Terry Ch. 01: Losing Virginity

This is the story of Terry unexpectedly losing his virginity to a mature lady many years his senior, certainly not in the way he wished.

My grateful thanks for the help I have received with the editing of this story.

-o-o-

I was in foster care from the age of eleven to seventeen and stayed on paying rent to my foster parents till I was nineteen. I kept in touch with them after I moved out.

I offered a lift when they said they were going to a friend's party so they didn't need to worry about drunken driving or taxis. When I dropped them off I mentioned to the host I intended going to the cinema and confirmed it would be ok to collect them afterwards.

I returned about 10:45 and was promptly handed a beer drawn from a party7 can, and joined in chatting to several people I knew, especially Annette and Gisl.

Annette is a slim Portuguese lady. I had known her for eleven years as she had been a regular friend of my foster parents. She had long, curly bleached hair and always wore low cut tops. Through my formative years she had greeted me with a big hug and as I'd grown my face progressed up her body, but always seemed to find its way to her almost nonexistent cleavage. She divorced around the time her youngest was born and became a single mum of three, at that time they would have been around fifteen, thirteen and nine. I distinctly remember the way her cleavage improved quite dramatically when pregnant with her youngest and the hugs always felt so much stronger at that stage. In the last three years or so since I had seen her, she had put on a little weight on her tits. I'd had a crush on Annette for a while and had often fantasised about shagging her. That evening her shirt was particularly low and wide cut and more than once I enjoyed getting a tiny glimpse of dark nipple, just a tiny hint.

Gisl was Annette's mother. She was a much older and heavier Portuguese lady with much, much, bigger tits. I had met her a few times over the years but never got to know her. That night she was wearing a yellow dress and a glass of red wine spilt down the front.

The drink had made all of them quite happy and the conversation was very suggestive, especially what the two women would like to do to me, much to my embarrassment.

As the party started breaking up there was talk of phoning for a taxi for Gisl and Annette as their lift had been called into work on a call out. I asked where they lived to see if I could offer a lift and as it happened neither of them were very far off my route. There was a babysitter involved who was Gisl's neighbour.

The first stop was Annette. I walked with her to the back door and helped get the key in the door. She went straight to the bathroom telling me to wake the babysitter who was curled up on the sofa. She pretty much woke up and went to the car, probably to get away from this strange guy. Annette returned and we said our goodnights with a particularly nice hug and sloppy, drunken kiss which got this twenty-two year old shy virgin's pulse racing.

Nervously, with my arms still round her waist I asked, "Can I come back when I've dropped your mum off?"

"Really?" There was a surprised look on her face, "Why would you want to come back?"

I tried to splutter a reply about the earlier conversation.

"Hey Terry, I'm going to go to my bed, but if you're allowed to return and knock on the door, I will answer it and let you in."

"What do you mean 'if I'm allowed'? I don't have to ask permission or explain to any one."

"I know, I know, ok look, if you knock, I'll open the door. You may have to keep knocking to wake me but I will answer."

Another hug and kiss "See you soon."

I got back in the car with a knot in my stomach and a smile. Drove to my foster home, walked mum & dad to the door and said our good nights then continued the journey and parked outside Gisl's garage.

"Could you do me a favour and look at my curtains. I can't close them and can't see what the problem is?" I didn't want to get involved with her mothers house repairs, thinking I really needed to get away quickly to return to Annette.

"Yes I'll have a quick look."

"Make sure you lock up properly, we have had some problems along here."

Gisl's house was up some twenty-five steps from the road level and she was quite merry so the babysitter helped me guide Gisl to the door. I took the key from her and unlocked the door.

"Take 'babysitter' over then come back for the curtains."

I followed the girl through the gate in the fence between the two houses and saw her into the door then returned to Gisl, thinking 'I really really don't want this to take long'.

"Where are you?" I called out as I entered the large hallway.

"Up the two steps," I followed the voice to Gisl in the bedroom by the window and had a quick look at the curtain track; one of the clips had been fitted incorrectly and had twisted round.

"Have you got any screwdrivers?"

"In the hall cupboard, come with me."

She left me at the cupboard; I chose a couple of tools, returned to the curtain track and started dismantling it. Gisl returned to the room, dressed in a white coat like a doctor's, having removed her wine stained clothes and put them in the washing machine.

I fixed the rail and as Gisl was reaching up straightening the curtains her white coat was gaping open revealing her grey pubes, which I watched while she worked.

"Thanks, that's wonderful. What do I owe you?"

"I don't want anything for doing that, err good night."

We walked back to the hall but instead of going to the front door she led me to the lounge, "I've made you a coffee" and pointed to a tray on the table in front of the sofa.

"Oh I need to be going."

"Don't be silly, have your coffee first, silly to waste it. Help yourself to sugar and milk or cream." We sat at opposite ends of the three seater sofa, both a bit diagonal so we were sort of facing each other and chatted. I was distracted by her breasts; they were obviously big and, now without a bra, hung very low but the shape of the bumps was confusing. The additional layer of the coats pockets didn't help. She moved closer to the middle seat so our knees were touching and as she leant forward to reach her coffee her coat was pulled tight and one or two buttons popped open. She sat back against the sofa showing a lot of breast flesh which reminded me of wanting to return to Annette, but I could not keep my eyes off her breasts.

"I really must get going." Desperately wanting to get back to Annette's.

"But you haven't finished your coffee," tapping my knee and pointing to the mug in front of her.

I drained the mug and we replaced them on the tray together. Gisl grabbed my wrist and pulled it to her lap, placing my hand on top of her other hand then sat back again. I tried to pull my hand away "I must be off, it's getting very late."

She gripped harder with both hands "Why don't you tell me what you're really thinking?" Staring directly in my eyes...

"It's late, I need to go." Thinking: 'what I really want to do is go and lose my virginity with your daughter'. I suddenly realised my hand was no longer laying in hers on her lap but had been placed high up on her breast, outside her coat and well above nipple level with both her hands cupping it there.

I pulled away but her grip tightened "você não gosta de meus seios?"

"What?"

"Don't you like my titties?"

"Brincar com eles," and her grip relaxed.

"What?"

"Play with them." Under her guidance I let my hand drop down to cup under her breast and stroked, kneaded and squeezed it. This was my first proper touch of a woman's breast and was now totally turned on. Gisl placed her hands behind her head and arched her back against the low padding of the sofa, pulling the coat tight across her breasts but very wide open. Feeling brave I knelt astride her thighs so I could use both hands and kissed between her breasts. She started breathing heavier, placed her hands on the top of my thighs and turned her head to one side with closed eyes. Then getting really brave, I slipped my hands inside her coat and for the first time ever there was nothing between my hands and a woman's tits.

"Finalmente , jogar mais" The palms of my hands were on her nipples and they felt a lot harder than I expected as I moved over them.

In my innocence I wondered if I dare suck on them and lavish kisses on her chest. All the time I waslooking up at her face to make sure I was doing nothing wrong. I pulled a breast from the confines of the tight coat and lifted my hand off, to make way for my mouth to suck... for the very first time in my life... god was I nervous, my very first nipple to suck on....

I jumped back not expecting metal in my mouth, pulling my hands away, leaving both breasts exposed, I looked. Gisl opened her eyes and turned to look at me, ran her hands up over her breasts and back down again to my knees, "What's the matter, never seen a womans tetas before?"

"Err no, well yes... well no, actually no."

"No?"

"Em no never actually seen real live breasts before and only ever seen one with a ring in a magazine."

"You virgem?" I nodded "Oh wonderful."

"Do these hurt?" Touching the rings.

"Only if they get caught on something, otherwise I don't notice them, I would not have kept them there for 60 years if they hurt.

"60 YEARS! How old are you then?"

"Don't be so shocked, I was brought up in Paris and at the turn of the century they were quite popular for people with money and nourrice, erm nurse. My mama and nurse both had them and I could not wait to get my own. I would play with my nurse's tetas while she fed my younger sisters, but I had to wait till I had breasts. Papa did them in 1917 on my twelfth birthday."

"You're not seventy-two?"

"Two months ago."

"NO?"

She nodded and smiled.

"So these bits of gold were here thirty-eight years before I was born."

"About eight years before you, they're the forth set in these tetas." Holding her breasts up to me.

"Don't they get in the way?"

"No, I have fed my own five children and been a wet nurse to another seven with them in place."

"Wow." I moved forward and sucked on both in turn; she returned to the heavy breathing and sighs.

"Move," patting my legs, "Time for bed." I looked at the clock thinking '2am might be too late to go back to Annette's. I got up off the sofa, Gisl took the tray to the kitchen and met me in the hall, by the front door. "What are you doing?"

"Putting my shoes on."

"Oh no you're not, I will not allow you to leave me in this state," touching her fanny "You're staying here, hoje à noite nós fazer amor."

"What?"

"Tonight we make love."

I suddenly realised the meaning of 'if your allowed to return' in Annette's conversation when I left her. I slipped my shoes off again and followed Gisl to the bedroom; she tossed her coat on the chair and sat on the bed naked. "Come on, we can't make love with your clothes on." She patted the bed beside her and I sat. "Kiss me." I nervously kissed but it felt artificial and cold, she ran her hands all over me and undid my shirt slipping it off my shoulders. "You take off the rest," she stood and walked round the other side of the bed and I took the opportunity to strip and get in bed unseen.

We both laid there waiting for something to happen. After what felt like ages but in reality was probably only thirty seconds I turned towards Gisl. I put a hand on a breast to play with a nipple and ring and moved closer to suck on the other nipple. "That's it come to me, come fuck me." I climbed on top as it seemed the right thing to do, stuck my dick in her and moved it in and out. "That's it, give me a baby." Now the last thing a guy wants to hear on his innaugral shag is any talk of becoming pregnant and her words completely destroyed the moment for me, I went soft and no amount of coaxing changed it.

I woke about 8am to the noise of a dog barking. I went to the loo, grabbed a drink of water and returned to the bedroom for my clothes, intending to leave quietly as she slept. As I bent to pick them up, Gisl threw the covers back patted the bed. It dawned on me how saggy her tits were as they were basically hanging down each side of her ribs, almost to the mattress. "We have some unfinished business," I returned to bed and pretty much the same thing as the night before happened.

I played with her tits while she laid there and I found the only way I could keep them from sagging sideways to the bed was by kneeling with my knees under her arm pits and they sort of formed a big puddle across my legs and her arms and chest. I remembered the old saying 'anything more than a handful is a waste' and realised how true that seemed.

We got up, had some coffee and washed. "Can you do me a favour and run me to Annette's, my car is there?"

We got to Annette's a little after 9am, the smell of bacon greeted us as we entered the back door... "Just in time for your bacon sarnies"

I finished my food and tea, "That was lovely thanks."

"Mama, have you seen the time? You should go or you'll miss church."

Kisses and bye byes all round, "Back door mama."

"I forgot, bye."

"Why not the front door?" I asked.

"It's double locked from the outside with a broken key in it, I have a new lock but I don't know how to get the old one off ."

I looked at it "I'll drill the lock out, luckily I have the tools I need in the car." I got on with it and within twenty minutes I had the door open and the new lock fitted. Annette cleaned while I packed up then we sat at the breakfast bar stools for another drink.

"I take it you weren't allowed out last night then?" with a smirk on her face.

"No I'm sorry."

"Why sorry?"

"I really wanted to come back, I have always liked you, no I'll change that, I've fancied you for a while now and with all the sexy talk I really, really wanted something special to happen between us. Last night was my first time and I felt quite disappointed with how it went." I explained how it had not been a good experience for me and what had happened and my failings.

"I'm not surprised, papa was a dominant man and was in charge of everything, mama was not allowed to 'make love', only let him do what he wanted. Mama told me before we left the party she planned to fuck you last night."

"I like her nipple rings, that was a surprise."

A very nondescript reply "Oh good. What do you want to do now?"

"I have a few things to do at home..."

"I mean what do you want to do about Mama?"

"Erm well nothing. All the time I was there I was thinking of getting back here. I still can't believe I lost my virginity to someone fifty years older than me."

"Why don't you go back there this afternoon, she will be back home about two o'clock and I know she would love to see you again. Oh and she won't be drunk, you are the only man she wanted to fuck since Papa died... sixteen, seventeen months ago. He was her only lover, do me a favour and make her happy, I'm sure it will get better, do it for me please."

"Look I've fancied you for years and sitting here now I'm feeling pretty horny but when I was there I just felt like she is an old woman."

"So you're not into older women?"

"No and to be honest what happened last night has put me off older women."

"Do I turn you on?"

"Oh yes."

"I thought you said you're not into older women."

"No I'm not, but I don't see you as an older woman."

"But I'm more than twice your age," with that smirk again

"No don't be daft?"

"How old do you think I am then?"

"Thirty-five."

Annette stood and hugged my head to her chest and I put my arms round her to hug her closer "Oh Terry I love you for that, I was probably thirty-five when I first met you."

"So you're?"

"Forty-six" we said in unison.

We hugged again and kissed a lovely kiss; my dick got hard. I stood and with my arms round her waist, picked Annette up and sat her on the worktop. She was wearing a very short flared mini skirt, in fact so short her matching coloured big pants were as much on display as the skirt, and a Tshirt. I started lifting the Tshirt and she raised her arms to allow me to remove it. As this was the first bra I had encountered, I fiddled with it to release the clips. Annette removed her hands from my shoulders and cupped her breasts "I hope you are not disappointed with these, especially after Mama's big boobs."

"To be honest, I have always been a boob man and love the look of a nice cleavage, but I may have changed my mind about liking big tits after handling your Mums. They're so big and floppy it was like wrestling jelly, and the dark veins look like a road map. The only good thing about them is the gold rings." I slipped the straps down to her wrists then lifted her hands away, the knot reappeared in my stomach then I saw them fully for the first time. I brought my hands up under her tiny tits and squeezed them gently, avoiding her big dark nipples "Orrh they are divine," bent forward to take one then the other gold ring in my mouth. "I did not expect to see these" and brushed the rings with my thumbs.

"Bit of a family traditon I'm afraid, Grandpapa put them in on my twelfth birthday."

"These are thirty-four years old?"

"The piercings are but this is the third set of rings. Grandpapa put the others in my daughters nipples on their twelfth birthdays so these have been in for eighteen months."

"Did they have a choice? Do they like them?"

"They love them, it's made them popular at school, but no, they had no say in it, Grandpapa was too strong for that but now he's dead, my youngest will chose."

Annette stopped me as I tried to speak.

"Please don't say your sorry, we are not, he was not a nice man."

"Do you think she will have nipple rings?"

"Oh yes, I have no doubts there. When she gets into bed with me she always plays with them and with her sister's too. She wants to know when she'll get hers. She's nowhere near as developed as her sisters were so I doubt it will it be on her twelfth birthday."

I sucked on both nipples again and put my hands under her skirt to pull her pants down but couldn't get to the top under the skirt. Annette let me struggle until I realised the skirt and pants was one single garment then laughed... "Oh your face" and laughed again.

"Now what?" I asked.

"Sadly your leaving, I have friends picking me up at 11." Glance to the clock, "in forty minutes, I need to make myself look good first."

"I think you look good just as you are."

"Terry, keep saying that and I will love you forever but please go see Mama a couple more times, pretty please just for me." Some sad looking eyes and a pout let me know this was a serious request.

"Ok I'll see. If I go should I take a pressie, like chocolates or flowers?"

"Now your talking, she loves carnations, and with that I must chuck you out."

"Reluctantly I go, see you soon and thanks for the breakfast."

"No, thank you for doing my lock, I'll find a way to pay you for that one day," with a wink and smile, "and thanks for going to see Mama."

We stood at the back door, hugged and kissed again. "No'oo... my front door works again you will be the first to use it."

I went home to my attic flat, showered, shaved, dressed and drove to the pub to meet some mates and I told them what had happened. The guy I went to the cinema with the night before knew Annette from when I lived at my foster parents. "Looks like the only way to get in her knickers is to see her Mum. I know what I'd do mate go and fill you boots, if you don't I will."

When I left the pub at 1:30 I purchased some flowers from the farm shop and knocked on Gisl's door. She was again wearing the 'house coat' but clearly with black underwear.

"Hello."

"Hello Terry. I didn't expect to see you, oh are they for me, you didn't need to, Obrigado, entrar entrar, come in."