As I was sitting there musing over the recent events I felt hands on my shoulders.
“What are you thinking?” Alan said as he turned me around to face him.
“I was just realising that my fears of being discovered are unfounded and also coming to the conclusion that I am really enjoying being Lisa. I am really thankful for the help that you, Rachel and Bob have given me in coming to this conclusion.” I said looking up at him from my chair.
“I’m glad about that,” he said. “We were worried that you would not be able to handle the situation today but we were convinced that you would not be discovered unless you wanted to be. Rachel was convinced after your first shopping trip that you could carry it off.”
“You mean she has told you all about our adventures?” I asked
“Yes and more.”
“Yes we have discussed you in quite great detail.” Alan replied. “Please don’t take this the wrong way but both Rachel and Bob have had a thing for each other for quite some time but Rachel is still in love with you. She did not want you to be upset about the two of them having an affair so when she discovered your secret she decided to try and use it.”
“Well Bob and I have been friends for a long time. We and I went to college together and he and I used to share a room. He found out about my dressing then and as Bob swings both ways he and I sometimes went out and a couple. When Rachel told Bob about your secret dressing he told her that he knew someone else who had a similar secret.”
“How did you feel about that?” I asked.
“To begin with I was not very pleased. Since we were at college we had an understanding that the whole matter would be our secret and we would not tell anyone unless we both agreed. Obviously this did not happen but in the end I think he did the right thing. Rachel was very good about it and, as far as I know, did not tell anyone including you.” he went on. “Once we had been out on that first trip to Haddon Hall when it was obvious that you enjoyed both looking good and acting as a woman, not to mention the sex, we decided that we needed to make sure that your confidence in your ability to both pass and act as a woman was increased.”
“I don’t see where this is leading.” I interjected.
“Just wait a moment and you will,” he said. “We decided that you lacked confidence so we set up this weekend to give you the confidence. This afternoon, I believe, has succeeded in doing that. Where we go from here depends on you. Bob and Rachel obviously want to go on with their affair and personally I want to continue in the way we have been doing. I really like you. In fact in some way I am vicariously living out my fantasies by being with you and going out with you. Eventually, of course, I would like to introduce you to Ann my female other half.”
“I must admit that I have really enjoyed myself so far this weekend,” I said. “I must admit that I enjoy the feeling of being dressed as I am and the effect it has had on the guests this afternoon. I am still not too sure how to handle the advances but I did feel flattered when they happened. I suppose if I admit it I am enjoying being Lisa more than I enjoy myself as Tom. All this is still a little new to me and the feelings may change over time but I think I want to continue being Lisa and Yes I would like to meet Ann at some time.”
“I’m really glad about that,” he said smiling at me. “Well the afternoon is almost over. As far as I understand it Bob has arranged that we are all going out on the town tonight. We have got some time before then so how would you like to meet Ann now?”
“You mean you’ve got your things here?” I asked.
“Well I told you about Bob and myself. Well I have a number of outfits here as I sometimes come and stay with Bob for the weekend,” he replied.
“Well if that’s the case then I would like to meet Ann. Do you want me to come with you while you change or what?” I enquired.
“If you don’t mind I would prefer to go and get ready by myself and then come back and introduce Ann to you. How about you continue with some of the work you have been doing? I know you have been enjoying it and I’ll see you when I’ve changed.”
“That sounds all right,” I replied and with that Alan turned and walked out of the room leaving me to my computer.
I was typing some more of the notes when Rachel came into the room and across to where I sat. She sat on the desk next to me and I was aware that she crossed her legs revealing quite a lot of thigh as she did so.
“What did Alan have to say to you?” she asked as I turned to look at her.
“He told me about him and Bob and about their relationship and about how you, he and Bob had worked at giving me confidence. He also said that he wanted me to meet Ann.”
“Did you come to any conclusions?” she asked crossing her legs the other way as she did so.
“I said that I was enjoying myself as Lisa and that I would like to continue doing things as we are at the moment,” I replied.
“How do you feel about me?” she asked, uncrossing her legs.
“I still feel the same, I think,” I said, “however I do realise that our relationship has changed and will continue to change but I still love you as I did on the day we got married.”
“I believe the change has gone a lot further than you think,” she said, once again crossing her legs, and leaning back a little. “If I had behaved as I have in the last five minutes, crossing and uncrossing my legs and revealing a lot of thigh, at one time you would have spent a lot of time looking at my legs but you have hardly looked at all. Have you had any sexual thoughts about me while I was doing it”
“Well I’ve noticed what you have been doing,” I answered, “but I can’t say that I have.”
“Women do notice how each other are acting,” she said, “and also how each other are dressed but they do not always react as a number of males react when they see a provocative display of leg. In a way you are now acting more as a woman than as a man. If you think about it you are dressed in much the same way as I am and probably show just as much thigh when you cross your legs. You probably don’t even think about it.”
“I must admit that I have not really thought about how I have been behaving at all times today.” I went on. “Most of the time I have just been trying to behave as I thought a woman would behave.”
“Of course you have.” Rachel said. “You have tried to behave as a woman does because that was the plan. You have succeeded well. So well in fact that you have been subjected to male advances. We need to sit down at some time in the future so that I can pass on some of the things I’ve learned about dissuading men from going too far when you don’t want to. I would not expect you to know too much about them as you have been coming from the other direction if you get my drift.”
“I understand what you mean,” I said. “I felt a certain amount of panic when David startled me when I was taking off my skirt. I knew that I couldn’t hit him but I was a little unsure of what I could do. Luckily I think I managed to handle it in an appropriate way.”
“So do I,” she said. “In fact Bob has just told me that all three of them wanted to know his secret of finding good looking secretaries like you. One of them even asked if he could hire you away from him. Bob said he laughed it off but he wouldn’t be surprised if the offer were made to you in the future. You obviously made an impression.”
“Thanks for the warning,” I said.
“How do you feel about the way your boss reacted to you this morning?” she then asked.
“I cannot believe that he did not recognise me,” I replied. “I must admit that I did hear some of what he said when he went into the meeting with you, Bob and Alan. I believe that all he saw in me was what he expected, a secretary with good legs. Do you know he tried to feel me up as he left?”
“He didn’t,” she said excitedly. “What did you do?”
“I said that he should keep his hands to himself and when he asked me for a date I said that I did not date clients as it put me in a difficult situation.”
“Good for you,” she said. “Perhaps I need to have a word with Bob about hiring you permanently.”
“You’re not serious!” I said
“Well good reliable help is often hard to find,” she said with a smile on her face as she eased herself from the table and made to leave the room, “perhaps you need to get on with your work now to keep in practice.”
I turned to look at her as she walked from the room. Was she really thinking that I could work as a secretary? How could I give up my job as Tom and work as Lisa? I must admit the idea did hold some appeal for me although I did not see how things could be worked out. I turned back to the computer and continued transcribing my notes.
This took quite some time and I had just stood up and was standing by the printer collecting the sheets I had transcribed when I heard a voice behind me.
“Excuse me miss,” a female voice said, “could you tell me where I can find Mister Andrews?”
“Sorry madam,” I began as I turned to look at the woman standing in the doorway and then it dawned on me it was Alan dressed as Ann. He looked terrific.
“Ann?” I asked questioningly as I walked across the room towards him.
“Yes I’m Ann,” he said. “What do you think?”
He was dressed in a dark blue skirt suit. Under the jacket he was wearing a pink camisole top and this colour was mirrored in the colour of his shoes. His wig, unlike that which I had seen in the painting of him as a bride was long blond and curly cascading down over his shoulders.
“I think you look terrific,” I said as I put out my hands and took his in mine. “I can’t believe the transformation. No wonder Bob and you get on so well. I now really appreciate you helping me to ‘come out’ and be myself.”
“In fact I think that you have really helped me come t terms with myself,” he said. “Since meeting you I have begun to think about myself and what I really believe in.”
We embraced. Neither as man and woman nor as two males would in a camaraderie fashion but as two females who are good friends and are meeting after some time.
“Well now what’s going on here?” Bob said as he suddenly appeared in the hallway. “My two sometimes women cuddling. How nice.”
“We are just hugging because we both feel good about ourselves as we are,” I said breaking off the hug with Ann. ”I need to thank you, Rachel and Ann or Alan for all the help you have given me over the recent days. It has really helped me to sort out an number of things in my mind. Exactly where I am going from now I know I will have help and support.”
“That’s really nice to know,” Bob said. “Alan and I came to an arrangement a long time ago. I don’t love him either as Alan or Ann but I do admire and enjoy sex with him as Ann but not as much as I do with your wife Rachel. I think you know this but Rachel still has some reservations.”
“I know she still says she loves me and I love her,” I replied, “but after recent events I understand that my feelings may have changed and I may be tending towards a different future. I think that the three of us, no four of us, need to sit down and talk abut how we feel and what we are going to do about the future.”
“I think we will but now we need to think about this evening. Ann am I taking three good looking women out or is Alan coming with us?” he asked turning to Ann.
“If you don’t mind I think Ann would prefer to come along this evening rather than Alan as long as that is all right with Lisa,” Ann replied.
“I’ve only just met Ann so it might be worth getting to know her,” I said, “so it’s all right by me.”
“That’s settled then,” Bob said. “Well ladies we will be leaving at seven for dining and dancing so if you’ll excuse me I’ll go and tell Rachel to begin getting ready. I know how long it takes you women to decide what to wear and then to get ready.”
The time was just before five o’clock and as I turned to look at Ann she said, “Let’s go and get ready together.” She held out her hand and led me across the hallway towards the stairs, our heels clicking on the marble flooring.
Once at the top of the stairs Ann said that we should go and shower and then meet in her room in half an hour. I made my way to my room where I slowly undressed, including removing my breast forms, while running a bath. I had decided as I left her that I would bathe instead of showering. I added bath oils and then lowered myself into the hot inviting water. I slowly relaxed and once my pores had opened and my skin relaxed I shaved my legs, body and arms.
I got out of the bath and towelled myself dry. I then covered myself in both scented powder and moisturiser, slipped into a pair of satin and lace panties. I then adhered my breast forms back onto my chest and put on a matching bra. To these I added a white garter belt and sheer white stockings. On top of this ensemble I put a sheer peignoir edged once again with lace. Placing my feet into a pair of white high-heeled shoes I then went to look for Ann.
The slowness of the movement was having a terrific effect on me. As well as my penis rising my legs began to shake and I found it difficult standing.
Soon , but not soon enough one of her hands reached the leg opening of my panties and began to ease out my erect member. She had quite a job but eventually she managed it. All the time I was beginning to shake uncontrollably. I almost sat down on her knees again but, by pressing down on her shoulders I managed to remain upright.
Keeping one hand making small circles on my inner thigh she opened her legs wider to make me open mine and putting one hand behind my buttock slowly pulled me towards her bending her head down as she did so and taking my member in her mouth.
She began making circles on the underside of the shaft with her tongue and slowly slid up and down the shaft.
By this time my hands were in her hair and my hips began to buck in time with her movements. I knew I was going to come in a very short space of time and said so.
She just kept up the movements of her hand on the inside of my thigh and her mouth on my member when suddenly her hand on my buttock slid from the cheek and into my anal crack. Her fingers went under the material of my panties and found the hole underneath and began to explore it.
I moaned out loud as this happened and involuntarily pushed away from her fingers driving my penis further into her mouth. My legs began to shake as her finger entered the sphincter and at the same time I came.
I don’t ever remember coming with such fury or feeling as I did then. Even with all the passion that Rachel and I used to build up I had never had an experience like that. I continued to pump into her mouth as she sucked as much of the fluid up as he could. My legs were still shaking so much that eventually I had to allow myself to sit down and rest.
When I did so she leaned forward and kissed me filling my mouth with my own sperm and fluid. I kissed her back with equal fervour and fully enjoyed the moment.
All through this she had continued to caress the inside of my thigh but now I was sitting down she was actually making small circles on the top and outside of my thigh.
I now wanted to give her as much pleasure as she had given me so I too began making circles along the top of her thigh and as I did so I eased myself backwards off her knees and allowed myself to slide down her shins until I was kneeling in front of her.
Slowly she opened her legs and allowed me to move in between them. I began kissing the inside of her thigh. First one side and then the other, gradually moving higher.
From where I was kneeling I could see that she was becoming aroused as her penis was beginning to strain against the front of her knickers. Reaching forward I gently eased it out through the leg of her French knickers, cradling it and fondling it in my hands. She leaned back a little and opened her legs a little more allowing me to approach closer.
I leaned in and began kissing the tip and used my tongue to make circles on the end. I opened my mouth and gradually eased the tip past my teeth and began to suck gently at the same time I moved my hands along the insides of her thighs brushing my fingernails against the tops of her stockings and the bare flesh.
Her hips began to buck and I had some trouble keeping her penis in my mouth but I began moving up and down on it pushing it as far back into my mouth as I could.
She began moaning and soon I could feel her tense up and knew she was about to come. I got ready for the ejaculation but as she came she pulled my head towards her and at the same time pushed upwards forcing her penis deep into the top of my throat and her sperm deep down it.
I began to gag. I could not breathe and managed to pull off her to be squirted in the face with semen. She leant down and kissed me and then she helped me up and we lay together on the bed.
“I’m sorry,” she said after a while, “but I just couldn’t help it. I had to be deep inside you when I came. I do understand that in the past when I have been Alan and we have had sex I have not been as violent but when I am Ann I seem to want a more fulfilling climax.”
“Don’t worry about it,” I replied. “I just felt that I could not breathe and also I felt I was going to be sick. That’s why I pulled of you. The climax I had was fantastic so don’t worry.”
We lay in each other’s arms for quite a while until we both realised that time was getting on and we needed to be dressed to go out with Bob. I needed another bath as did Ann so we hurriedly parted and began getting ready again.
I ran another bath and slipped in and once again luxuriated in the aromas of the oils I had used. I washed thoroughly, including making sure that my anal area was a s clean as could be. One thing which Rachel and I had not experimented with was anal sex and Alan using his finger was a little bit of a shock to me but something I was quite prepared to try again if I got the same sort of feeling as I had when I climaxed.
Once out of the bath I dried off and used liberal amounts of talcum powder and spray. I replaced my wig and went and say in front of the vanity mirror on the dressing table. I then carefully applied my make up, making it a little heavier than in the day as we were going out for the evening.
I replaced the bra and panties with another white lacy set and a matching garter belt. We were going out and I had decided that this time I was going to wear stockings and not tights. In reality I wanted to wear something provocative so that I would catch peoples attention rather than hide away from them. The experiences of this afternoon had taught me that I did pass as a woman and now I wanted to play the part.