Surprised by a Friend of the Family

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.