Surprised by a Friend of the Family Ch. 02

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Another Surprise: A bachelor weekend is better than anticipated
5.8k words
4.64
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Part 2 of the 2 part series

Updated 10/20/2022
Created 06/28/2013
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Kevin1974
Kevin1974
16 Followers

Chapter 02: Another Surprise

This is a continuation (Ch. 2) of

"What?", said Darla, interrupting my broad grin.

I had a little adrenaline rush, but then blurted out, "Just people blabbing about how bad the mall crowds are today. What did they expect?" I went to the bathroom a little later and responded, "my schedule is clear ;-)". Delete thread.

The long holiday weekend came to an end and the workdays passed, but it was hard to concentrate. Jenny had played into so many fantasies over the last two months I was struggling with a little mania. I had so many ideas that I wanted to test, and nearly all of them could be humiliating for me, or even cause trouble. But every time I started to reign in my imagination I was reminded that she reached out to me, not the other way around.

Finally, on that Thursday evening I received a follow-up text, "I've got a surprise. I'll come by at 8pm tomorrow, okay?" Darla and Susan were catching a train earlier that afternoon at 3pm.

I put all concerns and reservation aside and simply replied, "you bet."

I probably started pacing a full 15 minutes before she said she'd arrive. I dressed casually, but with a collared shirt, in case she wanted to go elsewhere. I opened a bottle of wine and was well into my second glass when I heard a knock at the door. Carrying my glass, I opened the door and saw two smiling faces.

Jenny greeted me with "Hello John (big smile), this is Lauren."

Lauren was almost identical in her physique to Jenny: somewhat athletic, curvy but firm, and light brown hair below her shoulders. Both were dressed a little oddly for early December in Maryland - medium skirts and sparkly, sleeveless tops. They were also about the same height of maybe 5'8" or 5'9".

I stepped aside and said only, "Welcome." I took a deep breath and regained composure.

Lauren entered first, lifted the glass from my hand and started to look around as Jenny lingered just inside the door. As I closed the door, Jenny looked into my eyes and then moved closer, and as she closed her eyes she said, "Play along okay?" and planted a very, emotional kiss - not gentle but certainly not sloppy or exaggerated.

I didn't want to or have to think. "Okay!" I said with moderated enthusiasm.

I followed Jenny into the kitchen where Lauren waited. I could now see Lauren's eyes and a really pleasant smile, and her top revealed more than I noticed at the door. I was navigating this with a little caution and stayed well out of arm's reach from Lauren. Ignoring my open bottle on the counter, she had opened another bottle of wine from her bag. She spun around and then returned, handing a half-full glass to each of us before returning to pour her own.

Jenny explained, "Lauren is a very special friend, and we were talking on the night after her birthday. She just turned 22 and was telling me about her plans and her goals, and one special curiosity."

I turned to look at Lauren who maintained a very broad but somehow shy smile as she glance back and forth between Jenny and me.

Jenny continued, "I immediately thought of you, and realized that I've not been very good about keeping in touch with you. All in all, this seemed like a very appropriate time to reconnect. But! I've got a errand to run, and I'll let Lauren explain!" With that, she put down her glass after only one sip and reached for her keys. "I'll be back!" she said with a big, enthusiastic smile, pivoted and walked toward the door.

Lauren and I watched her walk away, and as she reached the door, Lauren said only, "By sweetie" and then turned to me. Still outside of arms reach she said, "So John, I am sorry to spring this on you, and this is waaaaay outside my norm, but Jenny insisted."

I was playing along with anticipation, and turned to make sustained eye contact. "I'm all ears."

"Well that's just it," she said, "I need a combination of things, and a good listener is right at the top of the list. Jenny said you would be. Let's go back to the kitchen."

I was a little deflated, hoping this wasn't about something legal, or money, or worse, a breakup story. But I tilted my head, trying to seem caring but not paternalistic, "I'm glad to help."

We got to the kitchen table and I sat a friendly but respectful distance, perpendicular to her. "Well!," she began, but taking a big breath to gain composure. "I was telling Jenny, that I'm now 22, and while I absolutely adore her, I have never been with a man and wasn't even sure how to talk to a man about this." She looked down, and there was a sustained pause.

Then she fidgeted a little - a false start - so I interrupted. "You certainly have my curiosity, and I already have lots of questions, but if it's a listener you want, I'll wait for you to invite my questions."

She blushed a little, but quickly replied, "See that's exactly how we came to be here. Jenny said that I could think or talk through this with you out loud, and there wouldn't be any games or big assumptions. I need to ask you something as a man, but not as a date, or a prospective boyfriend or something more. Is that all right?"

My ego deflated again, but I mustered, "Of course. I'm very non-judgmental - tell me anything you wish and ask me anything you want." Quietly, however, I feared the worst. Jenny ran off on some errand and I'm stuck here giving advice to her friend on how to pick up a guy.

But then she looked over and just stared at me, directly into my eyes. I didn't know if she was going to tell me about a crime, or about a business proposal, or what.

After almost 10 or 12 loooong seconds of staring, she suddenly moved closer and said, "I think this is appropriate first," and she leaned even closer, lifting her chin to kiss me.

I kissed back without aggression, but certainly aimed to express curiosity. It was, after all, a very authentic feeling at the time. We kissed for nearly a half-minute and I re-oriented my expectations yet again.

She lessened the intensity of the kiss and soon after pulled back just enough until our faces were only 18 inches apart. "Okay, so I turned 22 two weeks ago. And I've never been with a man. Jenny told me about her night with you, and it sound amazing."

I think she sensed my unease at the revelation of something I needed to keep secret, because she continued with new energy. "Oh please, please know I'm entering into this secret you share. I want to be part of it. I think I need exactly what you shared with her. I need someone mature, someone intelligent, and someone big enough and masculine enough to make me feel like a woman. The kiss was a little test to see if I could tell you all this."

She paused and I looked back and forth between her green eyes. I offered, "If you've talked this through with Jenny, and you understand and respect my need for secrecy, and I guess recognize that this probably can't evolve beyond a shared curiosity, I think I'd like to know more. But that secret could hurt a lot of people." I was still bothered about Jenny's revelation but I was also sensing something extraordinary might be happening.

Here rounded face broke into a big smile. The she leaned forward to kiss me again.

After a few minutes of much more exploratory and suggestive kissing, she asked, "Is there a place we can go be more comfortable than here in the kitchen?"

"We can go to the TV room, or I have a daybed in my den?"

"Perfect", she said as she reached for her wine glass, "please show me."

I led her down the hallway to my den. I had already set the mood anticipating that if things had gone well with Jenny, it might be less presumptive than leading her to the guest bedroom.

We got inside the room and I grabbed for the mouse of my desktop machine and started some music. The light from the monitor was just enough to see all that was going on but with a little ambience.

We started kissing again. She removed her arms from around me and I soon discovered that she was unbuttoning her blouse.

"Here let me," I said, wanting to give the full treatment I assumed she was seeking. As I finished the last button and reached inside her blouse, I was surprised to discover she was wearing a camisole without or instead of a bra. The silkiness made for a new level of adventure and excitement as I explored her curves.

Meanwhile she had started unbuttoning my shirt from the bottom up. When she got to where my arms were in the way, I pulled my shirt up and over my head, exposing my grey t-shirt. We pivoted and I pulled her gently down onto the daybed.

I interrupted the kissing and reached down to untie her shoes. As I move to the second shoe I saw what was in store. "Do you know Jenny through swimming? I can't get over how similar your physique is, so athletic but so feminine."

"I was her team mentor in her first semester. You're not the first person to comment on the similarities but please know that I love the comparison."

"Well I agree that you should both be flattered." For a split second I thought about unbuttoning her pants next but remembered the "first time" motif of this adventure, and remembered the importance of setting a pace. Instead I sat back down and kissed her, maybe a little awkwardly, as I removed my shoes and socks.

When finished with my socks I pulled her gently lengthwise along the daybed. I kissed her provocatively, but gently, another minute or two before saying, "Lauren, you get to set the pace. If I'm moving too fast, or too slow, you get as much control as you want."

She pulled back and looked at me, "What if I want you to be totally in control?"

"I can do that," I said with a smile and comfortable authority, and went back to kissing.

I imagined what it was like to be 20-something again, and I felt her curves through her silky underclothes. As my hands moved downward I pressed on her ass to drive her into my crotch, my hip, or my leg, anything to simulate what I hoped she was thinking was inevitable, but also looking for clues from her response.

I rolled her onto her back and began caressing her through her jeans, and that's when I became fully assured of all that was possible. Her, "Oh John" was what I needed to hear to progress toward unbuttoning her jeans. I started with one button and then a second, but I could tell I would need to unbutton the third and last to get my hand in there. As I finished the last button she surprised me by lifting herself from the bed and using both hands to remove her own jeans. This was going to be good.

================

She could tell from my positioning that I had unbuttoned my own pants and she reached up to beat me to the zipper. She pulled it down and rolled the pants of one hip while I did the other. I managed the rest as gracefully as possible and soon I was in t-shirt and boxers as she was in her dark green silky camisole and matching panties.

We may have established that I would be in control, but at this point she took charge of the pace. She rolled my 6-foot, 210 pound frame onto my back and she laid on top, not breaking the kiss. She positioned herself so she could gently grind against me, and by that time I was rock hard.

I was lost in all that was happening, and maybe not paying close attention to the kissing, because suddenly she lifted her head away from me. Looking down into my eyes she maintained the rocking motion and seemed to be communicating in some non-verbal way that accompanied our physical intimacy. I reached under her camisole for the first time and it was magnificent. Round and firm and full in my hand - I had to see them, and I told her. I started but she took over and lifted the silky green covering over her head and shook her hair so that it cascaded mostly over her right shoulder. I was in heaven.

I had the strongest urge to feel her against my chest and I lifted myself into a half sit-up and pulled my t-short above my head, tossed it, and in the same motion pulled her back to me and kissed her further. It was an image I've revisited a hundred times since.

I gently rolled her on the narrow bedding so that she was mostly on her back and I could now kiss, lick, and gently blow across those wonderful nipples while exploring those panties with my left hand. Her breathing and gentle moans affirmed that my pacing was on target.

I traced the edge of her panties along her opposite (tight) thigh, and then gently stroked he soft inner thigh. As I moved upward along the panty line of her left thigh I curved by finger underneath to create some anticipation. I similarly but more assertively then ran my upper index finger entirely underneath her upper panty line along her belly and she squirmed a little. I then moved down to massage her vulva through her panties and when I paused at the base of her mons she really came alive and kissed me firmly. I focused now on her clitoris through her panties and she was visibly and audibly excited. She reached for me and massaged me through my boxers but wasted almost no time reaching into the front of my boxers to free me.

I took this as a clue to pick up the pace when suddenly with her other hand she took mine and pulled her panties to the side and put my finger immediately upon her clitoris. I moved it slowly and lightly at first, and then picked up speed but without additional pressure. She was squirming and licking and blowing my ear and neck. The she said, "You've got to lick me; please lick me now. Will you do that?"

"Of course" I said, and she was already removing her panties. There was enough light to make out a narrow, carefully groomed racing stripe that guided me to where I needed to be. I planted a kiss at the top, and then progressed along the length of her labia. I returned with a gentle lick to the top, and then a second in the same direction, and then a third but this time pressing in to part the lips and taste her. She moaned and grabbed my head at the same time, admittedly providing a little assurance, as there was plenty of evidence that even if she had not experienced this before with a man, she may have enjoyed the more knowing touch of a woman.

I alternated between gentle flicks, tickling licks, and playful sucking of her clitoris, with occasional probing invasions into her vagina. At some point she drew her knees upward and I put my hands on the extraordinarily soft, creamy thighs, and broke free to kiss the inside of her thighs. I was surprised with a "No!, No! Please don't stop." I quickly returned and that began a crescendo toward her first orgasm. It was though she had just slipped into a hot tub - she simply melted and every muscle relaxed.

I paused but did not remove my mouth from her vulva. Avoiding her clitoris, I continued my gentle kisses and now ventured from thigh to thigh. As she began to stir again I returned to her lips and moved again to her clitoris, with only a gentle kiss at first. As I sensed she might be ready, I increased the gentle licking and when she responded more strongly, I did too. She came again within seconds, and this time she clamped against my head and was vocal and loud with a series of "Oh!'s". I had to work hard to stay in contact as clearly she was lost in her pleasure and was bucking her hips.

When she relaxed she was breathing heavy and I was too, partly from the strain but also from the excitement. She pulled under my arms and I kissed my way up to her mouth again. I was hard between her curvy belly and my abdomen.

Her kissing was gentle and dream-like initially, but then turned very passionate and assertive. I was supporting most of my weight on my elbows and forearms and I could tell by her movements she wanted to roll me onto my side. As I did she maneuvered above me and I could now tell she wanted to completely reverse our earlier position. I laid flattened on my back and she came down on top. But as she did she eased herself right into position to engulf my cock. I wasn't sure if it was planned or unplanned. It seemed like she aimed it that way, but then her nearly instantaneous reaction of gasps and spasms and then vocalizations told me that something had surprised her.

I let her go but focused on control. Like Jenny, Lauren was the personification of fertility. The curvy hips and curvy bosom were the sort that would turn guys' heads, even if they weren't the sort you'd see on a magazine cover. She calmed down after just a minute.

"Hey", I said gently, "I don't trust myself in there without some birth control. This is too much of a fantasy come true to control myself."

"I brought condoms, but I didn't intend for that to happen really. I wanted to feel what it was like and ignored the urge to be cautious, but I also wanted to taste myself, so give me a minute." She then put both hands on my chest and lifted herself, then maneuvered down and took my cock in her mouth. No light kissing or gentle licking, just straight down into almost fully engulfing it.

She cupped my balls and I knew what was next. "I'm going to come Lauren." But she reacted only by sucking more earnestly and I exploded inside her mouth. It felt like I shot three or full streams, and my consciousness faded a little with each. I actually fell asleep or maybe passed out.

I truly don't know if 10 minutes had passed or a whole hour, but I became reoriented there in my office and felt the warmth of her body next to me under a blanket just barely big enough to cover the two of us. Her breathing told me she too was asleep, and I kissed her forehead as I used my left hand to reach around to further explore her wonderfully full hips and ass.

She came to slowly, and eventually whispered, "That was pretty amazing."

"I think so too," I replied. She started stroking me and the contact made me erect almost immediately. The nap was like a reset button.

"I'm going to get a condom, is that okay?"

"Of course," I replied. without standing up completely, she took a few steps to the other side of the rug in my small office and reached in her bag. She began opening the package as she returned.

"Can we start again he way we did earlier, with me on top? That totally caught me by surprise and I want to do that again."

"Yes, come here," I said as I guided her with both hands on her hips. She straddled my legs, and began to unroll the condom down the still hard shaft. When she reached the base she moved one knee forward then the other and sat right back down with me inside her. The warmth of her in the otherwise slightly chilly room was amazing, and it seemed to magnify the connection between us. Until a few hours earlier, this was a stranger that might have caught my eye in a coffee shop, but nothing like this would ever have been likely if not for the accelerated introduction by Jenny.

Kevin1974
Kevin1974
16 Followers
12