I emphatically said, “Yes, I want to be your roommate.”

Twenty-four hours ago, I ended my summer job. I packed my gear and five hours later I pulled into the driveway of our new home. The front door was wide open. The only thing barring my entry was a screen door. I looked inside and standing with her back to me, I saw Ann for the first time in three months. I froze in place. My breath left me. All that Ann was wearing was a small black bra and an even smaller pair of black panties. The panties were so small that they didn’t even begin to cover her butt cheeks. My cock began to grow.

After seeing this, my big head said to knock first before entering. Give her time to cover-up before opening the door.

My little head said, ‘If she didn’t want someone to see her bare ass then she wouldn’t have worn those panties. Go inside and surprise her.’

My little head won. I stepped inside and said, “Honey, I’m home.”

Ann turned around and when she saw me, she ran to me and wrapped me up in her arms. With my arms trapped by her embrace, I did the only thing I could do. I put a hand on each naked butt cheek, squeezed, and pulled her into me. I love the feeling. So did my little head because his body grew into a complete erection. After a minute or so, I tried to back up but she just tightened her embrace and said, “Don’t you like to feel me close to you?”

“I love to feel you close to me,” I said. “And someone else likes it too.”

“I know,” Ann relied. “I could feel how much he likes being close to me.”

Ann and I finally broke apart and we toured the house. I told her about a few things I would like to do to the house and she promised to set up a meeting with them for today. I remember that she also said that we needed to do some shopping to do today. I took Ann out to an early dinner and afterward we went back to the house. For several hours we discussed finances, chores, and sharing. It really amazed me how we were both on the same wave link. We agreed on everything we discussed.

It was getting late when she said she was tired and we should go to bed. I was tired also, but not too tired to ask Ann, “Your bed or mine?” Wow, did she ever get defensive. She went to her bedroom, returned quickly, and gave me a piece of paper. It was a Relationship chart. She explained each type of relationship. After she got through with what a ‘good friend’ is, she stood up and held out her hand. I knew our discussion was over for the night. I was comfortable being her good friend for now so I didn’t ask her about the remaining levels of friendship that were listed on her chart. Instead, I took her hand and walked her to our bedrooms.

I was starting to feel real good after my mind adjusted to the new surroundings. I knew that I wouldn’t wake up tomorrow as disoriented as I was this morning.

I could still smell the fresh brewed coffee. I decided that I would join Ann in the kitchen. I also decided that I wouldn’t get dressed. I would only wear my skivvies. If Ann could walk around in her underwear, so could I. Before my feet hit the ground, I heard a knock at my door followed by the sound of it opening. Ann walked in carrying a tray with two cups of steaming coffee. I froze in place. Not because of what she was wearing, but what she wasn’t wearing. Ann was stark ass naked. She was totally nude.

When my mind caught up with what my eyes were seeing, I asked Ann if she had forgotten something. She looked down at the tray she was carrying and said, “No, I don’t think so. I have already added the sugar to your cup of coffee.”

“Ann, it is not the coffee I am referring to. I was referring to the fact that you are naked. Did you forget to put on underwear this morning or did I misunderstand you when you told me that we were ‘good friends’ last night? And the perk about being good friends was that we could see each other in our underwear.”

I watched Ann set the tray on top of my dresser, turn, and slowly walked towards me. Stopping only inches away from me, she bent at the waist and held my face in her hands. The look on her face was a combination of hesitation and anticipation; fear and acceptance; the look of a lover ready to make a commitment.

“Edward,” she said. “I didn’t forget to put on my underwear this morning. I chose not to. I wanted to show you my naked body. I wanted you to know that I felt we were more than ‘good friends.’ I wanted to let you know how comfortable I am when I am around you. I wanted you to know how much I trust you. I wanted to prove to you that we are, and always will be, more than good friends.”

I watched her remove my hands from her face and kneel before me. She took my hands into hers and said, “I had a lot of time to think last night. My mother and I had many mother/daughter conversations during my last week in Iowa before returning here. We talked about you and what type of relationship that I wanted to establish with you. Mom told me what she and my father had done when they were my age. She told me what they did before they got married, what they did after they married, and what they still do today.

“I remembered what my father said to me the day I left to come here. He told me that whatever decisions I make about what type of relationship I want with you that I should never tease you or keep you in the dark. ‘Men are clueless,’ he told me. ‘If you want something to happen, you have to tell them. If you don’t, you will risk losing them.’ I thanked Dad for his advice.

“But what you did yesterday is the real reason that I made the decision to come to you naked this morning. When you arrived here yesterday and saw me only in my bra and panties, you didn’t tell me to get dressed or to take off my underwear. What you did was to tell me how beautiful I am. When we came back from dinner and I did a striptease for you and told you that I wanted you to strip for me, you didn’t hesitate, you immediately started taking your clothes off. When you were down to just your underwear, you stopped.

“Edward, I am on my knees, naked, scared and vulnerable. I am asking, begging, you to be my first male close friend and the first penis to ever be in my vagina. Before you give me an answer, I have to tell you that I can’t give you my virginity. I am sure that you have already guessed that I have had many girls and women that were close friends of mine. And quite a few those became lovers. Some are still my lovers. I lost my hymen to my first female lover.”

Ann lowered her head and waited for my answer.

My big head told me to move ahead slowly. It told me that this woman was vulnerable and scared. She even shared with me that she wasn’t a virgin. That she had multiple female lovers. I will have to be truthful with her.

My little head told me to just drop my pants and show her my cock. That will answer her question.

Both of my heads won.

I stood up and with my right hand, tilted Ann’s face upward. “Ann, it would make me proud to be your first male ‘close friend.’ I would be honored to be the first cock in your pussy if you can accept that I can’t give you my virginity. I lost that to a 36-year-old, married woman when I was nineteen. And I lost whatever virginity that remained to her eighteen-year-old daughter a few minutes later.”

I removed my hand from under her chin, slid my skivvies down and let them drop to the floor. I told her that I was now as naked as she was. She lowered her eyes and looked at my naked cock. Looking back up at me, she gave me a thousand-watt smile, before grabbing my cock with both hands and guiding it into her mouth.

I immediately knew that this was the first time that she had a male member in her mouth. Her movements were jerky, her teeth scratched my sensitive skin and she gagged with only two inches of my cock in her mouth. She was so eager to have my cock in her mouth that I let her continue for a couple of minutes. Finally, my little head started complaining about the pain and I put my hands under her armpits and pulled her up and off my cock.

I reminded her that we had things to do this morning and if we didn’t get started soon, we wouldn’t get anything done. “You’re right. We need to go shopping and then meet the Hills.” She looked at the clock on the dresser and said it was too early to go to the mall but we could go to Target. “I’ll get dressed and be right back.” As she turned to leave my bedroom, I gave a quick swat to her bare bottom. She shook her bottom and ran to her room.

I knew I had time to change and would not have to hurry. It took her twenty minutes last night to get dressed to go out to eat. I decided to go commando. I put on the same casual pants I wore last night, slid my bare feet into a pair of loafers and was looking in the closet for a shirt to wear when Ann returned to my room.

“I’m ready, let’s go.” She was wearing the same jeans and sneakers that she wore to dinner last night. For a top, she wore a crop top. Her shoulders and midriff were bare.

I told her to hold her horses, I was still picking out a shirt to wear.

“I’ll never understand why a man takes so long to get dressed,” she said.

I just shook my head, picked out a shirt and we were on our way. I stopped at the local coffee shop before making our way to the Target store. In the men’s department we found a huge selection of underwear.

I asked Ann what she thought I needed to get. She replied, “You need to get a dozen loose fitting boxers, a dozen tight fitting boxers and at least a half dozen satin boxers.”

When I questioned her on the amount of boxers I needed, she said, “My mother told me that men are clueless. You need a dozen loose fitting boxers for when you are at work or outside, a dozen tight fitting boxers for when we are home or entertaining guests, and a half dozen silk boxers to wear when we are going out for the night.”

When I asked why I couldn’t just wear one style of boxers all the time, she said, “Clueless. You need loose fitting boxers so that your ‘package’ can breathe. You need silk boxers to keep your package in a state of arousal and your tight boxers to show off your package to others.”

I told her that I wouldn’t need tight boxers because I won’t be showing off ‘my package’ when we are entertaining guests at our house. “Clueless again,” Ann said. “The only people we will invite to our house will be good friends or close friends. Either way, they will know how we dress at home. The first time they visit they will be given the option to remain clothed or join us in how we dress. Think of it as a test. If they are not comfortable to be around us, wearing only their underwear, then they are not ‘good friends.’ Everyone who visits us at home for the first time will be tested.”

I had to agree with Ann that that was a very good way to find out what kind of friends they were willing to be.

We finished our shopping and on the way back to the car, Ann put an arm around my waist, and told me how much fun she had shopping with me. I told her that I felt the same way.

We sat in silence most of the way home. When Ann is quiet, she is usually thinking. I didn’t bother her even though I did see her sneaking peeks at me. We were almost home when I asked her if she was okay. She told me that she was fine. “I saw you sneaking peeks at me. Did I do something wrong?” She told me that I had done nothing wrong. She said that she was wanting to ask me a question but didn’t know if this was the right time to ask. I told her that she could ask me any question, any time that she wanted to and that I would always answer her truthfully.

That statement must have calmed some of her anxiety. She turned in her seat to face me and asked, “Edward, the next time we go out shopping, would you go commando?” I told Ann that if she was asking if I would go out in public with her without wearing any underwear, then the answer was yes. She said that I sounded pretty confident in my answer and I told her that I had a right to be confident. This morning when we were getting dressed to go shopping, I decided that I wouldn’t wear any skivvies. I have been commando all morning.

“No.”

“Yes.”

“Really?”

“Really!”

“Show me.”

I told that I couldn’t show her right now because I was driving, but I would show her when we got home. She fidgeted the rest of the way home. I had no more than pulled into our driveway then Ann was already getting out of the car. She came to my side, opened the door, and pulled me outside. I reached for the shopping bag and she told me to screw the bag, that she wanted me inside now. Ann closed the door as soon as we were inside and shouted ‘Show Me.’

I took off my golf shirt. “See, no undershirt.”

I took off my loafers. “No socks.”

I took off my pants. “No underwear.”

Ann looked at my naked body and started to smile. She looked at my face and stared into my eyes. “Edward,” she said. “I’m not wearing any underwear either.”

“No.”

“Yes.”

“Really?”

“Really!”

“Show me.”

Ann removed her crop top. “No bra.”

She slipped her sneakers off. “No socks.”

She took her jeans off. “No panties.”

I was looking at her completely naked body for the second time today. But this time there was something different about it. Her nipples. This morning they were like little buttons laying on top of her breasts. Now, they were sticking out a half inch from her breasts. They had tripled in size. Her pussy was different too. This morning her mound was flush with her body and her slit was narrow, hard to see. Now her pussy was flushed; it was plump, much bigger than this morning. Instead of a narrow slit, her outer lips were showing. Most of all, her pussy was sloppy wet. This morning she was showing me her body for the first time and she was nervous. Now, she was showing me what her body looks like when she is horny.

I held out my arms to her and she ran to me. She flung her arms around my neck. I put my hand on her butt cheeks and brought her pussy against my cock.

Ann whispered in my ear. “I love the feel of your penis touching my pussy.”

I whispered back, “It is not a penis, Honey. It is a cock searching for the entrance to your pussy.”

Ann hugged me even harder and started rubbing her pussy against my cock. “Fuck me,” she said. Put your cock inside my pussy and fuck me.”

I took my cock in hand and rubbed her pussy with it, trying to get her wetter and my cock more lubricated. As I lined up to enter her the phone rang. I tried to pull away, but Ann increased her grip on me and told me to forget the phone, she needed my cock right now. I told her the call might be important and she should answer it. The phone ringing destroyed our pent up passion and Ann agreed to answer the phone.

I could only hear Ann’s side of the conversation, but it went something like this:

“Hello.”

“Hi Jill.”

“Kind of.”

“You don’t have to be sorry.”

“Not yet.”

“I don’t know. It may be too soon,”

“Yes, I did. But not the first time.”

“I hadn’t thought of that.”

“Yeah, that might be fun too.”

“Maybe. I don’t know.”

“OK. I will.”

“Me too.”

“Okay, see you in ten.”

“Bye.”

Ann hung up and told me that that was our landlords. They invited us over to their house. They want to meet you. I told her that that was fine with me as long as we made time to discuss what we almost did before the phone call. Ann nodded her agreement.

I asked her how much time we had before we’d meet them. Ann told me that we had ten minutes to get changed and meet them. I didn’t think that was very much time, but when Ann said that our landlords were also our next-door neighbors, I felt that we could change and still get to their house on time. I wanted to make a good first impression and asked what I should wear. She said that I should dress in all black clothes including the black, tight boxers we bought this morning. She said I would look handsome and sexy in all black.

I told her okay and then asked, “Can we go to the mall when we are through with our meeting with the landlords?” She said that that was fine with her, but why do you want to go to the mall?

I told her, “While you were on the phone, I was thinking about what we almost did. The more I thought about it, the more I wanted to record it. I want to go to the mall and get a good movie camera and a tripod. I could set it up so it would record our first intimate moments.”

“I not only like your idea, I absolutely love it,” she said. “We should film all of our adventures. So, I agree to go to the mall with you if you agree to something for me.”

“Sure,” I said. “What do you want me to agree to?”

“I will continue to call you Edward in public, but when we are alone or with friends, I want to call you Eddie. Edward sounds way too formal for private times.”

I told her, “Deal,” and went to our rooms to change.

For the first time in our short roommate relationship, we finished dressing at the same time. Still in the alcove we stared at each other.

Ann broke the silence. “I knew you would look handsome in black and I was right.”

Ann had sandals on her bare feet. She wore the tightest pair of black yoga pants that I have ever seen. It was easy to see that there were no panty lines. For a top, she wore a sheer blouse which did almost nothing to hide her perfect breasts from view. Ann was going to our neighbors/landlords commando.

“There isn’t a man or a woman who could resist you dressed like that,” I said.

A big, beautiful smile from her told me that I had said the right thing. Hand and hand, we walked next door. During the walk, Ann said, “I want you to know that Jill and I are close friends, Very close friends. Her husband is kind and a gentleman. I trust him almost as much as I trust you and he has become a good friend. So, don’t be surprised at anything that happens in their house.” I didn’t know how to answer her so I just remained silent.

An older man was standing by the door as we approached. “Welcome to our house. Come on in.” The man looked to be in his late 40’s or early 50’s. He was tall, maybe 6’1’ or 6’2”, full head of brown hair graying on the sides. Decent build, no beer belly but not athletic either. I would guess his weight to be around 180 or 190.

Once inside, Ann said, “Tom, Jill, this is my roommate and close friend, Edward Moran. But you can call him Ed. Eddie, this is Tom and Jill Hill, our neighbors and our landlords.”

Tom was the first to speak. “I am glad to meet you Ed. Jill and I have heard a lot about you already and if you live up to half the things that Ann has told us, I think we could be good friends.” While I was shaking Tom’s hand, Jill stepped forward. “I agree with my husband. You have made quite a good impression on this young lady, and I am sure we will be good friends, even close friends.” I held out my hand and told her that I was glad to meet her. Instead of shaking hands, she moved forward and gave me a hug and a kiss on my cheek. Jill’s body was a carbon copy of Ann’s only older, maybe early 40’s, and she had brown hair and brown eyes.

Tom led Ann and me to a couch. As we sat down, Tom took a seat in a nearby chair, and Jill asked if anyone wanted something to drink. “Water? Iced tea? Soda?” Tom added that we could have something stronger if we wanted. I told Jill that an ice tea, two sugars would be nice. Ann said that she would like one also. Jill said, “Would sweet tea be ok? I told her that that would be fine, Ann agreed, and Tom asked for one also. Jill said, “Four sweet teas coming up.”

While Jill was in the kitchen, Tom told us that the house we were renting was originally built for Jill’s parents, Fred and Martha Haymer. They were in their 80’s and in poor health. “By having them next door, we could take care of them easier. Jill’s father passed away in March of this year. Fred and Martha were visiting with us at our house when he grabbed his chest and fell to the floor. The autopsy confirmed that he died of a massive heart attack. Martha took Fred’s death hard. She became more and more despondent. She quit eating and stayed in bed most of the time. It became evident that she no longer kept the house clean. Her own personal hygiene also suffered. Jill started taking care of her. She would make sure that her mother ate and kept her clean. As her mother’s despondency deepened, Jill began spending the nights with her. I tried to help Jill out by taking over for her in the mornings. I would fix Martha breakfast and sit with her while Jill got some rest. This continued for almost two months.

“It was a Saturday morning when I relieved Jill. I didn’t have to go to work, so I told Jill to go home, take a bath and get some rest. I fixed Martha breakfast and took it to her room. She was asleep, I called out her name to wake her up. Martha didn’t respond to my voice. I reached for her hand. It was cold and clammy. I could see that she was still breathing but wasn’t responsive. I called 911 and then called Jill. She didn’t answer. I called her again a few seconds later. Jill answered this time and I told her what was happening and that I had already called 911.

“By the time Jill got to the house, I could hear the wail of a siren. I left Jill with her mother and met the ambulance outside. I told the attendants what had happened and led them to Martha’s room. Jill stepped aside as the attendants went to work. We both heard one of the men say, ‘BP 60 over 40, pulse weak and thready.’ The other attendant had finished putting an oxygen mask over Martha’s nose and mouth. ‘We need to get her to the hospital fast.’

“Jill rode in the ambulance with her mom and one of the attendants. I followed behind. The siren was screaming, cars were moving aside. We were about halfway to the hospital when the siren went silent and the ambulance slowed down. I knew something bad had just happened.

“Jill was the first one out of the ambulance. She was crying.”

Jill came back to the living room carrying four large glasses on a tray. It looked heavy so I stood up and took the tray from her. Jill started passing out our teas. “Did I miss anything? It took longer than I had planned.”

Tom told his wife that he was just thanking us for renting the house. “I told Ann and Ed that we were very lucky to find such nice people to rent the house.”

“Do you like the house, Ed?” Jill asked.

“I do, Jill. I wasn’t too sure about the radiant heat, but I am sure that I will get used to it.”

“I am sure that you will. I love to run around the house barefoot and it is so nice to have a warm floor in the winter.”

Tom joined the conversation. “Ed, that’s not the only thing she likes bare when running around in the house.”

“Tom, how dare you say something like that to Ed? Ann knows what we do in the privacy of our home and if she wants Ed to know, she will tell him. I don’t want you to embarrass him before he gets to know us as good friends.”

“Jill, nothing that you or Tom could say or do would embarrass me. On the way over here, Ann told me that she considered you as a close friend, a very close friend. She also told me that she considered Tom as a very good friend who she hoped would become a close friend as soon as possible. What you may not know is that Ann and I discussed the role that friends, good friends, and close friends play. And the perks associated with each level of friendship. She has probably had those same type of discussions with you and Tom.”

Both Tom and Jill nodded their response.

“So, what I propose is that we drop the code words, decide we are all very close friends, and participate equally in the perks offered at that level of friendship. What do you think Ann?”

Ann didn’t waste a minute thinking. “Eddie, I agree wholeheartedly. Both you and Tom should know by now that Jill and I have already participated in the perks involved in being very close friends. And I told Eddie on the way over here that I would like to participate in those same perks with Tom. And if we weren’t interrupted by a phone call, Eddie and I would have already participated in those perks. But I do have one requirement. I want the first tab A that enters my slot B to be Eddie’s. Eddies tab A will be the first.

“For that to happen, Eddie and I will have to go to the photography store in the Mall and do some shopping. So, I propose that Tom and Jill discuss our proposal and let us know their decision tonight.”

Jill spoke next. “Ann, why do you want to go to the mall first?”

“If we hadn’t been interrupted by a phone call from a person who shall remain anonymous, Eddie and I would have already done the ‘dirty deed.’ I wouldn’t have had to add the requirement. After your phone call, Eddie and I decided that our first fuck should be memorialized. We decided to go to the mall and buy a movie camera and a tripod. We have never made a movie before and the camera will only show one view, but at least we will have something to look at years from now and remember our first time.”

Jill looked at Tom. It was the look that only long-time lovers could achieve. They were having a silent conversation. Each knew what the other was thinking. Each was seeking the other’s approval. Tom, almost imperceptibly, nodded his head. A huge smile crossed Jill’s face as she too nodded her head.

“Ann, what if I told you that you don’t have to go to the Mall? What if I told you that you don’t have to buy a camera and tripod? What if I told you that you could have your first time with Edward recorded from many different angles? And best of all, What if I told you that you wouldn’t have to send the film out to be developed by strangers?

Ann and I looked at each other. She said that might be fun and I told her that I liked the part about the films not being developed by strangers.

“Jill,” I said. “Ann and I agree that it might be fun. It definitely would save us a lot of money and I really liked the idea that a stranger would not be developing the film. But I am curious how we could be recorded from different angles. Wouldn’t that require a cameraman?”

“Yes, it would,” Tom said. “And I would be that cameraman. I will also do the developing, so no strangers will be involved.”

Jill said, “Tom, honey, I think we need to let Ann and Ed have some time to think about our offer. Playing around with each other is one thing. Fucking in front of a camera is quite another. Ann, Ed, we would still like to have the two of you come back here after dinner. Say around 7pm. I think the four of us still have some unfinished business.”

Ann and I agreed to be back to the Hill house at 7pm. I shook hands with Tom while the girls hugged. On the way back to our house, Ann asked me if I had any plans for this afternoon. I told her that I didn’t have any plans. “Good. We can get comfortable. I will fix you a snack and you can tell me more about yourself.”

“And what are you going to do if I don’t tell you more about myself?”

“You won’t be fitting tab A into slot B tonight.”

“In that case, I will tell you everything.” I hated to start our relationship with a lie but I had no choice.

The second we entered the house, there was a flurry of movement. Ann was stripping out of her clothes. It didn’t take long for her to be totally naked. As I removed my clothes, Ann was already in the kitchen making us a snack. I sat on the sectional, trying desperately to think about what I would tell her about my life. My cock was limp from worry.