Tits Have Benefits Ch. 04

Story Info
She goes to California and gets more than she expected!
6.7k words
4.8
56.2k
29

Part 4 of the 13 part series

Updated 10/16/2022
Created 04/10/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
hottchic
hottchic
259 Followers

Thank you for everybody's support for this story. Andrea gets an invite to visit Trish and Sandy in California and the story takes an unexpected turn, although I am guessing that some of you may have figured out what direction things might go. Please note that in the first few paragraphs there is a lot of plot development with no erotic scenes but fear not when the erotic scenes do cum, nothing is held back...

*

After transforming myself into a shemale and returning to claim the love of my life Jane, I was adjusting well to a life living with Jane's lesbian lovers, now also my lovers. I was just settling into my life with Jane, Jenny, Chris and Ann, when two things came together.

First there was an E-mail from Trish saying that she and Sandy really wanted to see me again and that Sandy really wanted me to fuck her and Trish wanted to watch. The second thing was that the person responsible for contracting me to write software, a divorced woman in her mid forties called Liz, really wanted to meet me in her office in California. This is when I started to come up with the idea of using a trip to California to kill 2 birds with one stone so to speak. The trouble was I did not want to leave Jane for a week when I had only been with her for a few days.

Liz's company of course would pay for the ticket to fly to meet her in California, but I told her that I would have to delay coming over for a week or so because I did not want to leave my girlfriend, Jane as our relationship was still very fresh and new. Then Liz surprised me by telling me that her company would be prepared to pay for Jane to fly over with me if I was prepared to fly over in the next 3 days. She said that I was already saving her a hotel booking because I said I would stay at my friend's house while I was in California. After consulting with Jane, I agreed to fly over.

"Jane," I said, "are you sure you are ok about spending time away from the family (meaning Jenny, Chris and Ann of course)."

Jane replied, "Look I told you already, I will miss them like hell, but I have left them before for periods like to visit my parents and stuff." She continued, "but right now I want to be with you all the time, as we are just getting to know each other in an intimate sense that is."

"Yeah," I said "I feel the same way, I don't want to be away from you for more than a few hours."

"And," Jane continued, "We have a lot of catching up to do after the way you cheated me by being such a close friend that I could tell anything to, and yet not letting me see your feminine side for 2 years."

"Actually," Jane said, "in one respect it will be harder for the girls not having you around the next few days than not having me around, for the same reason, they are just getting to know you and you bunk out on them, especially Jenny," Jane continued.

I raised my eyebrows, "You think?" I asked.

"Yeah I do," Jane replied, "I think she has fallen for you hard." Jane continued, "I mean she told you to put your dick in her ass, she never let any of us do that with a strapon, she loves a strapon in her pussy but never wanted it in her ass."

"Well," I said, "I am sure she would let you do it if you wanted to Jane, she absolutely adores you."

"Yeah," Jane replied, "I know she would if I asked, but in your case she asked you to do it." Jane continued, "initially she agreed to give you a chance because of her love for me, but it has gone much further than that, she is falling in love with you the way she fell in love with me.

For me, it was like I was in a dream world, I said, "You know, Jenny turns me on something incredible, and her protectiveness towards me, even the way she plays at dominating me, I am growing to love, somehow it makes me feel special." However hard this might be for the remnants of my male ego to accept I thought to myself. "I also believe I am falling in love with Jenny." I finished.

At this Jane threw her arms around me kissing me hard saying, "Oh honey, this is what I want more than anything, that the two people I love more than anything also love each other."

So that is how Jane and I ended up arriving at LA airport. After picking up our bags we found that Trish and Sandy were there to pick us up. Trish and Jane looked at each other oddly. Then Trish said, "WOW Jane, you and Andrea look like you could be sisters."

To which Jane replied, "Funny I was going to say the same thing Trish, that you and Andrea look like you could be sisters.

Trish thought for a moment, "Actually it's not surprising because when I advised Andrea on her surgeries I was influenced by what I thought would look good for me and Andrea thought a lot about you when she was making her selections."

Hearing this Sandy commented, "Well given that Andrea's looks are based on two beautiful girls it is not surprising that she turned out so beautiful herself."

Trish and Jane heartily agreed with Sandy, and I blushed a little saying, "Thank you Sandy it is so nice of you to say that."

"Just stating a fact," responded Sandy, "Why do you think I want to fuck Andrea so much?"

"Actually I am really looking forward to seeing you guys together," said Jane, "and I am also looking to getting down and dirty with you and Trish." Jane added, "Actually I have a lot to thank you for Sandy, for helping Andrea to become an excellent pussy eater."

"The pleasure was all mine," Sandy responded, giving me a lustful stare.

Soon we arrived at Trish and Sandy's mansion. Trish and Sandy had done very well for themselves making erotic videos which catered to the Lesbian and Transgender market. They had also started a website called althookup.com which catered to people with alternate lifestyles who wanted to get into a relationship or just wanted some short term fun. The growing success of the new website had allowed Trish and Sandy to move from a luxury apartment to the Beverly Hills mansion that they now occupied.

That afternoon I had my meeting with Liz, I had told Liz about my feminine transformation and she was cool with it. I had spoken to Liz several times on the phone with my new higher pitched voice so I was guessing that she would be somewhat prepared for seeing me in female form. Trish and Sandy were also kind enough to lend me their third car, a Mustang convertible. For the meeting I dressed business like, with a pencil skirt coming just above the knee, a silk blouse and smart black leather shoes with 3 inch heels. Sandy had bought me the clothes already knowing my size. She said to me, "I want you to give a good impression at your meeting."

Pulling up outside Liz's office complex I got out and took the elevator to the 6th floor. And after waiting for 10 minutes in reception I was ushered into Liz's office. It was a large plush room with a large desk and also a leather sofa. When Liz saw me, she did not recognize me for a second, and then looking astounded said, "Andrea?"

"Yes," I replied "it's me."

"WOW Andrea, you look incredible," she said, adding, "I have always considered myself straight but looking at you I might have to reconsider." "I must say that you look a hell of a lot better as Andrea than you did as Andy, and you seem to ooze sexuality."

Looking at the self assured woman in front of me I took in her presence once again. She had a classical beauty and despite her age (she was in her 40's), her skin tone was perfect and virtually unblemished. She had nice firm c cup breasts and long brown hair and very shapely legs and ass. Like myself she was dressed for business with a pencil skirt and a loose pink shirt, unbuttoned just enough to show some cleavage while leaving a lot to the imagination, and her 4 inch heels served to make her look taller than her 5' 10" stature. I also caught a whiff of an expensive channel perfume.

When I had last met Liz she was going through a difficult divorce, and looking a bit hassled, but now she looked much more relaxed which was also reflected in her calm and generous attitude. Liz came straight to business asking, "Well Andrea, how are you coming along with the new front end to our orglife.com website."

Orglife was a social networking site like Facebook, Myspace or Twitter, combined with personal organizer and e-mail management features like Outlook but in this case on the internet. I was working on a frontend application for this website which would allow users to work in a more user friendly environment than an internet browser and also the ability to work off-line.

"Well," I replied, "I have been sending you all that I have been working on as I have progressed, but I wanted to show you the latest stuff I have been working on in person."

I opened up my laptop and powered up. Once I had the application running, I started explaining it to Liz, "Well here is the latest environment, the menus are accessed from a vertical bar on the left hand side of the page." I continued, "As you can see you have direct access to all organizer and social networking functions in both on-line and off-line mode.

"This frontend is also compatible with all the most popular e-mail systems both on-line and off-line allowing you to compose and manage your e-mails, as well as allowing for e-mails to be automatically generated from personal organizer and social networking functions."

"But wait," I continued, "this application also has addins for accessing and displaying information from the user's Facebook, Myspace and Twitter accounts, again allowing for automatically generated information."

"Wow," said Liz, "looking at my latest prototype software, "I am impressed, so much so in fact that I want you to code this frontend as a Psynphone app." Psynphone was a new 5G intelligent phone plus organizer and mp4 player and was taking the mobile phone market by storm.

This was incredible news for me. I was due to receive a large lump sum payment for my work on the frontend for PC's plus a 1% loyalty on every bundled application plus now the new work for psynphone which was bound to take off big time.

We spent the next 2 hours talking about the new project and what it would entail after which Liz said, "Enough about shop, Andrea come here and sit on the sofa with me." I relaxed more even than I had before which was saying something given that Liz had a definite skill at putting people at their ease.

We talked for the next hour about what Liz had done in her personal life since her divorce and she also seemed very interested in my transformation, on several occasions repeating the point that I looked so damn hot as a woman. She also seemed very interested in hearing that I had elected to keep my genitals intact.

Finally we finished up with Liz inviting me to come over for a meal at her house that evening and asking me to bring Jane along. She said, "I am dying to meet the woman who was the inspiration for you changing your gender."

That evening I slipped into a cute black lace bra and panty set that I had bought at Victoria's Secret plus the expensive tight black minidress with the black patent leather boots with 4 inch heels.

Jane had not seen this outfit and when she saw it she said. "Wow Andrea, when you are dressed like that it just cries out fuck me." And at that, Jane who was naked, pulled out a strapon and put it on saying, "Jenny told me that you would miss her doing you with a strapon so I should give you your daily dose."

At that she told me to bend over and pushed straight into my ass, "oh fuck," I yelled.

Encouraged by my response Jane started to fuck me hard saying, "Oh this is so hot, fucking such a hot fuckable bitch like you." Jane was wearing a double ended dildo so she was effectively fucking herself as she fucked me and came twice because she was so turned on.

At that moment I said, "Jane I think I am going to cum."

To which Jane replied, "Not in your new dress and panties you're not." And quickly yet carefully removed my dress, panties and bra, but leaving my fuck me boots on. She pushed me on my back on the bed and mounted me cowgirl style grabbing my tits and saying, "Cum inside me, you hot fuckable bitch and after moving up and down on me 3 times I was coming really hard inside her.

Afterwards I put on my clothes and Jane got dressed in a black halter neck dress with a multi layer skirt and black patent leather strappy sandals also with 4 inch heels. "Oh God, Jane you look so fuckable," I said, "I would fuck you right now if we weren't running late and we hadn't just done it."

Jane grinned and said, "Yeah we are just like two bitches in heat aren't we."

We had the top of the Mustang down and Jane was driving fast our long locks of hair blowing in the wind like two hot movie stars. Jane's hand reached across to me pushing under the skirt of my tight black minidress and gripping my stiff erection. "So what is Liz like?" she enquired, "Is she hot?"

"Yes she is," I replied, "but don't go getting any ideas, she is my employer after all."

"She is your employer," Jane said naughtily, "but I can do what I like with her." "You say she is in her 40's, so that means she must have plenty of experience."

At that moment we arrived at Liz's house, we stepped out of the car and holding hands we walked to the door and rang the bell. Liz arrived at the door and let us in. Looking critically at Jane she said, "Well I can certainly see why Andrea was prepared to change her gender for you, you are one beautiful girl and like Andrea you ooze sexuality."

Jane looked straight into Liz's eyes appraising her and said, "Liz you are also one very beautiful woman, Andrea was certainly not wrong about you."

"Why thank you," replied Liz, "by the way the dinner is almost ready, do you want something to drink in the meantime." Jane opted for a dry martini and I asked for a Gin and Tonic.

We then sat around in Liz's large kitchen while she finished preparing the meal. She talked to us about her 2 beautiful girls, Tracy and Tina, 4 and 2 years old respectively, they were currently sleeping, and asked us about our relationship.

She was fascinated by the group 'family' we had and had a lot of questions about how we overcame the Jealousy. "It just doesn't seem to arise," said Jane, "because we are always very open and honest and inclusive with each other and none of us ever feels neglected because whenever any one of us gets intimate with an outsider all the others in the shared relationship are welcome to join in."

Then Jane thought for a moment, "actually that didn't used to be true, because I used to sleep with men sometimes and because we had a lesbian relationship I had to do it without other members." Jane continued, "but since they accepted Andrea into the relationship I have no need to stray because I get all the dick I could ever want." Jane said this looking at me with eyes filled with lust.

At that point dinner was ready and we went to her dining room to eat. The meal started with an appetizer of garlic mushrooms, followed by grilled tuna with baby potatoes and peas, and finally home prepared chocolate mousse. All this was served with a dry white wine. The food was really delicious and while we were eating Liz asked me about my friends Trish and Sandy.

I explained that they were doing very well for themselves in Los Angeles and I also told them how much Trish and Sandy had helped me with my operations and treatments and even training in feminine behavior. "Well they certainly did an excellent job and I think the world is a better place with you in it, as Andrea that is."

"Thank you," I replied, "I certainly believe that in this form I am more authentic to the true me."

After dinner we sat in Liz's lounge area with me sitting in a comfortable chair and Liz and Jane sitting on the sofa together. Then Jane started admiring Liz's clothes, she was wearing a pale blue chiffon dress that came to mid thigh and pale blue sandals, Jane admired Liz's hair and her skin tone. It was obvious that Jane was hot for Liz, when she was sexually attracted to a woman and thought that the woman maybe available Jane was very direct about it. Then came what I had been expecting, Jane saying, "You know you look so fuckable tonight Liz."

I was about to interject with some humorous comment about Jane liking to be controversial when Liz suddenly kissed Jane on the lips, and as she did this Jane put one hand to Liz's covered bust and pushed the other hand under Liz's skirt. If Liz's pussy wasn't already dripping wet it soon would be I thought to myself.

Soon Jane and Liz had removed each other's clothes and Jane was getting to work eating Liz out. And in a few minutes Liz was coming hard saying, "Fuck Jane you are good, I never had oral sex from a woman before but it is definitely to be recommended."

Then Liz said, "I want to eat your pussy Jane, but remember this is new to me."

"You will be ok." Jane responded. So Liz very slowly licked at Jane's pussy and after a while of licking Jane started to make slow mewing sounds. Encouraged by Jane's response Liz started to lick Jane more strongly inserting the tip of her tongue into Jane's pussy causing Jane to make more noise.

Jane, breathing hard said, "Now take my clit in between your lips and suck it." When Liz did this, Jane cried out, "Ahhh ahhh ahhh." Breathing raggedly Jane declared, "You're a natural Liz."

Now the two women got on the sofa in the 69 position and started going at it with each other. The sight of these two beautiful women so obviously turned on by each other was really making me hard, so much so that I had to pull out my 7 inch dick and was stroking it slowly as I watched to two women, I didn't want to cum too quickly, I wanted it to last. As I worked on my dick I closed my eyes for a moment feeling my nipple as I wanked myself.

Then suddenly I was aware of another hand pushing my hand away from my dick and taking my dick itself. I opened my eyes to see that Jane had my dick in her hand and was guiding it into Liz's pussy.

The feeling was exquisite as I slid into Liz filling her warm tight cunt. I looked into her eyes as she moved with me inside me and her look was pure bliss. "You are right," Liz said to Jane, "you haven't really lived until you have experienced having the dick of a beautiful girl inside you."

Liz continued, "Oh fuck it is so great to be filled with a dick again after having gone six months without it."

At this point I realized that I had been set up. Jane and Liz had planned what they would do this evening before hand. That was why Jane had been making secretive phone calls. I had given Liz Jane's telephone number so she could name her as a next of kin for me when she made my flight booking. The two women might have been planning this night between them since before I had flown out here as far as I knew.

Then Jane got Liz to get off me for a moment and lie back on the sofa. Then grabbing me by the dick she pulled me over to Liz and inserted my dick back into Liz so that I was laying on top of her. At this point Liz kissed me hard as we started to fuck. I was concentrating on kissing and fucking Liz and feeling up her tits as she felt up mine when suddenly I felt something cool being rubbed in my ass. As this happened Liz wrapped her legs around me making sure I could not move while Jane forcefully invaded my tight ass with her strapon dildo.

As Jane penetrated me my dick jumped violently inside Liz causing her to squeal in delight. "Oh yeah Jane, fuck Andrea harder." Liz demanded. And Jane was only too happy to oblige, fucking me in the ass with long hard strokes. The effect of this was to continually push me deep inside Liz rubbing her G spot and Liz was squirming about under me in delight. She had already cum three times and she was coming again.

"Fuck me," Liz cried out, "this is incredible, so incredibly hot and sexy."

hottchic
hottchic
259 Followers
12