Lily Comes to Life

Next thing I know I felt something warm and wet hit my anus where his thumb had been and then his digit worked its way into me millimeter by millimeter. I loved the feeling and I knew then that I would be having anal sex sooner than later! I was going to become a total ass slut!

When Josh's thumb was all of the way in my bum, I told him to start fucking me hard again. This time I moved back and forth forcing the action enjoying his rod pistoning into my hot wet pussy along with his thumb up my ass. It didn't take long for me to cum and I came hard yet again as my body quivered and my girl cum gushed from my pussy to our bed.

Josh...

Oh my god! Lily was exceeding my wildest expectations! She had, more or less, demanded me to shove my thumb in her ass while I fucked her doggystyle for the first time. After just a few minutes she had a really big orgasm as she screamed out in joy! I fucked my thumb in and out of her rosebud as I continued plowing away into her pussy. I wasn't really close again yet, having cum earlier, so I was hoping to get her to cum hard again before I did.

After a while, Lily cried out for me to give her more in her ass! I was sorely tempted to fuck her ass, but reminded myself to take baby steps because I wanted her to actually want to have anal sex often in the future. I didn't really have anything nearby that I could use, so I decided to work my other thumb into her back door next to the one already in her.

I pulled my thumb from her, bent over and spit a huge amount of saliva on her slightly gaping asshole. I spread my spit around her anus and then coated both thumbs in it. Next, I positioned my thumbs nail to nail and slowly pressed both thumbs in. "UUUNNNNGGGGHHHHH" Lily bellowed in a low-level growl as I sank my thumbs deeper and deeper.

"Are you okay?" I asked.

"OH MY GOD, JOSH! I LOVE THIS! PULL YOUR THUMBS APART AND STRETCH MY ASSHOLE WIDE!"

Fuck! This was beyond belief! I did as Lily asked and pulled my thumbs apart slightly, but it wasn't enough because she cried out 'MORE! MORE!' until I had her asshole stretched quite wide. She then demanded that I keep fucking her. I could actually see the outline of the head of my cock as it rubbed across the membrane separating her vagina and rectum.

It all became a little too much for me as I cried out, "I'M CUUUMMMMIIINNNGGGGGG!!!" and let loose a torrent of gism into the condom I had on my cock.

Apparently, Lily came hard the same time I did and released another torrent of girl cum onto our bed. I collapsed onto my left side as I pulled my thumbs from Lily's ass. We lay in bed with Lily's back spooned back into my chest as we both gasped for air after our exertions. After we had settled down, Lily turned over and kissed me hard for a few moments. When she broke the kiss, she smiled at me and said, "I love you so much and I love what we are doing. I just never knew sex could be so wonderful and fulfilling!"

The next thing she did really surprised me. She sidled down my body, then got to her knees as she pushed me onto my back and began pulling the condom off of my cock. When she had it off, she took me in her mouth and cleaned all of my gism off of me. When she determined I was clean, she sat up and with a big smile took the condom, tipped her head back and then poured the contents of the condom into her mouth. She even ran her tongue around a bit on the inside cleaning what little cum that was left out. Next, she smiled at me and said, "I love the taste of your cum!"

She fell back into my arms and kissed me again. I could taste my semen in her mouth, but I had no problem with that since she had taken the trouble to drink down what was in the condom. As we lay in each other's arms Lily looked at me and asked, "You don't think I'm too weird, do you? It's just I liked seeing that woman with the butt plug and I wondered what it would feel like to be touched back there. I touched myself a little yesterday and liked it, so I thought I'd go a little further today and found out that I really like my anus played with and touched. I was wondering where I could buy a butt plug of my own?"

I kissed Lily in a way that I hope expressed my love for her and then said, "Lily, honey, I don't think you are weird in the least. I am a bit surprised though. From what I understand, most women don't like anal play, so you are an oddity, I guess. But, I really like that you are an oddity because I'm an oddity too in many ways. As far as buying a butt plug is concerned, you can go online or go to one of the 'adult stores' in town. It may be best to go to a store so you can actually see what you're getting. I'll go with you if you want?"

Lily giggled and then said, "I think I'll ask your sister to go with me because I think I'd be embarrassed being with you. Is that okay?"

I smiled and said, "Yes, that's perfectly fine. Besides, my sister would probably be a better resource than I would be in one of those stores. She helps people with all sorts of sexual things."

"Can I ask one more thing?"

"Of course you can. You can ask a million more things and I'll answer to the best of my ability."

She smiled and then asked, "Can we forgo the gummy the next time we have sex? I want to make sure that I can enjoy it as much without the help of the gummy."

"Of course. I want you to enjoy sex in every way possible"

"Good, because tonight I want to ride you cowgirl style while we make love before we go to sleep!"

Lily...

Well, I have discovered I like having my anus touched, probed and stretched! During our afternoon video and sex session. I even had Josh stretch my asshole out while he fucked me doggystyle. I liked that so much that I came really close to telling him to fuck my ass because I thought I'd love that, but I didn't want to come off too slutty.

Later that day I called Josh's sister Jan and asked her if she was free during the coming week. She said she had a pretty full schedule during the course of the week, but she was available tomorrow on Sunday. We arranged to have brunch together downtown. She asked if everything was okay and I told her everything was great and that I needed her advice on a couple of things.

That night I rode Josh to a number of orgasms while we made love with me on top. I liked how Josh played with my titties and how I could rub my clit and get myself off. When we had finished I lay in my husbands arms feeling more loved than ever before and the happiest I had ever been!

The next day I met Jan at an upscale restaurant for lunch. This sort of place was out of Josh's and my price range, so I was pretty nervous about ordering something that cost too much. But Jan told me not to worry as lunch was on her. Apparently, her practice was doing really well. Before we ordered we made small talk as Jan asked how Josh was and how we needed to get together soon.

Finally, when our orders had been taken, Jan looked at me with her steely eyes and asked, "So, are you here to chew me out about the videos and gummies?"

I laughed and said, "No! As a matter of fact, I want to thank you for suggesting everything! This weekend has been the best of my life. I've learned a lot about love, life and myself, but I'm a bit worried that I may have gone a bit too far and may be freaking Josh out."

Jan laughed and said, "I don't think anything sexual can freak out my baby brother! I swear, from the moment he discovered his penis he did nothing but jack off!"

"Jack off?"

"Yeah, you know when men masturbate. That's one of the terms like wanking or pulling the pud."

I thought for a second and then put two and two together and began laughing. As I calmed down Jan smiled at me and asked what was so funny, so I said, "When we watched the first video, the first scene was of a woman masturbating. Josh said she was jilling off and I just got the whole Jack and Jill thing and found it funny."

Jan chuckled and said, "You know, I never really caught that. That is funny. Anyway, getting back to what we were talking about, what do you think may be freaking Josh out."

I lowered my voice and said, "Well, it's about anal sex."

Jan looked up as if in prayer for a moment and then said, "I'm sorry if he showed you something that offended you. I expressly told him to take things slowly and introduce you to self-gratification, then oral sex and then some different positions in which to have sex other than missionary."

"Oh no! Josh did nothing wrong, it's all me. You see, during one of the early videos I noticed the man touch the woman's anus which caused her to moan in pleasure. That little bit piqued my curiosity, so when I thought Josh wasn't looking and right after I had had an orgasm, I touched myself there and really liked it. And then yesterday, while we were watching a couple have sex doggystyle, I caught a flash of something red between the woman's ass cheeks and made Josh go back so I could see what it was. He told me it was a butt plug and that some people like having things in their bottoms and that they used them to prepare for anal sex.

"Well, I think I will like anal sex! As Josh fucked me doggystyle I made him put both thumbs in my ass and stretch me while he fucked me. I came so close to telling him to fuck my ass, but I didn't want him to think I was a horrible woman. So, am I a horrible woman?"

I could feel tears begin to well up in my eyes and almost immediately, Jan was by my side with an arm around me saying, "No, you are nothing of the kind! You are a loving, sensual woman who is discovering her own sexuality. Considering your upbringing, I must congratulate you for taking these steps to discover your sexuality. Anyway, if you like anal, then go for it. I love it myself."

Jan made me feel so much better and she remained sitting next to me as we ate. She told me things like many women had anal sex before vaginal so they could maintain their virginity and still have sex. I don't think I would ever had figured that one out. As we ate, we laughed as she told me stories about Josh as he grew up.

Finally, I asked, "Would you go shopping with me? I want to buy a butt plug."

A big grin spread across Jan's face, as she said, "I'd love to! Let's take my car!"

We drove to a little shop in a part of town I had never been to before. The shop was called 'Freya's House of Pleasure' and looked nice enough on the outside. Next door was tattoo/piercing parlor. As we walked in, Jan said, "A couple of famous porn stars are known to frequent this place. I know you don't know anything about porn yet, but keep your eye out for Missy Holloway. She will teach you more about being a woman and sex then anyone. The other works here frequently and is kno...oh wait, here she comes now."

A lovely Asian girl was walking up to us with a big smile and pulled Jan into a hug. When they pulled apart, the woman asked, "So, Jan, have you brought us another one of your clients?"

Jan smiled at me and said, "Well Elsie, this is my sister in law Lily, so she's not exactly a client. She is, however, just learning about her sexuality and is interested in butt plugs."

Elsie hugged me in welcome and then said, "You've come to the right place. We have the widest range of plugs in the country. So, why don't you follow me."

As we walked I was taking in all of the various inventory that was on display. I had no idea what most of it was for, but I was interested in learning. I noticed that Elsie was talking again, so I redirected my attention.

"Jan says you are learning about your sexuality. Can you enlighten me a bit?" So, I gave her a quick sketch of my sex life so far to which she kindly commented, "Oh, so very new." She then smiled and said, "You have a whole world of pleasure to explore and I'm sure you'll make the most of it with Jan in your corner.

"Okay, so here we are, the world of butt plugs!" Elsie went on to explain about all of the various types, sizes and materials involved and which ones were better for certain things. After consulting with both Jan and Elsie I bought a graduated size package that went from what seemed medium sized to really big. Jan explained that since I was beyond having nothing in me that I should start a little bigger. Next, she bought me a fat round plug made of glass that had little glass nodules on it for those nights I was home alone and was pining for Josh. That made me laugh.

Next, I was led to an aisle with hundreds of plastic penises! Before I could ask, Jan said, "These are dildos and can be a girls best friend. Now I want you to choose the one that most closely approximates Josh's size and don't worry about the color."

I looked over quite a few until I found one that looked just like him. I handed it to Jan who looked impressed as she commented that she didn't know her brother was so well endowed. Once she had that one in hand she grabbed another that seemed to be twice Josh's size and said, "Every woman wonders what sex would be like with someone who is really hung and you will too someday."

Next, I was led to one of the aisles we passed before. There were a lot of phallic shaped items of various sizes and when I looked at Jan she said, "Vibrators! A must for all women of discerning taste and refinement!" Both Elsie and I laughed. I ended up with three! One was a tiny thing that Elsie said was perfect for buzzing my clit while getting royally fucked. The next bigger one was about the size of a dildo which Jan said would complement the studded glass butt plug and the third was what was called a cordless 'magic wand'!

As we walked through an aisle dedicated to lubes of all sorts, Elsie pointed out the one that she thought was best, so Jan grabbed a 6-pack of 12-ounce bottles as she said, "You'll need all of this and more!"

I was shown BDSM equipment including whips, floggers, nipple clamps, restraints, electric devices and other paraphernalia for meting out pain. There were sounding rods which were used for probing the urethra, leather clothes, books and a couple of aisles worth of videos. Jan then walked over to the videos and asked, "Is there a Missy Holloway collection I can get for Lily? I think Missy is the perfect person for Lily to watch!"

Jan and I walked out of the shop with my wallet much lighter. As we headed back towards the restaurant and my car, Jan asked, "Are you in a big hurry to get home?" I told her I wasn't, so she replied, "Good, because I think we need to do a makeover on your attire. You are a sexual woman now and a beautiful one at that, so you should show off a bit more. I guarantee that Josh will love having you look sexier. Men love being seen with the hottest woman in the room and I think you would be the hottest woman in any room."

I blushed and said, "I really can't afford to buy anything else. The sex toys alone were too much."

"It will be my treat. I have more money than I know what to do with, so I'd like to do this for you and my baby brother."

I grudgingly agreed and then texted Josh to let him know that I wouldn't be home until around 6pm.

Josh...

I just got a text from Lily saying that she and my sister were going to be shopping for a while and to not expect her home until around 6pm. I texted her back and said, 'Okay, I'll order Chinese for dinner then and we can eat when you get home.'

Her reply was, 'That sounds good. After we eat I want a good thorough fucking! I love you!'

I had to laugh at her response. Last week I would have never even thought to imagine getting a response like that from her. She was like a whole different person, but still the sweet, beautiful girl I married.

My reply back was, 'We may not be able to eat our dinner because I may want to ravish you the moment you walk in the door!'

'Sounds like a plan to me!' was her reply.

Now, I wondered what kind of trouble my sister was getting my wife into.

Lily...

Jan pulled up to this cute little boutique and as we walked in she was greeted by name. Jan then introduced me to the store owner, a beautiful woman named Isobel. Jan told her that I was just discovering my sexuality after years of religious brainwashing and that I needed a wardrobe that brought out my natural beauty and sexuality. I couldn't help but blush as they spoke about me in those terms for everyone in the shop to hear.

Isobel looked me over and then said, "I'd guess a size 4 with a C cup?" I was about to reply that I didn't know my sizes, but it turned out her question was rhetorical as Isobel said, "Why don't you wait in the changing area while I gather some items for you to try on."

Jan grabbed my arm and led me to a changing area, pulled back a curtain on one of the rooms and said, "Why don't you get out of those things so you'll be ready to try on what Izzy brings you. When I had my dress off, Jan told me to lose my underwear as well. I looked at her kind of panic stricken so she said, "You have nothing to be embarrassed about, Lily. As a matter of fact, you should be proud to display your beauty to the world. So, why don't you start here with a first little step and then as you grow more comfortable we'll take bigger steps."

Jan's words calmed me, so I stripped naked and awaited Isobel with the curtain wide open, so that anyone who entered the changing area would be able to see me. When Isobel arrived with a rack full of dresses, blouses and pants, she looked at me and with a sharp intake of breath said, "My god, Lily! You are so lovely, I just hope these rags do you justice!"

I was guessing she said that to all of her customers, but it really made me feel good none the less. She handed me a very skimpy pair of panties and said, "By law you must wear panties while trying some things on, but most of these things would be best worn without undergarments."

I put on the panties and then I was handed a very sheer red blouse that was see through except for where my breasts were which had a small pockets which hid my nipples. I was then handed a pair of very tight blue jeans and a pair of sandals. Despite most of my breasts being exposed to view, I thought I looked really good. Jan was nodding her approval as well. Isobel then said, "You can wear this blouse a couple of ways. It can be worn buttoned up as you have it though you should leave the top three buttons undone." She undid the buttons for me and then turned me towards the mirror and I had to agree I looked sexier for some reason. "And, you can wear the blouse this way." She undid all of the buttons, pulled the back up a bit, pulled the two front corners up and tied them together under my breasts exposing my stomach. "You have a great tummy, so you should show it off."

Next, I tried on a series of sun dresses since we were in the early stages of summer. They were all very light and see through if you looked closely. Next came a couple of cocktail dresses for nights on the town and a little black dress for more formal occasions and business gatherings. Lastly, I tried on a number of teddies and nightwear that was designed for seduction.

As I tried these things on, a man happened to be in the changing area waiting for his wife or girlfriend. I decided to steel my resolve and not freak-out because a man was seeing me naked. With one of the items, Isobel told me I could take off the panties, so I stood in the changing area naked under a very sheer nightgown. If it was possible, the man looked even more nervous than I felt. Jan turned to him and asked him, "So, what do you think? Does the pink work for her?"

He stared at me unblinking and said, "I think any color would work for her."

Jan smiled and said, "I agree."

At that moment the man's partner came out of her changing cubicle and caught him staring at me. She looked me over and said, "My god, I just might become a lesbian! What do you think Charlie, do you think I'd look that good in that?"

Charlie turned his attention to his partner and said, "Yes, you would!" I had to agree because she was quite lovely.