My wife, Hailey, had never been close with any of her family. She officially moved out of her parents' house the day she turned 18 but had been living with older friends for over two years before that. We met towards the end of both our college careers, dated for two years and married during our third year together. We had just celebrated her 26th birthday (I was 27) and both were shocked when we got a call from her younger sister, Anna (then 17). It was the first time in over four years that any of her family had contacted us.
During this phone call I stayed nearby trying to figure out what was being said on the other side. In my mind I was thinking something bad had happened to her parents and her sister was delivering the news. My wife gave me no hints; however, after a few minutes I relaxed when she started smiling and laughing. Assuming the sisters were finally making up for lost time I left the room to give my wife privacy. Nearly an hour later she walked into the living room where I was watching tv to fill me in and deliver another shock.
Her sister, Anna, was fed up with their overly strict parents as well and wanted to come stay with us during her summer school break. Her parents had agreed to this only because they had planned a summer cruise and liked the idea of being alone together for it. My wife told me the decision was up to me since she works a traditional job and I work from home and would be 'baby sitting' most of the day. I could see she was excited about this so agreed it was fine.
A few days later we were at the airport picking Anna up. When we saw her I was taken aback a bit. The last time I saw her she was 12, awkward, skinny, all knees and elbows. But now, she was turning into a very beautiful young woman. She stood about 5'6", slender, long legs, flat stomach, 32b breasts, medium length brown hair with slight curls in it, and already had the start of a good summer tan. I had no sexual interest in her at that time. I was merely looking at her as a brother-in-law.
We all greeted one another with awkward hugs and continued on to collect Anna's bags. Once at our house my wife showed Anna around and helped her get settled while I went out back for a quick swim in the pool. The girls came out as my wife was continuing on giving the grand tour.
They both stuck their feet in to cool off. I swam up between my wife's legs, planted my hands on either side of her and pushed myself up out of the water to kiss her. Out of the corner of my eye I thought I saw Anna shoot us a look of hate, but when I turned towards her she was staring off into the water. I dismissed it and grabbed my wife's hands pretending I was going to drag her in. She giggled, and threatened to harm my sensitive areas if I did pull her in.
During our playful exchange Anna abruptly stood up and walked off into the house. My wife and I traded looks and shrugged, then used the alone time for a bit of light petting. She wrapped her legs around me, pulling me towards her, and ran her hands over my wet hair while I gently fondled her breast. She playfully slapped my hand away telling me to behave and that she would fuck my brains out later that night. She pushed me slightly away from the edge of pool and rubbed her foot against my trunks and over my stiffening cock. Just then Anna returned, now wearing a girlish pink bikini and her hair pulled back in a pony tail.
My wife stood up saying, "well, I guess I'll go change as well. Babe, will you go make us some drinks?"
"Um... I could... But..." I moved my eyes downward towards my erect cock then to Anna who was busy arranging her towel on one of the chairs.
My wife laughed and said, "Never mind, I'll bring some out with me. Be right back". She left into the house leaving me and her sister with another spell of awkward silence between us. Anna approached the side of the pool where I was still hanging off the edge and slowly eased herself in beside me.
"Burr! It's a little chilly", she said. Her voice breaking the silence made me automatically look towards her and I couldn't help but notice her hard nipples poking out at me. I felt my still erect cock give a twitch at the sight.
"Try swimming around a bit", I suggested, then dove under the water and swam away. Mostly it was an excuse for myself to move away from her. As I dove to the bottom of the pool I tried to clear my head and questioned myself for my body reacting as it just had at the sight of her. I convinced myself it was normal, she was a woman, I was a man, and things like that just happen; that my dick doesn't know the difference between 'out of bounds' and 'fair game' pussy.
I resurfaced feeling reassured and glanced towards Anna who was still glued to the edge of the pool where I had left her and looking lonely. I felt bad. Here she was trying to escape her parents demanding ways, ditched by them for a cruise; connect with her sister and I who were more of strangers than anything, enjoy her summer, and probably feeling unwanted by everyone.
I swam back to her, splashing some water playfully at her when I got close. She smiled at me then quickly returned the act but with much more vigor. I returned with the tried and true double hand method sending a wave of water right at her face. Anna screamed and lunged right at me. In order to prevent her from crashing hard into me, I sort of caught/cushioned her fall. She put her hands against my shoulders and as her forward momentum stopped, her legs sank down against mine, her entire body pressed against me. I could just make out those hard little nipples against me. My still semi-erect cock was trapped between her nice tight, young body and it gave another twitch which she without a doubt felt.
I let go of her meaning to put some distance between us again but she hooked one of her legs behind one of mine, holding me in place. Our eyes locked, her hand trailed down from my shoulder to the center of my chest very lightly. At the same time I felt her push her hips slightly up and against my cock which was growing harder with every second that passed.
"Anna...", I said. It came out hesitant but with an edge of warning.
"Oops, sorry!" she replied. "That foot just got a huge cramp in it! Help out of here, would you?"
"Ah... Ok, sure". She broke away from me and grabbed my upper arm as I swung her towards the pool's edge again. All the while I was thinking what a pervert and an idiot I was. Of course she had a cramp in her leg, why else would she have done that? What was wrong with me thinking she was trying to flirt with me?! I'm 10 years her senior, her brother-in-law, married to her sister... Besides she probably has a boy friend back home that's her age. What boy wouldn't want those perky, round tits... those long, toned legs... that hot, firm ass... Dammit! What the hell is wrong with me?!
As Anna settled into her chair to tan and rub her cramp out of her foot, my wife came out in her bathing suit and carrying drinks. I remained in the water urging my raging hard-on away. Hailey handed me my jack and coke drink which was badly needed, then sat in the chair next to her sister and they began to chat. The rest of the evening went without mentioning. We swam, drank (Anna sticking to plain coke or water), tanned and chatted.
Later that night while in bed with Hailey she kept her promise and fucked me good and hard. The whole time images and thoughts of her sister would push through way through and I had to fight them away. I came harder and sooner than normal with Anna in my head.
That Monday my wife returned to work, leaving me and her sister alone at the house together. Nothing had happened since the pool incident and almost all thoughts of it had left my mind. I spent that Monday morning working in my office alone while Anna watched tv. Around lunch she knocked on my door and let herself in. She sat on top a short metal filing cabinet across from me and complained that she was bored.
As I took a break to talk with her I couldn't help but notice how short her white skirt was. I tried keeping my eyes on hers but they kept drifting back, over her legs, to the hem of her skirt. At some point while my eyes were behaving she had uncrossed her legs. When I roamed back to look I could see far up her inner thighs and just make out the white panties she was wearing underneath.
My cock stirred to life under my desk. I met her eyes again to see a devilish little grin on her face.
"You're not listening to anything I'm saying", she scolded me.
"Um... Sorry, Anna. I just have a lot on my mind right now, I guess". Wow, that sounded lame even to me. Too late to say something better though.
"And what is on your mind that has you so preoccupied?" she demanded.
"Well... Just work, I suppose".
"Work? Are you sure it's work? Because I thought maybe it was me". She stared me straight in the eyes, waiting for my reply. As I hesitated to give an answer she sighed, jumped off the filing cabinet, and approached my desk where she placed her hands and leaned forward. Revealing a nice view of those perfect tits snuggled in her bra.
My thoughts were racing. Was this happening? Is she really seducing me? With what seemed a tremendous effort I pulled my eyes off her cleavage and looked at her.
"Anna... You're a very beautiful girl and soon you will be a striking woman. But... you're my sister-in-law, I love Hailey. Besides, you're too young".
I might have well slapped her with that reasonable statement. She stood up straight with anger on her face. Then pointed her finger at me while telling me, "I see how you look at me. I felt how excited I made you in the pool. Don't tell me you're not into me. How old were you when you started having sex?! Annnd! I never said anything about love! A good fuck is all I want from you anyway. Who better to give that to me than you? My sister trusts you, so you can't be a jerk. Would you rather me go fuck some other man that might rape me, or beat me, or kill me?!"
Her chest was heaving and her finger still pointed at me was shaking from her outburst. She slowly wrapped her arms around herself, her eyes seemed to tear over and she dropped her head. I couldn't let her feel like this just because I sent the wrong signals and wrong intentions to her. I stood out of my chair and went to her. I wrapped my arms carefully around her and she sank into me against my chest. Her hands grabbed the front of my shirt and she held it there clenched in her fists.
I didn't know what to say or do to make her feel good but felt it was my responsibility to fix this. I slowly rubbed my hands up and down her back but she kept her face buried and hidden against me. Finally, she asked if I had meant what I'd said about her being attractive. I told her I did, but she didn't seem satisfied with just that. So, I started listing off all the qualities I thought men would enjoy in her, including her body.
She sniffed at that and asked haughtily, "like what"? Still clinging to me.
"Well", I absently stroked her hair, "like your figure. You're tall, slim, in shape. You have a nice stomach area. Your long legs. Your breasts are good sized and firm". Thoughts of those legs wrapped around me and those tits pressed against me while I pounded her crept into my mind. "You have beautiful eyes" (that I'd love looking up at me), "and nice full lips" (that would feel great wrapped around my cock).
She giggled as she felt my cock growing at these thoughts but neither of us pulled away.
"What about my... You know?" she asked as she pressed her hips into mine.
"Hmm. That's hard to say since I've never seen or felt it". I was rock hard now. My cock was straining against the top of my briefs as it tried to fully stand to attention. As she slightly shifted her body against me again I couldn't help but close my eyes and only half stifle a groan.
Anna released my shirt from her hands and pulled back a little, bringing her hands down my abdomen and stopping at the waistline of my pants. I realized my hands had ventured down and were cupping her ass. She smiled up at me, barely biting her bottom lip, then stood on tip toe and gave me the smallest, sweetest kiss I'd ever had.
As she lowered herself back down I held her skirt and it pulled up just revealing the bottom curve of her ass. I gently squeezed each cheek and she moaned very quietly in approval. The voice in my head was telling me to stop, but the head in my pants was begging me to go on.
Anna sensed my hesitation and pulled my shirt out of pants. She unzipped my pants offering slight relief to my straining cock. Then she slowly lowered herself to her knees in front of me.
I looked down at her, noticing the wet spot of pre-cum that stained my briefs. Her fingers hooked into my briefs and she pulled them down, finally freeing my throbbing member. She smiled at the good size of meat before her before taking my balls in her hand.
Tentatively, Anna squeezed, rolled, and gently tugged them while her mouth placed a kissed on the head of my cock. As she pulled back a sliver of my pre-cum trailed between us. She licked it off her lips while looking me in the eyes. I placed a hand in her hair, behind her head urging her to continue. She obeyed.
Torturously slow she took my cock into her mouth and gagged slightly when she couldn't take any more of it. She sucked back up my length and I jerked and let out a sound of surprise at feeling her teeth graze me.
"I'm sorry!" she blurted and looking downcast.
"Is this your first time giving head?!" I asked. The thought never crossed my mind that she was inexperienced. Not with the sly way she could seduce and drive a man crazy.
She nodded her head, not looking at me.
"Are you a virgin, Anna?"
Again, she nodded her head. She seemed to sink lower, maybe thinking I wouldn't want her anymore, but in fact; I became even more aroused at the idea of being the first inside this beauty. I took her by her shoulders and lifted her up to her feet. My fingers cupped her chin and pulled her head up to look at me. I leaned down to her and kissed her softly on the mouth, my tongue gently parting her lips and slipping inside of her.
Even though she was a virgin she must have had many hours of kissing practice. She matched my intensity, her hand stroking my hair. Our tongues playing and her soft moans falling into my mouth. She nibbled my bottom lip and had me beyond turned on. I couldn't stand this any longer.
"Anna, I want to fuck you right now", I panted into her ear.
"Ok" she whispered. Her hand fell from my hair and she stood before me, waiting for me to make the next move.
I pulled her tight fitting shirt off, followed by her bra and then kissed the tops of her exposed breasts while my hands cupped them, kneading them gently. I lowered myself down, kissing down her smooth stomach and slid her skirt off her legs. I was now face to face with her virgin pussy, barely hidden behind her cotton thong.
I kissed, licked and sucked around the edge of her panties. She moaned for more, tilting her hips forward at my mouth. Smiling, I hooked her panties in my finger and lowered them to the floor. Anna reached down covering her womanhood. I gently but firmly grabbed her hands and pulled them away, getting my first look at her amazing pussy. She was shaven bald, her lips puffy with anticipation. I kissed her covered clit, inhaling her scent, and she moaned again.
I wanted to tease and torture her until she couldn't go without my cock inside of her but I couldn't resist her any longer. My cock was aching to feel her, the head purple and leaking pre-cum, throbbing in pace with my heart beat.
I stood, took her by the hand, and lead her to my bedroom. The thought of betraying my wife crossed my mind, but my cock convinced me that if Anna laid on my side of the bed then it was OK. I climbed over top of her sweet, young body, taking in all of her beauty. Anna spread her legs with her knees bent and pointed at the sky, inviting me in to play.
She wrapped her arms around my neck, her head back against the pillow, her neck exposed to me. I sucked on her neck while rubbing the length of my cock between her wet lips. Soon, she was wiggling her hips against me, grabbing my hair and tugging, arching herself under me, her hard nipples grazing across my skin.
I reached down to guide my cock head into her entrance, my dick slick with her wetness. As I slowly and gently eased my head between her lips, into her tight hole, I kissed her on the mouth trying to keep her calm and relaxed.
First an inch, then two; I looked down at her and saw her eyes squeezed tightly shut, biting her lip as she continued to take more of me in. She whimpered and I felt her body trying to pull away from me.
"Shhh, just relax, Anna. It will get better soon if you relax".
I could feel her pussy throbbing all around me, trying to swallow my cock whole. She was incredibly soaked, making it very easy to continue pushing my length into her despite her wiggles.
I kissed up her neck again until reaching right behind her ear. I groaned and grunted as the last of my cock made its way through her tight opening. I held in place, letting her adjust to my girth. Anna's heavy, panic breathing began to slow and return to normal after a moment. I turned her head by the chin to look at me, my thumb brushing over her lips which had teeth indents along the bottom from her biting them. She kept her eyes closed tight, refusing to look at me.
"Anna," I whispered, "the worst is over sweetie. You did very well. Your pussy feels amazing around me, so hot and wet".
She opened her eyes and looked in mine. I kissed the tip of her nose and felt her body relax. Her hands returned around my neck as she kissed along my jaw line. I began moving in and out of her; at first only pulling an inch or so out before pushing back in, but then sliding out my full length, leaving only the head inside of her before plunging into the back of her pussy.
Anna moaned, whimpered, and screamed. She yelled my name, told me to fuck her harder, and other times went silent. She kissed me hard, bit my shoulders, lifted her hips at mine, dug her fingernails painfully into my back and ass. I gave her everything she wanted, everything her pussy needed, and anything I could think of.
She came twice, both times her back arching up, her legs clamping down around my waist, her pussy convulsing hard over my cock. I'd slow down with my thrusting while she rode out each orgasm, then slowly build her up for the next. I was running out of steam, it had become incredibly hot, and we both were sweating profusely.
I abandoned the nice guy method, grabbed her tits in both hands, squeezing hard with her nipples between my thumbs and forefingers and pounded into her hard and fast. Soon, I felt myself on the verge of exploding and let her know I had to pull out since we didn't have a condom in use. But she tightened her legs around me, pulling me deep into her, and told me she wanted to feel me come inside of her.
All hope of thinking straight had long passed and at the sound of her pleading for me to fill her, I released my load into her hungry pussy.
I stayed on top of her while my cock continued to twitch. Anna ran her fingers lightly up and down my back, her pussy clenching, milking out every last drop of me. Finally, I rolled off of her and she curled up with her head on my chest and her leg over mine. We petted on one another and we both must have dozed off because the next thing I knew Anna was shaking me awake, saying she thought her sister was home. I jumped out of bed and threw on a pair of swim trunks while shoving Anna towards the guest room she was staying in. Then I hauled ass to my office to gather all of our clothes and stuffed them into the office closet.
I'd just made it to the back door when I heard my wife calling out to us from the front door. I bolted out and into the pool, frantically scrubbing myself clean of Anna's scent. My wife appeared pool side just as I had finished composing myself and I welcomed her home with my best smile.
"Where's Anna?" she inquired.
"I don't know, probably still napping in her room?"
"You two have a busy day?" my wife wondered.
I just shrugged and dove down into the water to hide my smile as the memories of the day flooded over me.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/first-time/turning-anna-into-a-woman.aspx">Turning Anna into a Woman</a>