Coaching Ryans Friend Lisa

Ryan's Friend Lisa Asks for Advice

So that night Lisa watched Tracy spank me seems to have started something.

Of course, it did with me: after being spanked, naked, in front of Lisa, having Tracy finger me also, and then perform in front of them both, it was SO different to see Lisa at rehearsal every week, and every Sunday morning. A "good" different, for sure, part of me likes knowing that Lisa knows how I am, that Tracy shared that part of me with her. And then just the "dang, that's so naughty" part of being that naked and exposed to someone I see all the time, but definitely NOT in that context.

But I think this started something with Lisa, as well. Our friendship continued, and actually we seemed a little closer. I was glad for that; given time to think, perhaps clearly and not while having a lot of drinks with friends, Lisa could have formed a "that was weird" response, and started distancing herself. She didn't, though. The usual bright smile, "Lisa sunshine", so friendly, interactive, loves hugs, and so forth.

What *was* different, was that she asked Tracy to lunch. I heard that it was a great time, and they got to know one another a lot better. Tracy had helped Lisa with her "trivia night" costumes a couple of times, and liked to have Tracy's input on her costume and makeup, and of course I liked that idea of Tracy helping Lisa get dressed. Anyway, those activities had led to some camaraderie, but at this lunch, a whole bunch of things got discussed.

Among them: Lisa liked what Tracy and I showed her, it turned out. Lisa said she got to see a girlfriend she admired "play" with her husband in a way she'd never imagined. And that got her thinking: maybe this would be fun for her? More to the point: how did Ryan and Tracy get to this point? What makes us this playful?

Tracy said she'd help her understand. And she needed to come visit us again.

So that's the story I heard that had led to Lisa's next visit. Again, it was set up to meet for dinner, then hang out and "visit" for a while afterwards. Dinner and drinks, but of course you're interested in the good part, as I was. That's next.

Lisa started off by hugging both of us, and thanking us for being willing to be so open about all this. "Um, sure, you're welcome, but I don't really have much left to hide from you," and that got her smiling. Tracy suggested we get changed into "something more comfortable" to help the discussion, and we did. The girls went to the dressing area and changed into...lingerie, actually, or at least sleepwear. I picked some board shorts that I like to wear around the house. What Lisa had on looked familiar...yes, one of Tracy's.

We talked about this part. What you want is to look tempting to your partner, and whatever you pick should either really sell something you have, or really highlight something your partner wants. Tracy had put Lisa into this pale blue nighty, halter-topped and empire-waisted, with flowing sheer fabric below that, all pixie-faerie hemmed below. With a little darker-blue thong to match. She looked great, I'd never seen Lisa in anything briefer than capris and a knit top, maybe a nice dress at Easter. So yes, WOW, that was an eyeful coming out of the dressing room like that, and it took me a minute to re-calibrate. Tracy was so sexy, she'd picked that yellow bra and boy-short set she bought when I was on the Austin trip, and it looks just killer on her. I felt like a slacker in comparison: unless your girl is into costumes or something, there's not a lot of dress up to do for guys. Tracy is not, and really just likes guys in board shorts or boxers.

Tracy asked, "What did I think?" But before I answered, Tracy told Lisa that everyone here loves each other, wants only the best, and we're bonded. That she's so happy that Ryan can talk about his feelings, and express himself about what's going on, what he likes, and what he wants. If you don't start with that, it's hard to get to the kind of playtime that we have, and showed to Lisa earlier. Got it. Tracy's the same way, btw. Very easy to talk out what is delightful, what isn't , what hurts(!), and so forth.

Well..."Lisa looked great!", I said. And why. "That blue was perfect, really brought out her eyes. And that really highlighted her breasts, you could actually draw it back a little to the sides to show a little more cleavage, but I loved that it didn't hide them, so sheer. Then the sheer fabric at the bottom, just to mid-thigh: I know Lisa fusses about her hips, well if so, the cut of this draws attention elsewhere, her eyes and boobs."

Tracy said, "Really? You sound like a gay fashion reviewer. What do you really think? Tell her!"

Um, ok. "So, first: you rocked me by coming out like that, you're so close to naked and I've never seen you that way. Friggen hot, just that part of seeing you like this, you're all legs, and nice breasts, and blue eyes. Yeah, that looks great on you, it's *blue* and I've teased you so often about how you kill guys when you wear blue" (Lisa giggles). Confirming with Tracy, and giving her a look, "I can say this?" "Yes, go ahead", Tracy confirmed. Okay. I told Lisa, "Sure, it'd be great to pull you onto my lap and ravish you. Just look at you!"

They both laughed at that, Tracy saying that was more like it. If Lisa had ideas of being shy around us, I guess that she'd given up on that...both by coming at all, and then by being willing to play with us again, wearing sheer lingerie around us, and so on.

We all got on the bed, just sitting comfortably.

Lisa asked, "But still: see, that's what I mean. Ryan can just spill about that, it seemed so easy for him, and you encourage him so much to be honest and on the level. Guys aren't like that, usually."

I let Tracy answer.

Tracy told her, "It doesn't happen overnight, and some of it is just him to begin with, he's not an idiot 20-year-old all consumed with the usual bullshit. A big part of it is, we 'claimed' each other at different times as we've bonded, and I'll explain that part, too, in a while. Ryan will tell you that I've 'ruined' him for anyone else; I hope he really believes that, but it's because I've given him anything he's wanted, and he's felt free to encourage me to get anything that I want. And I know your question will be: so how did you get to *that* point, that's really what I asked you in the first place?"

"Geez, it started right away, I guess. We were both coming from places we didn't like so much, with spouses who were mostly consumed with themselves. That got us talking to each other, and that just built and built. And of course it turned to sex chats, phone sex. I wrote him a romantic poem, he would write...well, porn stories about us, as knight and lady, lovers on an island vacation, things like that. What we'd do when alone, secret desires. We just built that, one tale after the next, always being appreciative, coming up with new ideas. And we'd not yet laid a hand on each other. Never even kissed."

Tracy continued, "So it started with all that, and it built a lot of trust. We felt like we could tell each other anything, and largely, we already had. We'd both been hurt, a lot, so we didn't want to say hurtful things to each other, ever. Why would we do that, what would be the point? So from that level, of being able to talk about anything...well...it led to feeling free to do anything, with each other, at least try it out."

"So when we finally got to be together...we had *fun*, lots of it. And made fun of ourselves when anything got awkward. Ryan would tell you...I was too "overwhelming" for him at first, and that didn't matter...I loved watching him whack it, and kept him close, till he got used to seeing all this naked (laughs)."

"We just...learned to trust with this stuff. I thought I had a big butt, he thought it was sensational, and couldn't keep his hands off it. He was concerned he couldn't drill me at first, it was no big deal, OMG could he give mustache rides! And so forth. We just were in love, and well adjusted, and mature about this stuff, having lived through it done badly long enough. It got to be so fun to have pizza and beer nights; Ryan would come over, we'd have sex all kinda ways until about 9pm, then break for dinner, then more sex, then deep sleep. Showers together in the morning, back to work!"

Tracy stopped for a minute, to reposition, and then noticed Lisa. "You know", she said, "if you'd lie on your side, like *this*, and bring that knee forward,*there*, you'll drive Ryan crazy." Lisa, now repositioned, looked tempting indeed. I lay on my side, and tried to make my tummy as small as possible.

Tracy continued. "But we claimed each other; it started with me first, since he was still married. We planned a champagne night, I had a bridal trousseau from before, so I wore that. It was so sweet and sensual, we made love, maybe a bit more thoroughly and tenderly, then he gave me a 'for now' ring and 'claimed me'."

Then I finally got a chance to get a word in. "Yes, I did claim Tracy, it was so freeing to be able to do

something,

about then. I've told Tracy this a number of times, but I think I fully gave myself to her the night she claimed *me*. It was like any other pizza night, but Tracy "made love" to me, like a guy would a girl. She kissed me, took off my shirt, played with and sucked my nipples, caressed me, peeled off my jeans and shorts, gave me a thorough blow job. It was... heavenly... to be part of a whole scripted session like that."

"This was the first time...well, I gave my anal virginity to her. I felt like that, too. She'd played with me there a few times, just touches and pressure, and I responded to her each time. Craving more, as it turned out. All guys don't like it; you do, or don't. No one's indifferent, that I've ever heard of. Guys who enjoy it, a) are blessed, why not enjoy another erogenous zone, and b)really like it. It felt so good when Tracy touched me there, OMG. And Lisa, you'll enjoy this part: I couldn't tell her! She knew, of course, how could she not, by how I acted.

But that night, I was just lying there naked, she'd just finished having my cock in her mouth, and had lotioned my cock and balls. She had her hands on me, and started slipping the fingers of her one hand further between my cheeks. I moved a bit, to let her touch my rosebud, and she teased it a while...all the time, my inner self is begging, 'Please! Take it!'. And she did, like she showed you the other night, only with me on my back. It was exquisite, such a feeling, both the physical stimulation, but the bonding part, too. It's still mostly taboo for straight guys to want this, even now, and I'd just joyfully given my cherry to Tracy. That's how I still look at it, and it bonded me to her."

Tracy smiled at me, and told Lisa. "It was just like that, we were so wrapped up in each other, and I wanted him to feel so special with me. I loved his reaction. But also: he was such a cute guy, and sexy man, and I wanted to fuck him, to see what it feels like when a guy penetrates a girl and 'takes' her. I wanted to 'take' him that way, to make him belong to me, and feel the rush of fucking him. So I did."

Wow, do I love this girl! I gave her a hug, and kissed her. And yes, I'm sure Lisa could see my stiff cock in my shorts, but it wasn't anything she hadn't seen before, we'd crossed that bridge last time.

"Just fingers?", Lisa asked. Tracy and I laughed. "Um, no, you can imagine, right?", Tracy continued, "once I learned he was 'like that', dang I wanted to *really* fuck him, right? Use a toy, or a strap-on, and of course he'd love it." I added, "Oh, very. It opened another whole dimension, a new section of the menu, however you want to call it."

Lisa said, "I think I'm starting to understand. You both were in a place, mentally, to where you could get this started. All those 'pizza nights' sound incredible...just time to explore and try things? You guys had so much fun. Oh, I wanted to ask...um...masturbating? I don't think most guys share that...do you share it, Tracy?"

Tracy answered, "Oh hell yes!" (We all laughed...no filter on this girl!). "Really, from all the phone sex when we were dating, we got very good at it, over the phone. To the point where, when we got together, it seemed like it was easy to show that to each other. Far, far more delightful, in person!"

Lisa said, "Oh, I'm sure. So that's a lot of trust...to be able to have someone just watch you...I wouldn't be sure I was doing it 'right'".

I laughed, "Geez, it hadn't occurred to me that it could be done 'wrong'!"

Lisa was so cute, now being shy. "Well, honestly, I've not tried doing that very often...and...well...I didn't get to the "ending" of it, if you know what I mean. I wasn't sure how it looked. When I watched Ryan the other night, that was the first boy I've watched...probably the first time I've actually watched how it comes out."

We both hugged Lisa. "You're so adorable", I said. "You certainly would want to feel very confident when you showed someone...I get that. The good news is, practicing is actually quite fun! (Laughs). Tracy and I both were pretty accomplished, maybe that's 'unfortunately', since we had partners that really didn't care about our needs. And then we'd had all that phone sex time where 'finishing' was a part of most of those. I know with us, by the time I asked Tracy to perform for me, live, I'd already shown her a couple of dozen times."

I pulled Tracy close, and hugged her. "Can you show Lisa what you did?"

Tracy's not a shy person, but I had sort of put her on the spot. This wasn't like Nicky or Chris, girls she's loved, and who've loved her, and have been naked together. Lisa and Tracy were...really, just friends, and Lisa more my friend than Tracy's. But then, I figured we all wouldn't be lounging around like this if someone weren't going to get naked by evening's end. I'd assumed that would be me, again, being spanked or something for all this delightful naughty talk, but I saw my chance to enjoy Tracy, naked, in front of Lisa.

Tracy turned my head to kiss me, deeply, and then turned me loose. Lisa was fine where she was, but Tracy moved me to sort of cross-wise on the bed, had me lie on my back, and moved to straddle me, on her knees. Mmmm...lioness time!

Tracy leaned forward to kiss me, and kiss my chest, then came back up, drawing her hand across my bulge and lingering there a bit to squeeze me, just because she could, and smiling. Lowering her bra strap on each side, she reached back for the clasp and then removed it, those full, round breasts now freed. She looked great now, in just her boy shorts, and brushed her hair back as she lowered herself onto my bulge. Lap dance time, that's nice, and I don't know if Lisa expected this entire show or not. Anyway, it was a delight, of course I don't get to share Tracy very often, and this first time with someone who wasn't also her lover. Interesting.

Tracy could feel how hard my cock had become, grinding on it as she was. She lifted slightly, putting one hand behind her head, making her breasts display so well, and used the other to begin stroking between her legs. The stroking turned to rubbing, then probing...she was feeling for her clit, through the fabric, I love doing that, too. Found it, you could tell, that little gasp of breath when it's touched purposefully in a session. She looked ravishing, bare chest, strong thighs, those little shorts, that full mane of auburn hair. No one has it like I do. Lisa was mesmerized, maybe only seeing such a show in a movie or something up till now, and of course Tracy is so beautiful like this.

I'd seen this before, of course, but dang this is hot when Tracy performs! She reached inside her shorts now, wanting her fingers right on it. She rubbed, hard, more than I'd try with her, but then she knows exactly what she's feeling. It didn't take much of that, and my baby came for us, so beautiful, so sexy, and then collapsed on me (still straddling my hard cock, and giving it the occasional after-quiver, I love that part too). It took her a minute to catch her breath.

I'm not sure anyone knew what to say after watching; how *do * you restart the conversation? "Any questions?" doesn't sound quite right, "Next!" isn't right either. Thankfully, Lisa started.

"Tracy, that was...incredible! So, um , sexy. I loved that you let me watch you...and Ryan, of course. I could move like that, I think...and straddling your boy, so he can feel you, and you can feel him, would be great, too. You, um, stimulated yourself through your shorts...can you feel it that well?"

Tracy said, "Well, yes. It's right *there* after all!" (touching herself again, and startling a bit, pretty funny).

Lisa nodded..."right, it is there...just start with that, and then...?"

Tracy offered, "You don't have to put all those lap dance moves in...Ryan loves them, so I love doing them. But you can look just as beautiful on your back, or side, or whatever. And that may make it easier to relax, and just enjoy what you're doing."

Then Lisa talked some more, "Oh no, actually the lap dance moves were the best part! At least, a very good part. Can you show me again, maybe slower or something?"

Tracy nodded, then with a sly smile said, "I'll let you rehearse with Ryan. Just straddle his lap to start, of course." Tracy guided Lisa to me, and we both were a little shy, at first by making this level of contact, but of course, the scene had sorta set itself up for something like this. It was fun watching Tracy, still topless and flushed, someone who'd just climaxed a few minutes before, giving guidance to Lisa, all in sheer blue lingerie, now astride my lap and hard cock.

Tracy said, "Just think of those booty-girls in the music videos...they move that way, too. Here, let me help you", and Tracy now straddled my legs, behind Lisa, placing her hips against Lisa's, and put her hand on Lisa's tummy. Now, just move like 'this', see?"

Really? So now I had Lisa on my lap, rubbing my cock, getting flushed and turned on while my topless curvy girl humped her ass. It was quite a scene, alright. Tracy reached lower for a second, and said, "Be sure you're touching him, and you want his cock right on your spot. You'll want to torment him, too, right?" Dayum...she wanted to see Lisa get off this way! Naughty girl, is she perfect or what?

So I reached for Lisa and had her lean down to me, and began stroking her hair, and whispered how great she looked doing this. I kissed her neck and kept her close, it was great to hear her breathing...she was getting there. Tracy now leaned forward a bit, and had Lisa lean back into her, also stroking her hair and nuzzling her neck. She seduces Nicky that way, it's fun to watch, and I loved watching her encourage Lisa this way.

Of course all of us were so turned on at this point, a so-sexy moment with Tracy and I both focused on getting Lisa to climax for us. Lisa was in there, alright, and now so aroused and flushed. Tracy slipped off each shoulder of Lisa's garment while she continued thrusting, freeing her nice rack, and began to caress her breasts. That added just enough, it seemed, because Lisa then leaned forward against my chest, kissing my neck, and grinding hard against my cock, crying out and gripping me as she came. One very hard one, then a couple of softer, shorter compresses, and adorable Lisa was spent.

Then...laughter! Hey Lisa: I think you know how! It was awesome, and we assured Lisa that she looked and sounded wonderful, quite the little porn-star for us. Lisa turned back and kissed Tracy, a pretty good one, and said, "Thanks so much...that was...unexpected...I wasn't planning on going that far". Tracy told her," Maybe not...but I was!". Lisa added, looking at me, "I guess we're a little more close now...we've...um...made contact?" I told Lisa, "Well, yes, I'd say. And I'll just say it, um yeah, you just got off riding my hard cock in a lap dance, I'm even wet from you, so yes: we're pretty close!" That made her laugh, and us too, and we all separated to catch our breath some more.