If I Knew Then... Ch. 04

"However," she said "while I don't want you to stop, this isn't getting us any closer to getting Penny naked in bed with us."

I raised my head and looked at her. "You're serious."

"Uh huh"

"Okay. Any ideas about how to do it?"

She said "We tell her that we have broken up. I tell her that is. I say it is because you fancy her, but that it is ok, and if she wants she can go out with you. You two date a couple of times, seduce her, and then we arrange for me to turn up sometime when you have got her naked."

"Might work, but there are drawbacks. One, I wouldn't get to do this with you for weeks, if not months, because she is pretty tightly buttoned up, and even my charms could be resisted for a while. Two, and more importantly, someone could get hurt here. Most likely Penny. She is only going to get naked with a boy if she is either swept away in passion or has fallen in love. I can't let her fall in love with me just to get her in bed. Not if I love you."

"Hmmn, you are right. And a nice guy, dammit."

"Still, I have another idea." I said. "She fancies Mike. So...."

Tuesday was another bright late winter day, dry but cold in the wind. Owen tried to take the mick in school, and I am sure the fact that Jill and I spent two hours alone in his barn (a well known haunt for young lovers) was well known around school by lunchtime. Which was when I first saw Mike. He was a bit grumpy at first, until I told him of my plan. He bought into it immediately. So at 3.35 I dropped him at the end of his street, and at 3.40 I picked up Jill and Penny. And Jo. Jo was not part of the plan, but, improvisation is so often the key to success.

We spent a fun afternoon at Mike's, playing snooker and drinking coffee. Mike got on well with Penny, and at the end invited her back for another game. Jo accepted the invitation (which had not been to her) and said "Ok. How about tomorrow?"

I dropped the girls home, Jill last, and we had a chance to plot Jo's side-lining, and exchange a kiss or three.

On Wednesday the three girls arrived at Mike's, to find Owen was also there. We naturally split into three pairs, playing a game in the round, Mike picking Penny, of course. By the end of the afternoon Owen had invited Jo to the cinema on Friday. I love it when a plan comes together.

Thursday Jill had chess club. On Friday morning I met Mike, who was grinning. "Kissed her," he said. "She came over and we played two frames, then I walked her to the train station, and she kissed me goodbye on the platform. Meeting her later."

We picked up the girls at the usual spot - just the two of them. Penny got in the back with Mike, Jill in the front with me. Jill leaned over to kiss me hello, and Penny gave Mike a peck on the cheek. We went to Mike's house, and after the first frame they went to make coffee. They were a long time returning, and Penny had that rumpled blushing look I knew so well. Jill and I had taken the opportunity to share a long embrace. "You know it's a bit cold on here," said Jill "Let's have coffee in the living room."

We sat on two sofas, two couples, and chatted form a bit, and then I said something nice to Jill, an she said thank you, and kissed me, and then began to kiss me more, and Penny and Mike took up the cue, so we ended up all four of us snogging in our pairs. Until Mike's mother arrived home.

Saturday was already well planned. The four of us on a trip to the Aquarium, back via Penny's house for the girls to change, then off to a party at Charlotte's. All day we stole kisses and hugs and walked hand in hand, and once Jill whispered in my ear that she wanted to do what she was doing last week, right now. But there was no way to arrange that.

To be honest I was pretty frustrated too. So when Jill and Penny came down the stairs from Penny's bedroom I had a hard job not wolf whistling at them or ravishing her. Penny was pretty in her black dress and chiffon shawl, and I suspected stockings and suspenders as well as her high heels. But Jill was a vision in her long dark blue skirt and embroidered blouse, her hair curled and waved, light make-up and a gold chain necklace that dipped invitingly between her breasts.

We had special permission to be out to midnight, but didn't want to waste a minute.

Charlotte lived on a farm. It was her eighteenth and she had a barn dance. It was actually quite fun, with a caller and people showing us what to do, a huge buffet and both beer and cider in barrels. And there were nooks and places out of the way where a couple could discretely enjoy a private moment or two. Getting undressed was out of the question, but I discovered in a shady corner that beneath her skirt Jill was wearing stockings too. "Penny leant them to me," she whispered as she opened her thighs and I slipped my hand over the smooth skin above the edge of the nylon hose.

"She helped me put them on," she continued, as my fingers found her panties "It was rather erotic actually, just the two of us in our underwear with her kneeling in front of me doing up my clips."

"Hmm, sounds it. Wish I could have seen that."

"I saw she was putting them on and said to her that I had never worn them, so she offered to lend me a pair, and the belt. And when I said they felt naughty, that I felt very exposed and that if you tried putting your hand up there wouldn't it all be a bit risqué she just giggled and said that was the idea."

"Penny has a notion then." I said.

"Well I asked her if that was what she was planning for Mike tonight, and she said she might let him put his hand up to find the tops on the outside but not the inside of her thigh."

"Mike will be pleased, but not as pleased as me" I said, pulling her pants aside to play with her fluffy lips and mound, and slip a finger tip onto her clitoris.

"Oh but you should have seen her" Jill said "She has such pretty underwear, all matching in black lace, all sort of see through, when she stood up after fixing my straps she was just a foot away, and I could see her nipples through the material, all hard, thinking about Mike feeling her thighs, I really wanted to touch them, and let my hands feel her stocking tops, and slip inside her lacy panties, oh god your fingers are so good in me, oh I wish it was your cock" She covered my mouth with hers, and thrust her hips in a counter rhythm to my hand.

"Oh Sean, I love you, I want you to do this to me every day, make me come Sean, you are going to make me come."

All this was conducted in quiet whispers, although Jill's orgasm was powerful enough that she could not restrain herself from a slightly noisy gasp, but no one was close enough to notice.

We kissed and cuddled while she recovered, and she whispered to me "Can we leave the others home early, I want you so much, and we could stop the car at the forest park near Penny's"

I groaned with frustration at the idea. "I wish, I wish, beautiful woman, but it is nearly eleven now, we are going to have to go in about fifteen minutes at most anyway."

"Tomorrow then. After lunch?" she said, eagerly.

But on the way home plans changed. When we dropped off Penny she announced that her parents would be away for the afternoon, and suggested we all went to her place. I recognised that this was in fact a thinly disguised request to give Mike a lift, but is suited us well enough, as long as Jill and I for some time to ourselves.

We got a report and briefed Mike on the way home. Jill was full of advice, and I of course had a wealth of knowledge about Penny that I couldn't explain but was useful in suggesting strategy to him. Steady progress was being made. He had indeed been allowed to discover the pleasurable junction of flesh and stocking on her thigh, and had been allowed a hand on the inside of Penny's knee. Fully clothed light pressure on the breast had also been permitted (or at least not objected to). We thought that with a little persuasion by example, things might progress further quite quickly.

Jill was next to drop off, since she had the midnight curfew. I walked her to the door at 11.54 precisely, and as we approached her mother opened it. (Not that she was sitting looking at the clock and watching for us or anything.) She invited me in for a cup of coffee for the road, but I said no thanks, as I had Mike to get home as well. So on the doorstep, with her mother watching, Jill said "Thank you Sean, that was a lovely evening," and she kissed me on the cheek.

I stammered goodnight, and went off blushing.

In the car Mike and I discussed plans. At home I masturbated three times before I could sleep.

I collected Jill first on Sunday. She kissed me on the lips, three times, in the car, on their front drive. I didn't struggle too much, but did say "After the look she gave me last night I hope your mum didn't see that."

Jill laughed and sat back and said "We had a long talk last night. Mum was a bit scandalised that I kissed your cheek in front of her, and started into telling me not to lead you on, and boys can't control themselves and how it wasn't fair for me to tempt you. So I told her straight out, I'm over eighteen, I'm not stupid, and nor are you. I told her we kiss, on the lips, and I like it and I'm not going to stop doing it."

"I bet that went down well."

"Better than you might imagine." Jill said, "She went quiet for a bit, and then said 'Sorry.'"

I nearly crashed the car on the bend I was taking. "What!"

"She said 'Sorry. I'm sorry Jill, I just worry about you. I forget.' and then she said 'I was eighteen when I met your dad, you know. We saw each other at a couple of dances, and then he was away for a month at TA camp, and I didn't realise how much I missed seeing him until he came back. After that he was the only boy I dated, and we were married two years later, a week after he graduated. Of course it was different in those days. I had half a dozen boys who I went out with on different dates, all at the same time. Nowadays you tend to have a single boyfriend at a time. I'm not sure that is such a good thing. It could all get so intense so quickly. And of course in my day we didn't have The Pill."

I was driving on a straight this time, but nearly crashed again. "She said that!"

Jill was perfectly calm, and said "Yes. And she went on to say that she supposed I didn't want to get married before University, and getting a career, and that she couldn't really expect me not to want to be intimate with a boyfriend. But she did say that she thought it was important that I didn't rush into things, or allow myself to be pressured, either by a boy or by talk among the girls. She said if I did ever sleep with a boy it should be for love. It would be a boy I wanted to marry, even if it was before we married."

"Bloody hell." I exclaimed "So what did you say."

"I told her that I thought she was right. And I promised her that when I decided I was going to do it for the first time it would only be with a man I'd marry."

"Well you can't say fairer than that."

"Well I could have said it in the past tense... Or said that when I do it this afternoon it will be with a man I want to marry."

"Unless you get to do it with a girl." I said

"Ooooh, naughty. Anyway I don't think that is on for today. Actually I'm not sure we can really do it together today, unless we leave early in the car."

"Well, we'll see. Let's not rush it though. I still worry about hurting her. I think Penny could have a really good time, but it will be a big thing for her."

"And for us." Jill said, and softly squeezed my knee.

Mike was in good form, and bearing a bottle of Chablis. We had two bottles, a red and a white, both burgundy.

Penny was in a blouse and a long gypsy skirt, voluminous and soft, which I knew would allow a fair amount of fully clothed fumbling, if she allowed it. Getting her to let go was the trick. It was clear pretty soon that Penny had no plan further than us turning up and that she had dinner organised. So we sat on the sofas, and made small talk until Jill made some excuse to kiss me. Then I made an excuse to kiss her back. Then Penny kissed Mike, and conversation ended.

Kissing is fun. Deep, exploratory, open lipped and mouthed, tongue entwined kissing (known alternately as 'French kissing' or 'snogging') is fun. Snogging and cuddling and getting comfy on a sofa, lying down facing each other or with one or the other on top, legs entwined, hands roving over fully clothed bodies, is fun. If it is your first time at that sort of thing (or maybe your second or third) you can do it for hours and not get bored. But if you are used to a greater level of intimacy, a lesser level of clothing, a deeper level of penetration, it is still fun, and not exactly boring, but it does become frustrating and almost annoying not to be able to move on to more daring and exciting things.

Still, while Jill and I did whisper occasionally about our more advanced desires for each other, we did enjoy the next hour of leisurely kissing, and the voyeuristic aspect of the arrangement was quite exciting.

Jill and I were on one sofa, Mike and Penny on the other. They were arranged in an 'L' shape, and each couple had ended up with feet pointing to the angle. Surreptitious glances showed us that Penny was lying on top of Mike, and he had raised one knee between hers, which meant that her legs were open inside her skirt, and her pubis would be pressing against his thigh. Mike's hands were sometimes on her bottom, pressing her against him, as she rocked her hips in the oldest dance of all, and sometimes his hand was up on her blouse, cupping her breast. Penny was starting to get breathless, her movements becoming less discrete, more vigorous, less controlled.

Jill whispered to me "Penny's getting hot, shall we take the lead?"

I said "Yes," and shifted so that Jill could sit straddling me. She sat up over me, and raised her skirt, so I got a brief flash of her underwear before she settled down, her panty clad pussy against my trouser covered cock. She was wearing the stockings again. She rode me then to orgasm, her gasps and grunts echoed by Penny, who I noticed glanced our way several times. Jill tried to time it so that she did not get too far ahead of Penny, and didn't make that much noise. Mike was really not sure what to do, since he had never had a girl do this on him before, but he coped. Eventually I heard Penny's voice change. Her in breaths became slightly whistled "ooh" sounds, and rose in pitch. I knew she was very close, and I saw her raise herself on her hands to force her pussy back against Mike's thigh. Her bottom was bobbing up and down, and her face was flushed and full of astonished, puzzled pleasure, her eyes wide, as she stared down at Mike, who was smiling at her and had reached up with both hands to hold her breasts, supporting her and stimulating her.

Jill was sitting upright now, rocking her pussy back and forth against me, her breathing also becoming tight and staccato. Then she came, and fell forward on me, and I raised a knee between her legs so she had something to clamp between her thighs, and continue to rub herself against. Her skirt fell down my raised leg, exposing her stockinged thighs and her bottom, which I grasped as she bucked against me.

Across the way Penny had finally let go, her breathing stopping after a final "Ooh" and then with a sudden thrashing of her hips to grind herself against him, she threw her head back and cried out "Oh, Oh Mike, Oh goodness, oh Oh" and then made a high pitched noise, as her head snapped forward, her mouth and eyes three perfect circles, her entire body still.

I knew what would happen next. She said "Oh" in a soft low voice, and collapsed on Mike, with great heaving breaths.

Jill had been lying with her head on my chest, watching this happen. I had been nuzzling her hair, pretending not to be watching as well, not that Penny or Mike would have noticed in any case. Now Jill came up to kiss me again, and whispered in my ear "That was beautiful. I think that was her first. You lie still here with me for a moment, when she recovers she might need a chat with me."

We nuzzled and kissed a little more, and Penny and Mike did the same, but after a few minutes more Penny pushed up on Mike's chest, and said, "I'm really sorry, and but I have to go to the loo." Jill laughed, which made Penny look round, embarrassed, until she said "Me too. You can have the upstairs bathroom."

The two girls left us, grinning on the sofas.

Mike and I chatted, for a moment or two. He had enjoyed that, and wanted more. "She said that she had never come before. She liked it. She kissed me really differently after it. Sort of softer, but hotter. Do you think she'll do it again?"

I laughed. "Oh yes." I suggested we break out a chablis, and we went to the kitchen. The downstairs loo was empty, and I could hear the girls voices upstairs, there was a certain amount of giggling.

They rejoined us some minutes later, and were pleased to take a glass of chilled white, and curl up with us on our sofas as before, but there was a distinct change in them - they were wearing tee-shirts now, not blouses, and it took less than a second to realise that Jill was not wearing a bra. I was pretty certain Penny wasn't either.

My theory seemed to be working out. In a previous life I had picked Penny, not Jill, at the party three weeks before. I had been clueless, she had been cautious, we had very slowly moved towards a full sex life, as each of grew in confidence and we overcame shyness and religious upbringings. This time I didn't have those problems, and realised that Penny, who once she had tried and enjoyed a new expensive was always eager to do it again, was at heart much more hedonistic and sexually liberated than she appeared. If I had been confident enough and paced things better, not rushing her but not giving her time to over-think things and get guilt ridden, and if there had been an adventurous couple to lead us on (because as I only discovered years later, Penny was strongly voyeuristic with a big exhibitionist streak) I might easily have been able to get her to orgasm within the first week of first kissing her, and have got her bra off too, instead of taking weeks and months to achieve as much. I was almost a bit jealous of Mike. Ok, in another life Penny and I had shared a foursome with Mike and his girlfriend Tara, and we had swapped before, so seeing him snog Penny was not new. But to know that he was the first boy in this life to feel her breasts, and to make her come, and that she had taken her bra off for him, even if it was at my girlfriend's instigation, and I had suggested it to her to do...

I knew what we had planned, what we discussed. I knew Mike would be the one to suck her nipples first, and to finger her first, and to lick her out first, and his would be the first cock Penny would hold, wank, lick and suck, have come in her mouth and rub on her tits. In this life Mike, not I, would take her maidenhead, although the plan was that I would be there to watch. And of course, I would be there with Jill, taking her right alongside Penny. Which was wonderful, but still, I felt proprietorial, jealous. I wanted to be the first to have Penny. I had never realised how strong that urge was.

In part it was a bit of a noble urge. I felt that Penny, who I had once loved deeply, deserved to remember her first time with affection, as having been with a boy who loved her. Even though I was setting her up for Mike's seduction, and I could see that he was fond of her, I felt bad about that. But then again, she was eighteen, horny, willing, desperate to throw off the repression of her upbringing, along with her clothes, and would I was sure she would be just as happy and active a bisexual swinger in this life as she became in our previous one. Just a bit sooner. So I had to admit that the larger part of my jealousy was probably just greed and redirected feelings of failure. It took me months to do what Mike had done in days. Was I really that bad at it? That unattractive that she had not orgasmed with me? But then again, Mike had the advantage of my briefings. Ah, if only I had known then what I know now....