Deflowering Tara

Tara is the daughter is one of our close friends, Anne. They live just down the street from us. She is a shy 19 year old girl and, although very pretty, always wears baggy clothes that hide her figure, rarely combs her fair and even more rarely wears any makeup. But even 'au naturel' she's very pretty. She comes over to our house regularly with her mother and even as a younger teenager was always lovely to talk to - well versed in current affairs and knowledgeable in various other topics. Overall a very intelligent young woman. She had no problem talking to us as she knows us well but her mother had told us that she has very few friends She doesn't mix well with her peers and other kids her age mistake her shyness for disinterest in interacting with other people her age. She's very few girlfriends and has never had a boyfriend at all.

Last month I came home late in the evening and my wife Kelly, Anne, and Tara were in the living room all enjoying G&Ts - even Tara who I'd never seen drink before. I wasn't going to be outdone so after checking they were all ok with their current drinks I poured myself a Tanqueray and tonic with a slice of lime. We all chatting and after a little while Tara left to go the bathroom giving me a shy smile as she left. It was an odd smile - I knew her well enough at this stage and hadn't seen that particular look before. She looked almost embarrassed for some reason. Added to that she was wearing a reasonably tight fitting dress which was most unlike what I'd seen her in up to now.

After she left my wife and Anne went silent and looked at each other. I had no idea why. I tried to make eye contact with my wife but she wasn't having it. The whole feeling was a little odd. After a short while my wife nodded to Anne and only then did they look at me. To say I felt under a microscope would be an understatement and I still had no idea what was going on between them. And then Anne threw a bombshell at me.

"Will you sleep with Tara?"

I sat there stunned into silence. Did I just hear that right? I looked at my wife. She turned her head to me and nodded. Sorry what!? My wife wants me to sleep with Tara? That can't be right! I stared at both Anne and Kelly trying to understand what the hell was going on.

Anne smiled and softly said "let me explain".

I nodded still unsure what this really was.

"You know Tara is very shy." Anne said. "She's never really come out of her shell and has never even had a boyfriend. You also know we are sex positive parents like yourselves."

She was right. Our daughters - now in their twenties - were always brought up as sex positive and have never been afraid to discuss things with us. I don't mean details of their sexual liaisons but not afraid to talk about sex in general, to ask questions about different contraceptives, and even now - while 24 and 26 - to talk about their boyfriends and their sex life in general terms. But still - this was unexpected.

"I've spoken with her about sex" Anne said. "She has decided her first time should not be a drunken fumble with a teenager but should be with someome she trusts and respects and who will teach her about sex. She didn't mention you specifically but I knew who she meant so I spoke to Kelly first. We both agreed that Tara meant you and we also both agreed that it should be you."

Me! Anne wants me to be her daughter's first sexual experience. And more surprisingly my wife appears to agree. I looked at Kelly questioningly.

"I don't know why you're surprised," she said. "I know you find her attractive and who better to teach her to love sex that you? You know how to pleasure a woman - I can attest to that."

"It's not that," I replied. "It's that you don't seem to have an issue with me sleeping with another woman."

"This is a special case," Kelly told me. "You ... we would just be helping a friend. Now agree to this and go upstairs and look after Tara. We'll be here to support her if she changes her mind. You don't need to worry about that".

It was only then I realised that Tara hadn't come back from the bathroom. I looked at both Kelly and Anne. They both smiled at me encouragingly and I realised then that Tara had been part of the planning of this. She was upstairs in our bedroom waiting. And both her mother and my wife meant this to happen now - while they waited downstairs in case they were needed for Tara. Obviously I would not force myself on her - but if she had second thoughts she would need these two women to let her know that that was ok too.

"Are you sure Tara wants this?" I asked Anne.

"Not 100% certain," she replied. "But she's certain enough that she wants to try and she's waiting for you upstairs."

"Well," I said. "I'm not going to pretend this isn't weird but I will say that I'm honoured to be asked."

With that I left the room and went upstairs. I was afraid to say anything else to Anne and Kelly in case I said something stupid. I walked into our bedroom and Tara was sitting on the edge of the bed facing the door. She looked extremely nervous as I walked across the room and sat beside her. We both sat there for a couple of minutes silently. She was too nervous to say anything so I broke the silence.

"Tara,"I said gently. "Anne has told me that you want me to help you learn about sex. Is that that you want?"

She looked at me with her head slightly bowed and nodded wordlessly.

"I would be happy to help such a beautiful young woman as you." I said.

She dropped her eyes and mumbled something. I asked her what she had said.

"I'm not beautiful." she repeated.

I didn't say anything. I just stood, took her hand and lifted her to her feet. She stood and looked me in the eye.

"Come with me." I said and led her to the full length mirror in our bedroom. I placed her in front of the mirror and stood behind her. All she and I could see was her in her the green summer dress she was wearing.

"Look at yourself," I told her. "You are stunning." I took my hands and held her head. "You have beautiful long brown hair and a pretty face."

I slowly moved my hands down across her shoulders describing he as I went. As I told her she had firm, perfectly shaped breasts my fingertips gently caresses the outside of them. Sliding my hands down I commented on her narrow waist and flared hips. I moved my hands back and cupped her ass telling her how fine and firm it is. With my hands there we both looked down at her shapely legs underneath her thigh length dress. I leaned forward slightly and gently kissed her neck.

Moving up to her ears I said "Trust me. You are beautiful. Now are you sure you want to do this. I will stop any time you say." She made eye contact with me in the mirror, her breathing slightly heavier.

"Make love to me please", she whispered.

Without another word I lifted my hands to the rear zipper of her dress and slowly started pulling it down. I could see her breasts gently rising and falling in the mirror as I fully open the zip. Placing my hands on her shoulders I slid the dress off them. I could just see her cleavage in the mirror as I continued to kiss her neck and ears, gently nibbling her earlobes. I rubbed the dress down her arms and it slid over her breasts and eventually fell to the floor. My breath caught in my throat looking at her standing there in black lace bra and panties.

"Absolutely gorgeous." I told her.

She had a slight flush in her cheeks and I could see her nipples starting to poke through her bra. I unclasped her bra at the back and slowly slid the straps down her arms. It caught on her nipples for a moment then fell to join her dress on the floor. Her orange sized breasts still stood firmly with her nipples sticking out a quarter of an inch. I cupped her breasts with my hands and rubbed my thumb over her nipples. Her lips parted slightly as her breathing deepened and I ran my lips and tongue over her neck and shoulders. Slowly gliding my hands down her sides to her hips I hooked my thumbs into her panties. I looked at her eyes in the mirror. She hesitantly nodded so I slid her panties over her hips and down her thighs revealing her sex. Her pubic hair was trimmed neatly and in the mirror I could see some dampness around her lips. I let her panties drop to the floor and removed my hands from her.

I stepped back moving slightly to the side of Tara and unbuttoned and removed my shirt. Tara watched me silently in the mirror as I undressed. Kicking off my shoes I opened my belt and unbuttoned my trousers. Letting them drop to the floor I stood there in my boxers and Tara's eyes drifted down in the mirror to my erection tenting my shorts. Hooking them with my thumbs I pulled them down exposing my erection to her gaze. Her eyes widened when she saw its full size. I'm no porn star but my cock is a good 9 inches erect and wide enough that the petite Tara wouldn't be able to get one hand around it fully. Placing my hands on her shoulders I turned her to face me. She couldn't take her eyes off my cock and had a fearful look on her face. Lifting her chin with my hand I brought her eyes up to mine.

"Remember Tara," I said. "You can stop whenever you want. I will not force anything on you. And your mother is just downstairs - you can call her at any time".

She bit her lower lip nervously and, hesitantly stepped towards me only stopping when my erection touched her belly. Still looking in my eyes she gently placed her hand on it.

"I do want this," she said softly. "But it looks so big. I'm not sure it will fit in me."

"Trust me," I smiled. "It will fit after I get you ready for it."

Still with her hand on my cock she smiled into my eyes as I leaned forward to kiss her. Our lips touched and I gently pressed my tongue to her mouth. Her mouth opened slightly and I my tongue entered to touch hers. I placed my hand on the back of her head as we kissed. Her hand left my cock and both arms went around my back as she leaned into the kiss. I moved one hand around her waist and pulled her into me. Our bodies held against each other - my cock pressing into her belly and her hard nipples pressing into my chest. We continued to kiss harder as I moved both hands to her beautiful ass and gently squeezed her. She gave a small moan into my mouth and held herself even harder against me.

Reluctantly I gently removed my mouth from hers. Her mouth stayed open as she gently panted, her eyes locked onto mine with absolute trust. I took her hand and we moved over to the bed. She sat on the edge which brought her face level with my hardened cock. She stared at it so close with her mouth slightly open as she licked her lips.

"This is the first penis I've seen." she said nervously. "Well in real life anyway. I did watch a porn film once but it didn't seem real then."

"Well this is the real thing if you want to look closer," I replied. "We have as long as you need."

Tara glanced up to my eyes and back down to my cock as she took one hand and placed it on the shaft. Her fingers couldn't go all the way around it. She gently moved her hand up and down and looked back up at me questioningly. I smiled down at her and nodded to let her know that she was doing fine. She took her other hand and cupped my balls, gently squeezing them. The feeling was fantastic and my cock jerked giving her a little start. She bit her bottom lip again watching the foreskin move back and forth as she slowly jerked me off. Her face moved closer as she leaned forward to get a better look. Then, completely unexpectedly, she opened her mouth and stuck out her tongue to like the tip. I gasped a little and she looked up at me asking if she'd done wrong. I told her that what she was doing was perfect. She smiled and went back and licked my cock head again, rubbing her tongue all over it. She must have seen this in that porn she watched and wanted to try it. After a minute of this she stopped and I could see her hesitate. Then, a look of determination on her face, she opened her mouth leaned forward to take the head into her. Sucking gently she ran her tongue over the tip again while still jerking me with her hand. I made a small moan at the sensation. Looking down at this beautiful teenager with my cock in her mouth was a dream picture. She continued to squeeze my balls and wank my cock and I could feel my erection get even harder in her mouth. She had just the head in but the feeling was amazing as her tongue pressed all over the head. Her first blowjob and she was a natural.

I let her do this for a few minutes then took her head and lifted her off my dick. She looked up at me with her mouth still open and asked if she was doing it wrong. I told her that she was doing it all right but I wouldn't last much longer if she continued.

"I've never seen a man orgasm either," she said. "I'd like to see it in real life. Would you still be able to make love to me if you do now?"

Would I? I'd say I would stay hard all night regardless with this beautiful woman naked in front of me. I nodded that I would and she smiled moving her mouth back to my cock while maintaining eye contact with me. Her saliva ran down my dick lubricating it for her hand, increasing the pleasure. She sucked harder and started moving her hand faster. I was definitely not going to last long as she continued to give me her first blowjob. I placed my hand on the back of her head and gently pressed. She took the hint and took some more of my cock in her mouth. She got about half in before stopping started moving back and forth along my hardness - her tongue continuing to lick all over the cock in her mouth.

With one hand still rubbing my cock and her other squeezing my balls I could feel my cum rising and I moaned. She must have realised how close I was as she sucked harder and jerked faster until I told her I was about to cum. She took her head off my cock leaving just her tongue pressed against the base of the head as she moved her hand faster and faster. I looked down and saw her staring up at me watching my reaction. When we made eye contact with my cock at her mouth I fell over the edge. My cock exploded into her mouth with ropes of cum hitting her at the top of her throat. Her eyes widened and she looked down at my dick still shooting cum at her. One blast went on to her chin but the rest straight into her mouth and she closed her mouth over my cock again to take it all. When the power of my orgasm receded I placed my hand on hers to stop her jerking me and she slid her mouth off my dick and closed her lips to swallow. I was stunned. Not only was that a tremendous orgasm she was swallowing my cum on her first time. A small amount fell from her chin on to her tits.

"Not as icky as I thought it would be", she giggled, looking at the cum on her chest. "Was I good then?" she asked.

"You were amazing Tara," I panted. "Are you sure that was your first time. You are a natural cocksucker."

She beamed in delight and said she'd been wanting to do that since she saw it in that porn film.

"Sometimes I've masturbated thinking of sucking a penis," she told me. "But I had no idea that it would feel this good. And I'm not sure I've ever really orgasmed."

"You'd know if you had," I told her. "Very shortly you will know what a real orgasm is like."

I got my shirt from the floor and used it to wipe the cum off her tits. Discarding the soiled shirt I leaned over and kissed Tara on the mouth. Then gently lay her down on her back on the bed. A little nervousness returned to her face as I got on the bed and lay beside her. Putting one arm around her I kissed her again as I gently ran my hand over her sweet breasts, rubbing her nipples and gently pinching them. She gasped in to my mouth as I teased them. I took my mouth from hers and smiled at her. She nervously smiled back as I told her that she could still stop anytime she wanted. She shook her head and told me she wanted this.

Sitting up on one arm I leaned over and kissed her right breast, gently sucking the nipple into my mouth. My other hand teased her left nipple. She gave a little gasp at the dual sensation. Still teasing her nipple with my lips and tongue I slid my hand over her belly and down to the top of her pubic area. I looked up at her and she nodded ever so slightly. I moved my hand over her hair to the treasure between her legs. I could feel the dampness of her arousal on my fingers. Taking one finger I pressed gently pressed at her entrance and her lips parted to let me in. She gave a little moan at the first time anyone had put anything in her. I sank my finger in fully feeling her warmth and slowly moved it in a circle pressing against her walls. Leaning over her I started playing with her left nipple, sucking and nibbling at it. Her breathing got heavier and she was starting to make some small gasps. I withdrew my hand and added a second to her entrance. As I slid in with both fingers she moaned again. They slipped in easily as she got wetter while I manipulated her with my fingers. With both in her fully I hooked them upwards to reach her g-spot. I found the small hard spot and gently rubbed it with both fingers. Tara opened her mouth and let out a gasp as I felt her nipple get harder in my mouth. I started moving my fingers in and out of her, slowly at first and then faster. She was now starting to pant but not ready for an orgasm yet.

Removing my fingers from her I rolled on top of her putting my legs between hers and propping up on my hands to look down at her. She stared up and me with desire mixed with a little nervousness. Leaning down to kiss her I then ran my tongue down her neck to her nipple and started sucking on it. I moved to the other nipple as she closed her eyes again and gave little moans. Sliding down the bed I ran my lips over her belly to her navel and put my tongue in it licking it gently. I then continued my journey downwards until I reached her thighs. Her legs wide open I gently kissed her inner thighs, from one to the other, slowly getting closer and closer to her pussy. She was now panting in earnest with the occasional moan escaping her lips. I continued to tease her, getting closer and closer while circling around her vagina - never actually touching it. Until finally, I moved my mouth in and put my tongue inside her. She gasped and moaned as I used my tongue like a mini-cock to taste her. She tasted divine. Gently I withdrew my tongue and moved upwards to her sweet spot. I reached up with one hand and pinched her nipple as my tongue found her clitoris. The hood was fully back and I licked it gently as she made a small cry.

For a moment I thought of my wife and her mother in the room below and wondered if they could hear us. Well they knew what we were doing up here so I put them out of my mind and focused on pleasuring Tara. Taking my hand from her breast I put both arms under her thighs and lifted her knees over my shoulders to get better access. With my tongue moving in a circular motion on her clitoris I placed two fingers at her entrance and gently entered her again. Her cries got louder and more frequent and she put both hands on the back of my head. I continued licking her button moving my tongue faster as my fingers plunged in and out of her pussy. Pushing the fingers in fully I sought her g-spot again and started rubbing it in time with my tongue on her clitoris. Her fingers curled in my hair as her cries got louder and louder until the damn burst. She gave a scream of pleasure as her orgasm washed over her. Her juices flooded my hand and her pussy spasmed on my fingers. I continued to lick her as her whole body tightened and then felt a second orgasm hit her as she moaned loudly again. I slowed my tongue action and gently removed my fingers from her pussy which was now soaked. Finally stopping on her clitoris I rose up to her face and kissed her. Her hands grabbed the back of my head as her tongue launched into my mouth doing battle with mine. She pushed my head back and stared in to my eyes. Her whole face was filled with lust.