Loading...I saw Alison for the first time in a little shop around the coastline from where I live. As you can see from my bio’, I’m a teenaged girl, or woman, according to your views on the matter. I’m also trying to sort out my sexual identity and as you will see from this story I’m reaching the conclusion that while I like, and might one day enjoy men, especially those who know what a woman needs, I tend towards women and in particular those a little older than me. This is the story of my road to that realisation.
I was in a souvenir shop and I saw a woman. She was tall and dark haired with a lovely figure. I’d never really looked at a woman from that perspective before. I’ve been sexually active or semi active for a while. I’d seen lots of girls in my school’s changing rooms and been to bed with one boy which was not deeply moving – in fact he came before he penetrated me so despite my open pussy lips having felt a cock I was technically and as it turned out physically a virgin.
I’d tell you about that in another story but there’s not much to say beyond that. I’d never thought anything was wrong. My girlfriends had told me that when I first had sex with a boy not to expect anything much. Just a funny maybe pleasant or unpleasant ‘full’ sensation at best and pain at worst. Well I just felt wet and unsatisfied. Despite his best efforts he couldn’t make me come. He licked and sucked all my most intimate areas for an eternity and tried very hard to please me, but nothing happened beyond discomfort. It wasn’t that I didn’t like boys. I’d often successfully masturbated to images both real and imagined of their hard bodies and the intimacies I’d hoped to share. I was shy about my legs being open and him looking and in the end he came the minute his cock touched me so that was it in a quick paragraph.
Why Alison? I haven’t the slightest idea, but something deep inside me awoke when I saw her. She was beautiful, that was beyond debate – she still is and we still share a bed, but, again, more of that later. She was there in the shop squatting down looking at something and I could see her panties clearly. I don’t know why I stared. She caught me looking and turned her head smiling but making no effort to conceal her errant undergarment. I don’t even think her undies were very sexy in and of themselves. They were full briefs, mauve in colour and may have been cotton or nylon. Just common or garden panties. They just looked inexplicably sexy on her and I was seriously sprung staring. Her little boy and her mother were with her. The smile she flashed me lit up her handsome face. I’d have guessed her age at about 30. In reality she was nearly twice my age at 35. When she stood she was nearly six feet tall and I would describe her figure as willowy. Motherhood had softened what might have been a very angular figure. She was confident enough to wear jeans that sat on her hips and showed her knickers at the front even when she stood. The little gap between the top of her panties and her slightly diaphanous top showed a white patch of skin about an inch or two wide and again not the skin of a teen like me but a slender milky white midriff softened by experience. She caught me staring again and I blushed.
The next act, I knew, was deliberate. She brushed past me with a simple “Excuse me” and smile as her body briefly touched mine and turning her back again squatted in front of me to look at some nic-nac. There could be no doubt the third time she caught me staring down her pants. She just smiled and got up to leave the shop with her mother and son. As I exited the shop in something of a lather. She smiled at me again as she climbed into her car.
Mapua is a small seaside village and if she lived locally I hoped I might see her again. It took a couple of weeks but I spotted her one evening going into dinner at the wharf restaurant with a tall man whom I took to be her husband or boyfriend. Maybe I’d been indulging in some wishful thinking and got the wrong idea. I knew lesbians who had children and had assumed…Then she saw me watching her and smiled.
I went back home, poured a bath and lay back to made love to myself as if it were her. I touched myself everywhere I hoped she would. My nipples had been aching by the time I got home and by the time I began to rub myself between my legs my breasts throbbed. My orgasm sent water out of the bath and all over the floor and I screamed out.
My mother knocked on the door to ask if I was alright. How embarrassing!
I stammered a “Yes”.
When I was back on earth I got out an just put on a robe. My mother gave me a knowing little smile and said how much she enjoyed baths as well but that I should probably make sure my dad or sister weren’t home next time I decided to ‘take care’ of myself so loudly. She saw me blush beetroot red and told me not to be embarrassed about it, everybody did it but Rachel my sister wasn’t so noisey. How the hell did she know?!
“Everybody did it” – Sure they did they just didn’t make so much noise their mother heard.
I shouldn’t have worried. My mother is very cool – she had me young and is much like a friend. She is someone I could tell about my sexual confusion so I did. She’d guessed I’d been to bed with a boy but was a bit shocked that I’d not enjoyed or really even consummated the sex at all. So we got talking, I poured my heart out and I told her about the woman. She took it well and said it might be something major or just a crush. Then she told me that she had had similar feelings about some women and that the only way to be sure was to try if that’s what my body told me. She looked me straight in the eye as she told me this. As I said, not your average mother. All in all she was pretty cool and gave me a kiss and a hug and told me to get to bed and take care of any itches a bit more quietly next time.
Even if I went to bed a bit frustrated I was happy I’d told someone.
The problem still remained about how to meet the woman who was increasingly filling my waking thoughts and what about the man? Who was he and was I just making a fool of myself? Why did she let me look at her and why did she smile so sweetly at me. Perhaps she just liked to show off, but then surely she would wear something more revealing than simple briefs. More masturbation and a restless night followed.
Next morning my mother spoke to me again about my feelings. She told me quite plainly that if it turned out that girls were my thing I could bring them home just as my sister brought boys home to her bed and there would be no problems. In answer to my unspoken question she told me my Dad was fine about it. She saw my blush and explained that she and he had no secrets, she may have omitted my loud masturbation the previous afternoon but she had told him that his little girl might be into girls and he’d been of the same mind as her. Well at least I was lucky at home. Could I be lucky elsewhere was the question.
I thought it was about a week later when I saw the object of my desire in the distance near the local school and began to walk towards her. Sadly for me she collected her child and drove off without my getting near her. The next time I was near her was a chance encounter at the local Guy Fawlkes evening on the beach. The whole community turned out and I had one of my little boy cousins on my shoulders watching the fireworks and the bonfire.
Suddenly I heard a voice beside me
I turned as I could not look around and there she was. My stomach did a flip flop and all I could do was open and close my mouth without sound.
Her little boy was with her and so when I recovered the power of speech our conversation went like this.
“It’s alright to look as much as you want. I don’t mind in fact I like it. Would you like to meet for coffee tomorrow?”
I stammered a “Yes” and so we were to meet the next morning for coffee.
“My name is Alison.”
“I’m Amanda”
“I look forward to seeing you Amanda.” She smiled and walked off.
Back home I went in a lather of excitement. Because November is warm here so I’d not worn panties so the tops of my thighs had become a little slick. I needed a shower.
After my shower I went back to my room and disrobing, clambered into bed. As I adjusted my pillow something hit my hand. A small cylindrical object with a little bow and a card.
“Christ, Mother!”
She’d bought me a little pocket rocket to help me play with myself and it was small and thin enough fit just inside me without breaking my hymen. It was no bigger than a large lipstick container and as I parted my legs and ran it’s buzzing surface along my slender pink inner lips up to my clit things went all melty inside me. I had to put the pillow over my face to muffle the noises I made.
The next morning once Dad and my sister had gone. I went and thanked her blushing again.
How would things go with Alison was my next uncertainty. What was she? Would I be played simply for her pleasure.
I wandered along to the coffee shop and there she was. She got up took one of my hands and kissed me on the cheek.
She told me how glad she was I’d joined her. There was a lot of small talk and then in the midst of an innocuous exchange there was a silence during which she looked at me.
“I liked you looking at me. Did you enjoy it?”
I didn’t know where to look or what to say. I blushed and looked down.
“Yes but I’m not sure about anything.”
“That’s fine. I don’t want to push.”
“What about the man- your husband?”
“He’s fine about my ways. I love him so much that nothing would ever come between us. Anything I do he knows about. So consider that, Amanda, before you do anything beyond having coffee with me.”
I was flustered. So I asked for a few more details about the relationship. Alison was deeply in love with her husband and just had needs he couldn’t fulfil.
She was into girls especially younger ones about my age and sometimes if they were agreeable she would share them with her husband, but usually not.
We sipped our coffees and there was an uncomfortable silence.
Alison broke it saying that her mother was babysitting for her today and that if I liked we could wander down to her house and relax out of the public eye
We walked down the road together and upon reaching Alison’s house she took my hand and we walked down the secluded path to her front door.
“I prefer not to advertise to openly in a small community.” She said with a smile as she squeezed my hand.
Entering the house which had a great view out over the beach and coastline she showed me around and we ended up on the deck outside looking at the deserted beach and sitting side by side on a big sofa that had obviously been put out there that morning. Again Alison broke a silence to ask what I would like to do with the day. I lost my nerve completely and just shook my head saying I didn’t know.
“Well Amanda I’m going to go and get some wine and we can have a few drinks for lunch and see what happens.”
She kissed me on the cheek and got up to go and get a bottle or as it turned out two. When she came back she had disposed of her hipster jeans and was just wearing a tight fitting black cotton singlet and a pair of matching black cotton panties. It was my first chance to look at her legs and how long and beautiful they were. These panties were different from the pair that had caught my attention. They were not a g-string but quite small, just a piece of material front and back joined by a black string. They looked fabulous against her white skin. I could see about four inches of her stomach and her nipples poked through the front of her top. Looking down between her slightly parted legs I could see the swell of her pussy.
With her legs drawn up slightly the panties did not quite cover the outside of her lips. I couldn’t see any hair and as she raised her arm to run her fingers through her hair I could see that under her arms there was no evidence of shaving. She saw me look and simply said
“I had my armpits zapped and few other areas too!”
There was a pause.
“Do you like my undies?”.
There was a further silence as I nodded.
“I changed just for you to enjoy my body. It turns me on to have you look at me so have a drink and look as closely as you want. Don’t forget to touch if you’d like.”
We were now sitting facing each other with our legs drawn up. Given I had worn a skirt my lacey panties were on display. I felt warm and horny and nervous all at once.
Alison looked down between my legs.
“I like your panties. What do you do about your hair?”
I just blushed.
It was obvious, given that the front pannel of the panties was transparent, that I had a good patch of hair. I’d never had to shave for a bikini but I did trim with a scissors especially in summer, just to keep cool really. Alison set her drink down and reached under herself. Lifting her hips she pulled her panties down.
“I used to have quite a lot of hair that went right back to ‘you know where’ but a girlfriend of mine gave me a trim one day and I was hooked on not having anything on my lips or back there and I’ve had no complaints.”
She sat across from me her knees apart and sipped her wine. “Would you like to see my breasts?”
“Yes.”
“Then you’ll have to come over here and take my top off.”
Nervously and none too gracefully I got up and knelt into her. It was not an easy position and I lost my balance and wound up against her, my cheek on her shoulder. She cradled me and kissed me lightly.
“Here Sweetie.” She cooed and lowered one of the little straps holding her top up. Her left breast was right in front of my face. She had dark nipples with thick eraserlike nipples probably as a result of nursing.
“They grew when I was breast feeding and now I love to have them sucked.” She said cupping her breast and offering me a nipple.
I took it and closed my eyes as I closed my lips around it. As if second nature I suckled on Alison as she held me. She sipped her wine and kissed me stroking my head and torso as she ‘nursed’ me. I don’t know when I first noticed but a steady rhythm disturbed me and I opened my eyes to find Alison stroking herself her eyes closed and her head back. I continued my suckling. My insides were churning with excitement and I knew that I was damp. I closed my eyes again and stayed at Alison’s breast. She began to breathe deeply and after a frantic rubbing between her legs gave a gasp and stiffened with a little sigh. I felt my own slight contraction. It wasn’t really an orgasm, more like an involuntary twitch inside me. The result was I bit Alison’s nipple softly. Her legs shot out straight and she had a second more powerful orgasm. She lifted my face to hers and kissed me deeply. I could smell something akin to my scent when I made love to myself. As our mouths and tongues sought each other I felt a finger slip into my mouth. Both our tongues licked and sucked it, my first taste of a woman.
We cleaned Alison’s juices from her finger. She tasted like nothing else. It was subtle and thick and I wanted to taste more. We kissed and hugged for ages maybe an hour without saying anything. The sun was high in the sky and it was warm. Stretching Alison asked if she could ‘see’ me.
I sat up and pulled off my top. I had not bothered with a bra. My breasts are not huge and are very firm so I can get away without wearing one. We had been together for nearly two hours and my breasts ached. My nipples stood out like little pink diamonds and there was no doubt that the gusset of my panties was very moist. Alison asked me to get up and lie forward onto the sofa on my knees. I still had my skirt and panties on and made to take them off but she stopped me. She handed me her panties and I put them to my nose. Then she pushed me forward and told me to close my eyes. So I was on my knees with my short skirt riding up as I knelt forward and my face buried in Alisons slightly damp and scented cotton panties.
Hands rubbed my bare back followed by a trail of kisses. Next a hand went between my knees and I knew to spread my legs. The hand was gone to be replaced by lips on my ankle. Kisses made their way up my calf to the back of my knee. Then the same happened on the other leg but this time the kisses went up the back of my thigh to the egde of my panties. I was breathing deeeply but still steadily. My pussy felt so tight and my clit begged for a touch – even mine. Alison went back to my other knee and kissed up the back of my thigh. My skirt was thrown up over my back. Her tongue then outlined my panties and pushed them up between my cheeks. I panicked as the tongue ran up the crease of my cheeks. I clenched.
“It’s okay Baby. You’re lovely and clean just enjoy what I’m doing, let yourself go.”
There was a tug on the material of my panties and a cutting sound. She had used a knife or scissors or something to cut the material that was my last vestage of modesty. Both of my most secret places were visible as she made gentle soft oral love to me.
“Open wide.” she whispered and as I did she spread my cheeks and my anus felt her tongue.
I cried out as the orgasm hit me. I went rigid and clamped on Alison’s face. Alison’s panties were wetted further with my tears and much as it embarrasses me some dribble from my mouth as I lost control. I managed not to let my bladder go but after coffee and wine and two or more hours of making love I needed to go.
I was unsteady on my feet as Alison took me by the hand to her bathroom. We both went and then used her bidet to wash ourselves. I kissed her and tasted myself on her face.
I told her about my embarrassment at her touching or even seeing my open rear. She reassured me that I was clean as a whistle and how she had enjoyed taking my anal virginity. She said I had one or two stray little hairs she’d take care of one day. I blushed at the mention of this and my virginity. I told her that I still had my hymen and now that I was with a woman would probably be keeping it. She giggled and shook her head.
“Not necessarily Baby. I can take your cherry if you like. I’ve got a toy I like to wear if you’re game, but it’s getting on and I must collect my son. If you want to come back tomorrow we can make love tummy to tummy or if you want to save it for a man, I’ll understand if you want to.”
I just blurted out that I wanted her to take me. We kissed and cuddled and tried to get dressed but it took an eternity. I elected to go home without any panties, Alison offered me a pair but I declined.
I got home at 3pm and my mother took one look at me and knew.
“Are you alright?” She asked.
“Yes fine. Just going to take a bath”. I smiled.
She smiled back.
I slept badly that night. I was nervous and excited that after my one abortive attempt I would be a virgin no more by sundown tomorrow.
By morning I was an emotional mess. I was due at Alison’s at 9 and the minutes dragged. Finally at about 8:30 I set off down the road. I wore white cotton panties that day as some sort of symbol I suppose. We didn’t have an easy time of it as it turned out.
I went up to her door and knocked. I nearly fled I was so nervous but the door opened and there she stood in just a cotton t-shirt and jeans her panties just visible above her hipsters. She held her arms out to me and I melted into them. We kissed and she took my hand leading me to her bedroom. On her bed on my back my legs apart she made oral love to me until I screamed. She asked me if I really wanted my maidenhead gone and I nodded.
I saw the soft leather harness and the ‘cock’ she intended to use on me sitting on her bedside table. They sat there as we had made soft wet love for about two hours. I lay back recovering from my final orgasm. Alison fitted herself into the harness and climbed up on top of me. We kissed for ages as she pressed gently against my entrance. I felt a bit full and stretched even as she cuddled me with just the head of it inside me.
I wasn’t comfortable physically. I was in heaven emotionally and so physical discomfort meant nothing at that point. My legs were wide open, my sex was at Alison’s mercy and I would not have had it any other way.
My body failed me. I had a thick and persistant membrane inside me and every little push hurt. Alison saw me wince with her preparitory thrusts and told me she wanted to stop. I was determined that I should be hers in every sense and told her to just that.
“Do me now! No matter what, I want you to have me.”
Alison kissed me deeply and asked me if I was certain I wanted to go ahead. I bit my lip and nodded. She gave a thrust with her hips and I was a virgin no more. But God Almighty! The pain. It was like a needle in my core and the stretching was actually too much. I cried out and my tears ran. I couldn’t control my emotions. I hurt. I really did – some of the worst pain I’d ever felt. Aside from that there was the emotional bust of giving myself to someone. I lost control and howled like a baby as I bled onto the phallus that had transformed me. Alison was horrified and pulled out. Her ‘cock’ was stained with my blood. She began to cry and begged me to forgive her cuddling and crying with me. I was in pain and crying but she became almost hysterical saying over and over “What have I done to you? God forgive me.”
I wound up comforting her. I don’t know if I will ever experience such emotions again. My friends tell me childbirth is similar emotionally. I cried and felt pain and loved the person who had hurt me all at once. She cried begged for forgiveness and, I am sure, would have gladly whipped herself for what she thought she had done.
I did bleed but the pain did subside but I had to spend an hour reassuring Alison that I had nothing to forgive her for. She had made me a woman and shown me such love. My body had let us down but it was over and soon we could make love as often as we liked.
She unhooked the straps and threw the harness and the dildo across the room vowing to burn it. She lay face down beside me sobbing, her face in the sheets. I lent over and kissed her bottom. I moved slowly out kissing every part of her flesh I could reach. I must have kissed her for an hour before she rolled over to hug me.
“I’m so sor..”
I forced her face to mine and my kiss stopped her. Soon we were actively embracing and I knew that I was going to make love to Alison. I’d looked and watched but never touched her between her legs, yet my kisses led me to between the lips of her sex.
She looked so different to me. My pussy is a small mound with almost a pout and you can just see my inner lips when I’m not aroused. Alison was, of course as a result of her routine, hairless on her lips and they were longer and thinner than my outer lips. There was no hint of anything beyond them until I pried her legs open and could look and lick all the way from her tight pucker along to her lips and up to her clit. I knew what I liked but had to ask Alison to show and tell me what she wanted. I’d been with her when she masturbated but I’d been suckling her breast at the time and not watching her hands. Her breathing was picking up and she told me to lick my fingers and put two inside her, then to press against the front wall of her passage. As I did this I felt her settle on my upturned fingers. Her clit was at my lips and she asked me to suck it gently until it felt really hard and then to flick it with my tongue until she begged me to stop. Alison’s rolling orgasm began after about ten minutes of my amateurish ministrations and just kept going. I felt her contract on my fingers and the inner flesh my fingertips pressed against was so hard!
In between climaxes she gasped out that she wanted me to do this while her husband fucked her arse. I shivered either with nerves or anticipation. I’m not sure but couldn’t say anything without letting go of her clit. With a final thrash Alison went rigid and reached to pull my fingers from her. If I had not been so sore I would have either masturbated for her or sat on her face. Alas I was not in any state for that. You can imagine my embarrassment when Alison got up groggily and told me that she had to clean up the mess she had created. My pussy looked a bit red and there was a small smear of blood at the bottom of my opening. I was pushed onto my back and before I could protest her soft tongue snaked from my anus to the middle of my lips. It pried me open and softly lapped me. It was strangely non-sexual just a loving act as Alison cleaned my tattered little pussy. She bathed my opening and each lip completely. The last act I remember was her pulling up a duvet and covering us both. Offering me her breast she cuddled me begging forgivenes again, I fell asleep.
Voices woke me, one was familiar but the other deep and masculine. I feigned sleep and listened. It must have been her husband.
Alison was whispering to him that she had hurt me terribly and was worried I’d be scared of her from now on. She told him most of what had gone on and began to sob again. I heard him kiss her and warn her not to wake me before he got out of the room. On cue I stirred and rolled over to hug her telling her I loved her. We kissed for ages and then I heard a door open.
Alison asked if I wanted to meet her husband. I nodded and she pointed to a robe. Our clothes were God knows where. Alison called out for Tom not to come in as I was naked. She got out of bed and strolled out to ‘greet’ him. I was embarrassed and had to be called out. Well if men were your thing or even not you’d certainly remember him. He was a good 4 inches taller than Alison and while trim, looked quite muscular. He was blond and bronzed. Alison was still naked and her pussy was obviously wet.
“Tom is wondering if you’d like to stay the night? It would be lovely if you could.”
“Do you mean share your bed or just sleep over?”
“Which would you like?”
“I’m too sore to do anything but I’d like to sleep with you Alison, if Tom doesn’t mind sharing.”
A grin crossed his face.
“Don’t you get any fancy ideas Darling I really hurt her very badly – it’s just you and me for sex tonight.”
My tender little core contracted at the thought of watching.
“Let’s organise dinner and have a swim before bed.” Alison suggested.
I blushed
“If I’m out for the night I should ring home and let my parents know I’m staying the night.”
They both smiled and Tom handed me the phone.
To my horror when I rang home my father answered. I didn’t know what to say and went silent after my “Hi”, but he was so sweet. All he asked was if I was alright and said it was fine if I stayed and, I heard him pause, then.
“Just ring in if you’ll be away tomorrow night so we don’t worry. I want you to know that I….we all love you very, very much. Do you understand that? I want you to be happy, that’s all.”
He hung up.
I began to think I’d underestimated him. I’d always loved him but never been close in the sense that I could talk to him like my Mother, even obliquely, about my sexuality. Maybe my mother was right that I could trust him and should not underestimate his love for me.
Tom made a light dinner while Alison and I talked over what had happened that afternoon. She was still very upset. We ate we had a few wines and then headed down to the beach. It was twilight by now and so we skinny-dipped. I was curious about Tom and had a good look, as he did at me. We caught each other and laughed. I assume he liked what he saw as his cock began to grow. I’d only seen one other cock and his was different. He was circumcised and looked inviting. As I felt my attraction grow I came to realise that maybe it was men and women for me and that I shouldn’t try to pigeonhole myself. I hadn’t enjoyed sucking my only boyfriend’s cock but I was feeling an urge to take Tom in my mouth. Maybe it was his firm body, maybe the clean look of his cock, maybe it was that he was a man and not a boy. Alison and I cuddled in the water and Tom came and held us both. I felt his cock hit my bottom only to have Alison reach down and grab him telling him firmly that I was too sore for any of his nonsense.
We played around for twenty minutes and wandered back up to shower together. I washed Tom’s cock while Alison watched and stroked my breasts. His cock felt warm and hard and I knew that when I was healed that it would want to have it. It wasn’t as big as Alison’s trashed strap-on so I felt confident that I could have it inside me. The next stop was their big bed. There was a brief moment of discomfort as we sorted out who went where. Tom and Alison faced each other and I was behind Tom with an arm around him watching as he began to kiss and make love to Alison. It was different but really sweet to watch two people who clearly loved each other spend the night wrapped up in their own little world of love. What happened that night and for the next few months will be the basis of my next story if you’re interested – just let me know.