7 comments/ 43363 views/ 10 favorites Surprised by a Friend of the Family By: Kevin1974 I've always found my wife's friend Susan attractive. She is now in her late 50's, and I had known her for about the last 15. She is smart and funny, a little extroverted, and physically you might describe her as uncomplicatedly feminine: no noticeable makeup, petite but a little curvy; and with wavy, medium-length graying hair and blue eyes, magnified by little round glasses. As my wife's best friend, she was comfortably out of bounds for me, but I certainly enjoyed her visits and she played into my fantasies regularly. Her husband Alex was a similarly bright guy, a little older, and much more aloof than any of the rest of us. It's almost as though Susan was his interpreter, and it was very unlikely that we'd see him socially if Susan wasn't part of the group. Susan and Alex lived about 20 blocks away. Susan and my wife Darla usually met at a coffee house midway, but frequently visited each other while running out errands when they didn't go on such adventures together. Sometimes Susan would stop by our house before Darla returned from work, and I enjoyed every minute. They also traveled out of town together, usually on train rides to New York or occasionally to the mountains. Alex and I were usually invited to the mountains, but the New York trips were strictly girls' weekends. We don't have kids, but Susan and Alex have a son and daughter that always went on trips to the mountains, but when they became teenagers we saw them less often. About three months ago Susan and Darla went on one of their weekend trips to New York. On that Friday I dropped them at Union Station at about 4pm and waved them off from the train station waiting area. I didn't plan anything for the first night -- preferring to just eat, drink and watch what I wanted, and then go to sleep when I wanted. I somehow got motivated to redo my office, and had just finished vacuuming when there was a knock on the door. When I opened, there was Jenny, Susan's daughter. She walked right past me saying, "I'm pissed that my mom and Darla wouldn't include me on their girl's weekend and didn't want to sit around the house so I came over to make you dinner." I don't think I managed to say anything for the first 30 seconds; I just followed along behind her into the kitchen. Jenny was always an interesting kid. She didn't get in trouble like her older brother Chris, but always seemed to be a challenge. She transferred to a special school, but despite being very bright, didn't want much to do with school. She dropped out at the end of 9th grade with a perfect GPA, but had to wait six months until she was 16 to complete her GED and enroll in the community college. But by the time her age peers were graduating, she had completed two years of college and was set to begin her sophomore year at a nearby university, again with a 4.0 GPA. She had a mixed confidence: she had a strong value system and was extremely confident of her intuition and ability, but extraordinarily reserved. "Shy" isn't the right word; she didn't care enough to engage others unless they made her angry. As a younger teen she had matured early, and always wore very baggy clothes. She was also always pale, and had a rough time with acne, so I imagine that she simply worked within her strengths and chose not to seek social and fashionable venues that would have been important to many other teenage girls. But this night Jenny was looking and behaving very different. She wore a blouse that matched her eyes, which I hadn't really noticed before, and tighter fitting pants. Her blouse was unbuttoned and showing just a hint of cleavage. I was nearly finished with a beer and kind of put it to the side, when she said, "Don't open another, I brought a bottle of wine from my parents' fridge to share with you." I probably had my mouth open, not sure what to say, when she suddenly stopped, looked up at me and said, "Don't worry John, this will be fun. I'm a good cook!" I just nodded okay while babbling some affirmation. As she unpacked her grocery bag I could see it was going to be some sort of crepes and was playing along with curiosity. I was also absorbing this young woman that I had really never noticed before. She was also very chatty, which was probably the most unusual thing about this encounter. I could tell a lot of this new Jenny was because of feeling excluded from being part of something she had been looking forward to: the New York trips. I was little surprised at how familiar she seemed in our kitchen, and after an initial effort to help I decided it was better to stay out of the way and watch. But just as she pulled a large saucepan down from the hanging rack, she looked my way and caught me staring at her chest. I quickly looked away as she just blurted out a curious, "Huh!" and she broke into a condemning smile, I went to open the wine to avoid confrontation and blushing openly. The planned dinner was prepared with short-order cook efficiency and it seemed we were eating within 20 minutes of her arrival. We talked about all sorts of things, and the conversation flowed, jumped, hopped, and returned. She was very good company, and for someone well over twice her age, I held my own in keeping her engaged. She had been sitting in the chair next to me rather than across from me while eating. She got up to get the wine bottle and offered to pour more in my glass. As she did I noticed an extra button on her blouse had been unbuttoned. This time she caught me and there was no escape. I simply said, "Sorry, this is a very different evening than I had planned and both surprising and enjoyable. " "I'm enjoying this too," she replied, "and I hope it wasn't too to awkward the way I barged in." She continued, "I was unraveled earlier when I saw that they were already gone without even responding to my asking to join them, and I was even crying on the way over here. When I got to your door I took a deep breath and just decided to entertain you while I entertained myself, and forget about them." "Well you're doing very well," I said. We can download a movie or just keep talking. She let out a modest, maybe practiced, two-syllable giggle and led me to the living room. She sat next to me on the couch and the conversation wandered into new areas. She talked about boyfriends and disappointments, and even a suspenseful story in which one of her older brother Chris's friends, with whom she had a casual relationship, suddenly came up to her room and began forcing her into an uncomfortable situation when Chris was hosting a drug binge in their home. It ended without trouble but served as a wakeup call about her relationship with her brother. Perhaps to switch gears or lighten the conversation, she asked me about my early relationships. I told her about the big ones of a year or more, the often-embarrassing outcomes, and the heartbreaks. I talked about the way I, as a representative of many guys, stumbled through the combination of physical and emotional intimacy, and how there was not only no one to prepare me for that, like most guys I didn't really have anyone with whom I would have wanted to talk about it. "Well, tell me about the physical part. And how you learned about those things," Jenny asked. I didn't delay, "I think in my first two relationships, I was matched with someone similarly inexperienced. It was often embarrassing with lots of important questions unasked and unanswered, but in both cases things clicked and we found routines that were good for both of us. But it was very much amateur hour, and although I might have worried about it back then, I look back on that time verrrrry fondly." "Later, in my 20's," I continued, "I met a woman who was about seven years older who had me figured out early. She just told me what to do, and it worked, so I listened and learned. Her name was Analia, and I knew she carried around a lot of emotional baggage, but I think that made me care about her even more. Because we were in different places in our lives, and I later learned that I was a rebound relationship for her, things went well. It was like an extended summer romance, where you knew it would someday end but both decided to fully enjoy it while it lasted. But things deteriorated when she had to be away for two semesters for her residency, and we had trouble renewing things at the same enjoyable level. We both had little flings with others, and neither of us had enough interest to put everything back together." I had been talking about that relationship for over 20 minutes, and kind of staring forward rather than making a lot of eye contact. When I looked over at Jenny, who at this time was sitting just inches away, her eyes were kind of dreamy and focused on my lips. I know I gave it a brief thought, but when she sensed my hesitation she smiled, looked me in the eyes, and said, "Do you think you can get me and my car home safely?" Ice broken, yes, but there would be no mess to worry about. We cleaned up a little, went outside and I drove her car to her street, parked a few houses up, exchanged thanks and knowing smiles, and then I walked over to the 7-Eleven where I knew there were always cabs available. My phone vibrated around 8am. I had already been through the newspaper and was about to start my plan for the day. It was a text from Darla with an abbreviated update, "Having fun, stayed out late after a show and only now getting rolling this morning. XO." But there was also another, earlier text there from Jenny, "Woke up feeling much better -- thanks for excellent company and cheering me up. I'm bringing you sushi tonight. Resistance is futile." ================ I think I stood there for a whole minute, thinking and re-reading the text a few times. I guess I was a little worried, maybe a little responsible or even guilty; but I also reminded myself that it was entirely fascinating and I could (and she could) put the brakes on at any time. I sent a reply with a smiling wink, and suggested 8pm, just after dark. I was pretty industrious for the next seven or eight hours, so I didn't have an opportunity to think through it much further. I knew it might be crossing a line - until now all the initiative had been hers - but I thought it would be a complementary gesture to have some chilled sake to acknowledge her sushi idea. I got home around 6pm, showered and dressed comfortably but presentable (collared shirt and heavy cotton pants) and then turned on the news. Jenny sent a text around 7:30pm that said, "I over-planned and the sushi carryout is ready already -- can I come over early?" I replied with a quick, "You bet" and then scrambled to get some place settings together and to find a sake vase, cups and other things like bamboo placemats, fancier chopsticks, plates and dipping bowls. She was really only 10 minutes early but was apologetic, and I quickly dismissed her concern. Besides, when she stepped inside I saw that I wasn't going to wait for her to slyly unbutton another button. Tonight's blouse revealed curves I didn't even know she had. It was like her breasts were ski jumps pointing 60 degrees apart. The rest of Jenny was curvy too, but she had a relatively narrow waist. Even though she had been to the restaurant, her hair was still a little damp from an earlier shower, and her shampoo was like a gentle perfume that was just enough to be distracting. I snapped out of my momentary trance when she asked where I should put the food. "On the counter," I offered, "and we'll move it from the carryout containers to a nicer setting." The sake and settings were a hit, and I'm sure it made her efforts seem even more appreciated and comfortable. Jenny took in everything, spun around, looked at me, clenching her teeth under an involuntary smile, and I readied for a spontaneous hug or maybe more. Instead, she just said, although with enthusiasm, "This is going to be so fun!" I was a little relieved and a little disappointed. I was looking for a physical connection but admit I wasn't necessarily ready for the possibilities. Dinner and talking was fun and easy, and sitting across from me in the small table allowed me many opportunities to notice the details. Then, at one point, she seemed to shift gears and said, "John, what did your girlfriend Analia teach you exactly?" I looked up with a little urgency but she continued, "I've seen porn and I've had boyfriends, but I just haven't had someone to ask before." I opened my mouth to start talking, broke into a shy smile, but decided to be open. "You can probably guess it was mostly about foreplay and oral sex. But it was also about talking and being honest about what you want and what you like. I guess it's normal to want someone to think you're naturally gifted, but I think you later discover that it's even more erotic to know that it's a shared, intimate exploration." She was all ears. "It wasn't so difficult for me to explain what I wanted or liked, but I'll admit that I learned a lot from her," I continued, and I think that helped a lot with our otherwise unbalanced relationship. She made more money, was way ahead of me in graduate studies, and had seen much more of the world. Most importantly, I think it was important to her at the time to be in control of the relationship." "You didn't mind?" she asked, "Didn't you worry about being the dominant one?" "Not at all. It was great in every respect. I also knew somehow that it wasn't permanent, so even if I had been older or more established, I'm not sure I would have had a reason to care." "Well tell me what she looked like," asked Jenny, "Was she pretty?" I knew I'd want to tread carefully here. No matter what came of this evening, I know Jenny was developing or establishing a new identity and sense of self in these conversations. "Analia was certainly girl-next-door pretty," I offered. "Her hair was a rich brown and so were here eyes. That may have been especially attractive after having a difficult breakup with my earlier girlfriend Katy, who was an artificial blonde with blue eyes. Analia was also curvier; she was a swimmer when she was younger, and as she got older she developed a very feminine shape." "Huh. How do you think an old boyfriend would describe me?" Jenny asked. "Obviously you heard things about Analia that you have in common. Except for your green eyes and lighter brown hair, I'd probably describe you pretty similarly. You have similar curves and a similar bone structure, but...". She disrupted my hesitation with a more evocative, "Buuuutttt?" "You are, well, a good bit firmer than Analia was at 29." She persisted, "Which do you prefer?" "Hmm. I don't know how to explain it exactly, but as I got older, I began to appreciate the way women get older too. I know you don't see older women modeling swimsuits and lingerie too often, but there's something very exciting about seeing someone of any age feeling or being sexy." Jenny shuffled in her seat. "Now," I went on, "some of those feelings may be due, in part, to the notion that as I get older it is increasingly unlikely that I'd have those kinds of experiences with women your age. And I know you caught me looking again today, but I really couldn't help it. I don't really ever even get to be around women your age." She was blushing a little and smiling, so I elaborated. "You know, when I opened the door and saw you I didn't know what to think, but I was 100% curious. As we talked , I didn't really process it, but I was having a really great time. And it was surprisingly easy to ignore the larger context of how we know each other. So when I caught a little glimpse here and there of that creamy white skin, I couldn't help but try to catch another." "Do you want to see them?" She was looking straight into my eyes. I inhaled. She expanded, "I want to show them to you." I shook my head mockingly, while saying, "You bet." She stood up, unbuttoned one button and then looked at me. Locking eyes, she reached down and pulled her blouse over her head. I was expecting a simple two-second flash, long enough for me to say something approving. Still looking directly at my eyes, she reached behind and unhooked her too-small blue bra. She paused, smiled, and then rolled her left shoulder and the strap fell to her elbow. Holding the bra in place with her two hands, she repeated the shoulder roll on her right. "You've done that before", I said with a smile. "In front of a mirror a few times, including last night," she confided with a smile. I read into these little comments other rehearsing: Jenny not only rehearsed the bra removal, but the discussion we were having. Then she ceremonially dropped the bra and stood there with unblemished curves that I had never seen even when I was younger. I slowly stood up from the couch. "I think I'm supposed to say something like 'awesome' or 'magnificent', and I guess both are appropriate. They're so perfectly, beautifully, creamy white." I was at risk of babbling further. She didn't ask if I wanted to touch them; instead, she said, "I want you to touch them," and she moved to me. I cupped the outside curves at first, then sliding both underneath each breast, and then back to the outside. Leaving my left hand in place I traced the top curve from the top down to her nipple. This was a curve I had dreamed of but never seen. "Sit," she said, and I did. Jenny then straddled my hips and enveloped my face with her breasts, but only for a second. "Sorry," she said, " I always wanted to do that and I guess I should have asked, or at least played up to that. I keep worrying that you're going to stop me." "Do we need to talk about any of this? Why it's happening, or what might come of it?" I was looking up at her now, and she was looking down at me between her two beautiful nipples. She leaned back a little and I could see she was thinking. "Is it curiosity, experimentation? There's probably no wrong answer if we talk about it." I was concerned for her, of course, but I was also worried I might blow this. "Last night was really fun, and nice," she said, "and tonight has been even nicer. I am curious, and experimenting, and it feels kinda safe even if no one else would understand or approve of me being over here. The secretively makes it more intense. This is kind of embarrassing, and I don't want to freak you out, and it's only been like 26 hours, but I haven't been with a friend like this, male or female, talking this openly. It's like I've been daydreaming and thinking and wondering about all sorts of things for years, and suddenly I have this chance to play them out. But I think that's it. As much as I like you (smiling), I'm not going to steal you from Darla." With that, I moved in gracefully but buried my face again and began kissing the inside of her right breast, moving toward her nipple, and then gently licking and inhaling to create a rush of air surrounding it. It was instantly erect, so I sucked it gently, briefly, and moved to the inside of her other breast. She seemed a little lost when I next looked up, but then lowered herself down until our faces were even, and she kissed me, almost little roughly. We kissed for a while before she eventually reached down and lifted my shirt and undershirt over my head together. She then pressed herself firmly against me and went back to kissing. After a short while I began kissing her neck and she started to spasm mildly. She was worked up, and suddenly stuck her tongue in my ear. It was wet, sloppy and noisy, but I enjoyed knowing I was working her. When she paused I maneuvered around and gently nibbled her earlobe. I exhaled gently across her ear, sucked on her earlobe and then inhaled slowly as I did with her nipple earlier. The rush of cool air on her wet earlobe, the sounds in her ear, all as she pressed against my chest with hers and squirmed on my lap, she began spasming again. At 20, and based on what she told me just earlier, I don't know if she ever had an orgasm with another person. I didn't want to embarrass her or worse, make her suddenly self-conscious. Orgasm or not, she was loving it and I was too. Surprised by a Friend of the Family Ch. 02 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. Surprised by a Friend of the Family Ch. 02 As she rocked gently back and forth in dream-like trance, she suddenly pulled the blanket up behind her and over her shoulders, and then laid down on top of me. She straightened her legs alongside mine and then started to tremble. Then the rocking motion became more deliberate and then with her cries it became almost aggressive. Her excitement was creating the same for me. She began cumming forcefully, almost convulsively, and then collapsed completely on top of me. I didn't cum and was still inside her, but in her peacefulness and the warmth of her body I drifted in and out of consciousness with her. I woke first with the feeling of being forced out of her as my erection faded. I saw itt was now 10:15pm, and I began to wonder about Jenny. Lauren awakened as I held her and I said, "Hey there," to which she let a deep, happy sigh and rested her head again on my upper chest and should, with her nose and mouth tucked in against my neck." It's after 10:15," I continued, "Do you think we need to be worried about Jenny?" "She'll be back at 11," Lauren answered, " I suppose we could get showered up." "Do we now have secrets to keep from Lauren? Would she react badly about this tonight? Things went further than they did with her." I suspected some of this was choreographed between them, but maybe not all of it. "Oh no, she knew my intentions and she'd probably be disappointed that she missed an evening with you if nothing happened between you and me. I think she's begun counting on more regular trips for Darla and Susan to New York...But we should get a shower. Can we do it together?" "Of course. The guest bathroom shower is huge with double shower heads. Let's go!" I said with new energy. ==================== My goal was to be showered and dressed and back to talking in the kitchen by the time Jenny returned, but I knew I had enough time to enjoy the shower. Lauren was very clingy as we went into to the guest bathroom next door and as I started the showers, twice stopping to kiss. Clearly this had been both an intimate and emotional experience for her - and me too - so I wasn't going to spoil it. For at least the next 45 minutes, she would have my full attention and affection. As we walked into the shower she picked the opposite shower head and wet her head and warmed up, so I did the same under the nearby shower head. I could have stayed there watching her from two feet away all night, but when she looked up at me I moved in closer. She also stepped forward and now the water was warming her back rather than hitting the top of her head. We had a prolonged wet and slippery kiss. I didn't get to cum in our second round, so I was getting hard again, but I wasn't going to be assertive and overdo it on her and our first encounter. Besides, this was plenty nice. It seemed like only a few minutes before we were startled by a knock and then Jenny's voice, "Lauren, are you in there?" I could tell by the change in volume and improving clarity that she was entering the bathroom within the space of that short question. Lauren quickly maneuvered to the opening of the walk-in shower and stuck her head out, "I'm in here but I'm not alone." I then heard Jenny say, "Good!" and then there was some muted talking and whispering between the two. I imagined Lauren was sharing details or answering Jenny's questions, but I was not prepared for all that happened next. Lauren came back into the warm water and said, "I told her tonight was awesome and perfect." But then suddenly Jenny appeared, naked and ready to join the shower. Our shower is plenty roomy, but I'll bet the previous owners did not design it with this in mind. Jenny wrapped her arms around me and looked up to say, "I hope you don't think I took you for granted, but I had a feeling you would be just what my Lauren needed." She then removed her left arm and encircled Lauren and drew her in close to us, and the two began a very affectionate kiss. I had no idea what to make of all this, but they could probably tell from my erection that I was optimistic. Jenny and Lauren began giggling and broke the kiss, and then Jenny turned to me and said, "John, I think we should work together to give Lauren the best, soapy scrubbing of her lifetime. I smiled and reached for the bar of soap under each of the shower heads and handed one to Jenny. I pivoted Lauren around to have her back to me as Jenny knelt down and began washing her feet. I supported Lauren with my arms underneath both shoulders and lathered up the bar of soap in front of her. "Hold this," I said as I gave her the soap and began focusing on her wonderful breasts and belly. Meanwhile my erection was pressing against her butt cheeks and only getting harder. She pressed back against it with a very subtle rhythm. Jenny was working up her legs as I washed each breast for a second and third round as I kissed her neck at the same time. "Okay, spin around," command Jenny. Now I was holding Lauren in my arms in a familiar and fun position and she looked up into my eyes. She smiled and then lifted her chin to kiss me. I reached for the soap to my left and lathered up her back but hastily advanced to her butt. As I massaged her cheeks she pressed against me. At 5'8", both of these women were only four inches shorter than me, so when Lauren reached down to grab my erection and point it downward, it comfortably slid between her lips without requiring any special maneuvering or discomfort from me. While it would have been impossible to get inside her without lifting at least one leg, this was certainly enjoyable. About this time, Jenny made her way back up Lauren's legs and was now focusing on Lauren's behind. She must have seen what was happening between Laurens thighs because suddenly both Lauren and I straightened up. There was a hand cupping my balls and based on Lauren's startled reaction, there was a finger inside somewhere. Lauren was almost paralyzed, and in pleasure, and when I saw a small bottle of either hair conditioner or body lotion next to Jenny on the floor of the shower, I surmised that the finger might actually be in Lauren's now-lubricated ass. The hand left my balls and then Lauren showed an even more startled reaction and her eyes seemed to roll up into her eyelids. I guessed Jenny now had at least one finger from her other hand in Lauren's pussy. Lauren was lost, and I was probably now supporting 60% of her weight in my arms. Jenny knew what she was doing. Suddenly Lauren started breathing with exhaustion and relaxation, and Jenny stood up to appear behind her, forming a Lauren sandwich. Lauren was still recovering as Jenny looked into my eyes and revealed a big smile. "My turn!" she announced. Lauren suddenly came to, reached around Jenny and kissed her passionately. As Jenny embraced Lauren I moved around to be behind Jenny, mimicking the fun I had moments ago supporting Lauren, and I was just as hard as I was earlier. Lauren kept Jenny occupied and I focused on soaping every inch of Jenny. I could access the sides of her breasts but not much of the rest, so within just a minute or so I was already progressing down to her legs. I tried to imagine how Jenny treated Lauren's feet and ankles, then calves and thighs. I started with soap and finished each part with a massage. As I lathered her full, rounded ass I had an inspiration and hurriedly rinsed the soap away. I then stuck my nose and tongue forward as I pulled her hips slightly toward me to access her pussy. Jenny accommodated me by spreading her feet wider, apparently without breaking her kiss. The angle wasn't best, and I wasn't feeling effective, so when I noticed the small bottle I decided to mimic Jenny's success with Lauren earlier. The bottle was actually a lube, and Jenny must have brought it. I put a big squirt of the clear goop on my index finger and pressed against the little puckered hole, noticing that Jenny was making this very easy. The stuff worked, and my index finger slid right in. I decide to take it one step further with a second finger, and that interrupted the kiss! I paused until she recovered but then followed with my left hand, putting that index finger into her vagina and then curled it forward to find the little rough patch on the front wall of her vagina. She responded with what seemed to be a momentary loss of control, and two-part spasm. I kept the fingers of my right hand in place but really worked my index finger in her vagina, with the "come here" motion as rapidly as I could without cramping my forearm. Lauren had tightened her grip on Jenny because Jenny's knees seemed to have given out. It was amazing to watch all this from my kneeling and crouching position. As Jenny did earlier, I stood up to make to match Lauren and sandwich Jenny, kissing her neck but then leaning in to kiss Lauren on the mouth, all while holding Jenny firmly in place between us. Jenny's head was on Lauren's shoulder and she seemed to be whispering in her ear. Lauren looked up at me and with a grin she came around behind me. Now I was in the middle and all three of us were facing in the same direction. With the shower heads warming us from both sides, Jenny leaned forward to put her hands on the wall, and Lauren reached around to grab for my cock. She squeezed it firmly as she stroked it, and I almost didn't notice Jenny reach downward. She had squeezed another glob of lube into her hand and spread it between her ass cheeks. Suddenly her hand joined Lauren's and they together guided my dick straight into Jenny's ass. Both Jenny and I let out a moan, and Lauren reached forward even further to grab for Lauren's hips. Jenny held me still for a short while, but then gave in to Lauren who started guiding the humping as I had my very first experience with anal sex. It was different than I expected. The lube made everything slippery but it still seemed tighter. Jenny had only one hand on the wall and seemed to be masturbating herself while I developed a rhythm with Lauren's added emphasis. Jenny arched her back and turned to look at me. "Kiss her!" Lauren commanded. I did. Then Jenny said, "Will you come inside me? Please?" And it was though I was waiting for permission, because I lost it then. This was an unusually intense experience, and I regained composure as I heard Lauren giggling, but also little interruptions of "oh my god," realizing she had just witnessed something profound. As I slipped out, Jenny stood up and spun around and kissed me first, then Lauren. I think we all said something exclamatory, all at the same time. I stepped back to lean against the shower wall. As I opened my arms both girls leaned in on each side of me and we held on to each other there. Jenny then excused herself saying, "wait here" and then jumped out of the shower. I soaped up quickly but within a few seconds Lauren was enveloping me with both arms. "I want this to happen again sometime; if you're cool with it, I know Jenny will be too." I kissed her, suddenly a little mixed up in how I fit in to all this. In the beginning I saw myself as a convenient and safe contributor, but now I was somehow invested. I knew I could reign that in and control it, but for the next few minutes I was going to pretend I was still in my early twenties and all this was part of a possible future. After a few minutes, Jenny returned all dry but eager to be under the warm spray with us again. It seemed unfair that one man should have all four of these beautiful breasts and two wonderfully rounded asses to himself, but I wasn't being asked to share. But when Jenny and Lauren began kissing again, it was clear that while I thought they were sharing me, they were actually sharing each other with me. And I wasn't bothered at all. ===================== Surprised by a Friend of the Family She was catching her breath when she suddenly jumped off and announced, "I've got something else to show you." With a single button, a zip, and a downward sweep, her pants were coming off her ankles, She had a matching blue thong, positioned just perfectly on her hips. "Wow." That's all I could say. ==== "Will you strip down to your boxers?" I didn't hesitate, stood up, and removed both pants and socks. She then gently guided, almost pushing, until I landed back on the couch. She was just inches from me falling toward the couch and straddled my lap again. "I like that your underwear matches," I said. "It may not always be easy, but I think every guy probably likes that." She responded by sitting firmly on my cock, planting her lips and mine, and started to grind. She was really getting worked up now and when I began kissing her neck she started to spasm again but now she was gently crying too. I knew what was happening with more certainty now, but she was in charge and I was just letting her ride. As she calmed down, I spun to the side and laid back along the couch lengthwise. She hovered over me and her full breasts were hanging with almost no sag, and they were simply irresistible. I was kneading, almost support her body weight with my two hands on those beautiful, white, firm double handfuls and she resumed grinding. Suddenly she collapsed, almost as though she passed out. I just held her there for minutes, maybe even ten. I may have dozed off briefly with her as I fell into a trance from the rhythm of her breathing. Eventually she sat up and began to reach down to reach inside my boxers. I watched her hand as she pulled my cock free from the front opening. I was hoping she'd play with her mouth, but instead she climbed back over me and moved up and down as my naked cock moved along the now dampened crotch of her thong. She was not so lost this time. Instead she was staring into my eyes, no smile, just a stare. Suddenly she sat up, still staring, reached down and pulled her thong to the side and repeated the motion. This time my cock was glistening as it glided across and just within her outer and then inner labia. Her once-rhythmic motion became erratic, and this time she was really losing it. I was part-spectator, part inanimate object of pleasure. I was very tempted to use a well-timed thrust to sink my cock inside, or at least make a move to "suggest" it, but I waited to see what happened. Obviously, she was enjoying being in control. Suddenly she lowered herself on top of me and let out a sustained moan. Her upper body was collapsed upon my chest but her hips were spasming. Then she straightened her legs outward and straight, with her clitoris still pressed against the outer end of my cock, and that seemed to renew the intensity. I was mesmerized and fascinated, and I still can't believe I didn't come. I wondered if I might then reach down and guide myself inside her, or if she might. Instead, she just seemed to turn off. She fainted or passed out, I don't know if there's a difference. I was listening to her breathing for almost a whole minute when she started to regain consciousness. She lifted her head a little and said, Oh man," and then collapsed again on my chest. She raised up again and looked into my eyes and said, "I'm so sorry -- I was selfish -- well I'm not sure I was even thinking about what was happening. But I'm sorry you haven't come yet after I've just had a parade of orgasms. That has never happened to me, even with my mom's vibrator." "I have enjoyed every second, so don't worry about me. I loved being part of it, but someday I'd like to watch you with that vibrator; I'm sure that would be a show." She didn't say anything, but slid down my dick as it rode along her stomach, then between her breasts, then to the side of her chin and right into her mouth. No nibbling or kissing or licking or blowing; she just completely swallowed it. She may have gone up and down three or four times before I felt that inevitability, and I didn't even think to warn her. But as she sensed it coming she picked up the pace and then went the whole way down and began swallowing. I might have wondered, but I truly did not want to know how she learned that or practiced it. I settled for being rewarded by her ability and desire. Suddenly I was the one losing consciousness. I was drowsy in a way that seemed beyond my control. She came up and kissed me and curled into my left side, with her left leg over my abdomen, and that's all I remembered. I had not noticed the time earlier, so when I woke up I was surprised to see that it was just after 2am. She was sleeping deeply. I reached down to pull up a blanket, realized I was hard beneath her leg, but must have fallen back asleep almost immediately. When I woke up again it was after 3am, and I worried this would be a problem for her. She was awakened by what must have seemed anxious behaviors, and she just said, "Hi." "Hey, we might have a little problem" I said, "It's later than what is probably acceptable for you to arrive home without lots of questioning. It's after 3am." Really?", she asked, but not with alarm. "It will be okay, but I should probably go now." She got up first, and I took another good look at her naked. She didn't have a belly, so despite her curves above and below, you wouldn't call her rubenesque. Instead she was like the paintings I remember of Andromeda, with broad hips, a large and broad but firm chest, and yet the abdominal muscles of an athlete. I got up after just about 10 or 15 seconds and dressed fast enough to be caught up to her and finished together. By now we had both come out of the fog of sleep and I reached out to grab her hand. She turned her head, and I said, "Okay now, come sit with me for just a minute. This was fun and it's probably not so good to have a night like this come to an end in a rush. But let me tell you that no matter what range of thinking or emotions you go through, I'm willing to talk about anything and everything. If you go home and sleep and wake up unworried or unbothered, or who knows, unimpressed by the whole thing, that's all okay too. But you must promise that you won't let any bad feelings swirl around too long behind those bright green eyes." She looked at me with a sincere, almost incredulous look, and I worried. But before I could raise a question she broke into a smile, and said, "If you worry that I will have a single regret, you must be insane." Then she planted a big, firm kiss on me that push me back on the bed. "But I really should go now." We had had very little to drink, now more than six hours ago, so I wasn't at all worried about her driving two miles home. But I was still a little worried about what she would be thinking when she woke up the next day. Jenny texted me when she got home and that was enough to allow for a deep, anxiety-free sleep. I awoke the next morning and after a little reconstruction knew I had not dreamed all this, and then realized that I may be daydreaming about it for the next few decades. At 4pm I drove to the train station to retrieve Darla and Susan. They were chatty the whole way home and then Darla asked, "How will you manage with Jenny?" I looked up into the rearview mirror with alarm as Darla then leaned over to tell me in mock confidence that Jenny was disappointed to not be along. "I sent her a text with our travel details and she texted me back saying she's looking forward to my return," Susan answered. "I called her and suggested that may she can join us on a trip another time, maybe after her graduation next Spring, but she replied, 'Oh, we'll have plenty of time together; it's okay for you to enjoy your time with friends whenever you want. I can keep myself busy.'" "She's really grown up." Darla said.