tagTransgender & CrossdressersFrustration of Small Cock Pt. 06

Frustration of Small Cock Pt. 06

byjamtby©

As she stood there smiling at me I said, "You are one hell of a woman. I don't why those dumb men you knew in the past let you go but they were truly dumb asses."

She smiled. "Maybe they were just a warm up for the real man I am with today."

Part 6

After such an active afternoon it was time some wine and cheese. I said, "It must be 5 o'clock somewhere. Ready for some wine and cheese. I need to restore my energy after the time we just had. Merlot or Chardonnay?"

Ana smiled, "I am a bit hungry and a class of wine. I'm a red wine girl so Merlot sounds good to me."

"You open the wine and I cut up the cheese." A smiling Ana said.

Within a few minutes we were back on the lanai enjoying our wine. The sun had passed over courtyard and the shade felt good as we both relaxed.

"Ana, when I arrived at Guy's home I heard you called "Bitch Witch. I know when I first saw you I was filled with apprehension, but events proved me wrong. How did you get that reputation?"

The pause told me Ana had a story I wanted to hear. She seemed a bit uneasy thinking about how she was going to answer my question.

Slowly, she started to share more about her past. "You said that being naked was opening up and sharing who I am as a person. I have some things in my past that I am ashamed to admit. Unfortunately, over the past day I have come to really like you. I am afraid that you will be disappointed in me. I don't know."

At that moment it was clear there were some painful things in her past that Ana was ashamed to admit. Her words conveyed a fear of losing another relationship.

"Ana, in less than 24 hours you have become a very special person to me. A friend, and I hope your lover, supports their friend regardless of what might have happened. As far as I am concerned nothing that happened before last night at Guy's home matters. You have stolen my heart and filled my life with happiness in less than a day. I am with you regardless. Even if you rode through Time Square, naked on a mule, nothing matters. You are a very special woman and I am here to support you."

Almost sobbing she said, "I have come to really like you. In my life love has always disappointed me so I am not sure what that really is. But you are special to me. I will share some things from my past because I really want to be truly naked with you."

Shaking my head in approval I got out of my chair and stood in front of Ana. The kiss I put on her lips I would say, "It's okay I am with you."

Sitting back down I saw a slight relaxation in her face. I knew this was going to be hard for her but she needed to get it out.

"After the divorce Richard and I continued to work for the same company. We were cordial in the office but did not speak to one another after work. Richard rented an apartment with Jose. I needed a roommate to help with the expenses. I put a notice out on a social media bulletin board. Within a few hours I had received 5 responses. Three of those were men and I didn't need that. The fourth response was from a woman named Paula Grieg. Paula had just taken a position with our company. Like me she had been with Google and wanted out. Her start date was the following Monday. She needed a place in San Jose. We talked and got along well. The fact she was joining our company made the decision that much easier. She had already been vetted before hiring. I knew she could pay her share of the expenses and be a safe choice."

"Paula moved in on Saturday and started work on Monday in our office. Like Richard she was a software engineer. Her primary duties would keep her in the office most of the time. We started building a very positive relationship."

"Besides having worked at Google we shared another common interest. We both like to go sailing. I had joined the American Sailing Association and taken their basic course while a Google. Paula was very experienced. She owned a 30 ft Hunter sloop and a slip at San Leandro Marina. She was born in Michigan into a sailing family. Her father won many races on the Great Lakes. During the summer they practically lived on their 40 ft Tartan."

"After a month or so of settling into the apartment and work, Paula asked me if I wanted to go sailing. I jumped at the chance. The next Saturday we headed up to her boat. The weather was perfect and nice breeze and warm temperatures. Moored neatly in slip 372 was her boat, 'It's Time For Fun'"

"Paula apologized for the boat being so dirty. It had been over 6 weeks since she had been on it."

"Responded that's not a problem let's get some water, soap, and scrub brushes and clean her up."

"Within a few minutes a fresh water hose was connected to the pier and the cleaning began. If you hang around sailors very long you quickly learn half the fun of sailing is keeping your boat in beautiful condition. Within an hour the 'Time For Fun" had returned to her rightful place as a good liking sloop."

"We stopped by the marina store and pick-up some sandwiches, a bottle of wine and a 24 pack of bottled water. Ready to sail, Paula had me handle the mooring lines while she backed the boat into the channel. The expert way she handled the boat was impressive. We were on our way. Once clear of the marina and out into the middle of San Francisco bay, the quiet and peace overcame me. Just the wind in the sails and the water rushing past the haul were the only sounds. A few sea birds passed by, but we were alone."

Paula said, "Have you ever sailed topless?"

I said, "No, is that legal?"

She smiled, "Absolutely." Wearing a two-piece suit she pulled off her top.

"Ana, go ahead and take yours off. You will be amazed how good you will feel."

"I had a one piece suit on. Taking down the top would be ok by a bit awkward."

As I hesitated, Paula encouraged me. "Take that damn suit off and feel the breeze on your body. It is amazing trust me. Unless you have some strange body parts I have seen everything there is to see when women are naked."

With further hesitation Paula pulled off the bottom of her suit. "Just be sure to leave on your deck shoes. I don't want you slipping off the boat and have to explain to the Coast Guard how you were naked in the bay."

"I chuckled at that joke and took off my suit. Paula was right. It is amazing being naked with the wind blowing across your body and the warm sun gently kissing your skin."

"Want to sheer? I will work the sails and you man the helm." With that I moved to the back of the cockpit and took the helm from Paula. In that exchange as Paula moved forward she brushed my breasts. For a brief instance I had an erotic rush. I had hoped she did not notice it."

Sailing for two hours the time was amazing. Paula' expertise in manning the sails made the time almost effortless. At some point Paula said, "I ready for lunch and some wine. There is a small island about 2,000 yards from here. Let's head over there and drop the anchor. Just in case there are other boats there you will have to put your suit back on "Lady Godiva""

We both laughed and soon I was back in my suit and we are ready to anchor. At that point Paula took over the helm and I manned the anchor. When Paula gave the order the anchor I dropped it over the bow. Once she was certain we were anchored Paula said, "Time for lunch. Let's eat."

With our sandwiches and glass of wine this seemed perfect. Since there no other boats were around Paula pulled off the top of her suit. "Go ahead Ana take your off and enjoy the breeze and sun. Besides no tan lines this way."

At first, I didn't want to do it. Then I did so down my top came to the waist. Awkward by that was ok.

In a moment Paula moved closer and again brushed my breasts. It was clear that I was reacting to her touch. Within a minute Paula's hands were all over my breasts and I became erotically excited. At first, I said, "Paula stop." She didn't and within another minute her lips were on mine. I didn't resist but passively let her kiss me. I was become very excited.

Paula whispered, "Let get that suit off so you can really relax." With that she gently lifted me high enough, so my body was free on the seat. "Go ahead and get it off Ana do it for me."

I obeyed and within a minute I was naked and being lead down to forward berth. Paula pulled me onto the bed and began caressing me. I melted like butter as she kissed and massaged my body.

"You haven't done this before have you?" Without saying a word, she continued, "I can tell but just relax and let me take you where you really want to go."

Her hands reached my vagina and slowly started rubbing me. The tension built until I could no longer take it. I screamed, "Oh god this feels wonderful. Please don't stop." Within a minute I had a massive orgasm". Exhausted I laid in her arms as she continued to stroke me.

"Now that wasn't so bad. You found a true release and peace that comes from a close friend who understands your body."

After an hour or so Paula said, "We need to get back before it gets dark and the tide makes it more difficult to get back to the marina."

With Paula at the helm I pulled the anchor and we were off. It took another 1 ½ hours to return to the marina. Once we moored the boat, like good sailors we washed down the 'Time For Fun'.

With the work done Paula suggested we get a glass of wine at one of her favorite sea side bars. I agreed and with a 5-minute walk were arrived at a place named "Fat Fannies"

I asked what kind of place is this? Paula smiled. "It is a friendly place where people meet and share a drink and share sailing stories."

The modern look and cheerful atmosphere seemed inviting enough. Inside the crowd was friendly and music great. Since Paula had taken me out on her boat, I bought the wine and we found a table towards the back of the bar. It was at that point I realized that the only man in the bar was the bar tender. The rest were women.

"Paula, is this a bar for lesbians and gays?"

She simply smiled and said, "It is a place where friends meet regardless of their orientation."

My next question was more direct. "Are you a lesbian? What happened on the boat was that a moment of passion or something else?"

Paula shook her head, "No, I am not a lesbian and neither are you. We had an experience together that hurt no one and no one will ever know about this afternoon unless you want to tell them."

"Paula, I think you are a terrific person and really fun to be with. I have had too many bad relationships and don't want to spoil ours because I am not interested in women."

"Ana, that is not a problem either because I am not really interested in a relationship with women either. When I brushed your breasts earlier in the day I sensed you became excited. That somehow aroused me. It was a spontaneous, impulsive reaction. I am sorry."

"I understand, and you don't have to apologize."

At that moment Paula's demeaner changed. Entering the bar was a big, heavy set woman wearing leather and chains. Her hair was cut short. She looked like the stereotypical, Hollywood image of a Dyke. The first words out of Paula's mouth were, "Oh shit. Let get out of here through the back door."

Without asking why we got up and moved quietly to the exit at the back of the bar. Just then we heard the woman shout, "Paula I haven't seen you in a long time. Where have you been. Come up here and say hello to Donna."

Paula froze. I asked in a low voice, "Who is that person?"

The response was short, "She's the bitch of San Leandro."

In a firm voice the bitch said, "Paula come here I want to see you and bring your friend."

At that moment Paula changed into some sort of obedient person. "Yes, Donna, it's good to see you after all these months.

Donna waited for us to come to her. Paula gave her a Luke warm hug.

"Paula you and friend come with me." With that Paula whispered, "Please come with me. This won't take long."

Donna set a fast pace as we walked the 5 blocks to her place. There wasn't any conversation just following her. Upon reaching her place she opened the door and we were escorted in.

"Paula, you know what I expect."

She responded, "Yes Mistress." At that point Paula stripped, neatly folded her swimming suit, coverup and placed her shoes on top. She then assumed a kneeling position on a carpet square.

Donna looked at me. "What are you doing with Paula? I want to know."

In a firm and defiant, voice I said, "She is my roommate and we were sailing together today."

Her response was, "That's nice. I am her Mistress and own her. I will be your Mistress and own you do you understand?"

I said, "No I am no one's submissive. I am leaving. Paula, come with me."

Paula remained frozen in her place. That's when Donna ordered me to take off my cloths. I refused and started to move towards the door. At that point a strong arm grabbed me.

"Listen bitch. You can obey me, or you can suffer my wrath, but you will do what I want. Now take those damned cloths off or I will rip them off."

I refused and that was a mistake. Grabbing both arms Donna ordered Paula, "Get over here now and strip this bitch while I hold her and make it fast. Paula jumped up and said yes Mistress." In less than a minute I was naked and being held firmly by this Dyke.

I was pulled over to a wooden chair. Forced to sit in it and was tied to it. At that point Paula was ordered back to her place.

Donna began to examine me closely. When she started to rub my breasts, me reflect erotic reaction took hold. Donna smiled, "So you are one of those few women who are aroused by simply touching your breasts." With a smile she continues to massage them and play with my nipples. I became aroused and the tension built until I started to moan. As she continued to arouse me I could not stop. At some point I had a spontaneous orgasm.

"Now that is something. A sub that can orgasm without my using a dildo or electric shock. Paula, don't you wish you could do that?

Cowardly shaking her head in the affirmative, Paula's head down hoping she would not be used.

Donna continued her examination and saw my pubic hair. "Sub's don't disrespect their Mistress by covering their pussy with hair."

At that point my arms were untied, and I was pulled from the chair and lead to a table like ones used by massage therapists. Donna's strength easily pulled me onto the table. My hands and legs were strapped to the table with my legs spread open.

"Paula, get over here. You are going to shave your roommate and make her presentable to me."

Obeying, Paula got up. Went to a cupboard pulled out a razor and shaving cream. A pan of hot water and a hot wash cloth completed the materials she would use. First the hot wash cloth place on my pubic region for a few minutes. It was so hot it hurt. Then the shaving cream and finally the razor.

As Paula started to shave me Donna spoke. "Nothing like watching a sub shave another sub. I get excited watching you."

The rest of the night Paula and I were under Donna's control and supervision. This was only the first of many sessions we endured as we became more drawn into Donna's world and BDSM.

I had to interrupt. "Ana, why did you continue to meet with Donna and become more involved? Did you find something that fulfilled your passion or what was it?"

Ana tried to explain but had trouble giving me an answer. I broke the silence by saying, "Ana, what you did has no bearing on how I feel about you. We are here today that was in the past."

Softly at first Ana said, "I don't know why Paula and I could not free ourselves from the "Bitch f of San Leandro". The question I asked myself over and over was 'how could two educated and intelligent women submit to such humiliation and degrading activities? I didn't have an answer. We were under her influence and must have liked it. I will say that during that three-month period all I thought about was out next visit with Donna."

"You asked me how I became the Bitch Witch at Guy's parties. It happened while Paula and I were with Donna."

"About three months after meeting Donna, Paula and I were back at her place. As usual we stripped and assumed our positions on the floor. That night I was ordered to come with her to another room. She wanted to talk with me."

I said, "Yes Mistress what is it you wish of me?"

Donna looked me straight in the eye. "You are not a true submissive you are a dominant. I have done my best to break you, but you will not be broken. You obey my commands but show the traits of a dominant. I am going to make you a dominant and teach you how to control people through BDSM."

She continued, "Many men and women have a desire to humiliated and forced to submit sexually to a dominant. Genders are the same in this regard. A man is as likely as a woman to crave submission. It is liberating for them. They get gratification by obeying someone who controls their sexual responses. The more you control and provide pain and humiliation the greater their satisfaction. It may sound strange, but it is true. You can satisfy those individuals"

"Ana, you have two weaknesses. The first is that your breasts are so sensitive that you become very compliant almost immediately when they are touches them. The second is a deeper issue. You have a very big heart and want all the people you meet to feel good. That is who you are. If you believe that you are helping people through BDSM, you will succeed in making them happy in ways you have experienced. I am called a bitch and perhaps I am, but I also recognize the needs of people. You do as well."

Donna continued, "Tonight I am going to start training you as a dominant. Paula is a wonderful woman who enjoys being a submissive. You will work with her to learn skills and please her at the same time. As she cries and curses you, know that she loves every minute and will want more."

Ana then looked at me and said, "Honey you asked how I became the Bitch Witch. I spent another 6 months learning from Donna. I wanted to help Guy's girls and not abuse them. I wanted to make them happy. I must admit I didn't always enjoy that role, but it did give me some purpose. That was the path I was on until that damn bra protecting my breasts broke and you changed me. I hope you understand and do not think I am an evil person."

Looking into her wet eyes. "Ana, you have my respect for sharing that with me. I understood early in our relationship you had set some barriers to protect yourself from further hurt. You have had some bad experiences with men. I also saw something you could not hide, even though you tried. That was you soft heart and inter beauty. I suppose that sounds like just words, but they come from my heart."

Ana softly asked, "Will you hold me and not let me go? I am not perfect, but I need someone who can love me regardless of what I have done or mistakes I might make in the future."

Pulling Ana out of her chair I gently guided her back into the bedroom. Pulled a blanket around her and held her.

To be continued

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by Anonymous

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by UltimateHomeBody01/29/19

Really enjoyable story

Please get new chapters proof read.
Message me if I can help.

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by Anonymous01/20/19

My 2 cents

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by Anonymous01/19/19

Lust to Love

This chapter does a great job of illustrating how two people can bond regardless of their gender.. The roles of submissive and dominant support the needs for love and recognition of their individual needsmore...

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