Stephanie and Her Friends

So, I dropped Tammy off at Brooke's place. I had walked her to the door, and Steph met us. She gave me a really loving look, kissed me quickly on the lips, said "Thanks, baby. You did good, I know it. Talk to you later", and went back into the house.

I didn't have much else to do Sunday. Took the Z/28 out for a run out into the hills west of town. Enjoyed the breeze. Stopped at a burger joint, then went home. Did some chores around the house. Thought a lot about the girls, and particularly Stephanie. She told me she is really starting to like me, and Tammy said the she told her she loved me. This is not good. She's way too young to have feelings like that for a guy my age, and probably for any guy. She just hasn't been around enough. It's not going to be good at all if she gets too attached to me. She needs to be able to move on and have relationships with boys, or men closer to her own age.

Around 6, my neighbors, a couple around 35 or so, saw that I was in the back yard, so they invited me over to drink some Paso Robles zinfandels, and eat some red meat. I could not refuse. Enjoyed the time with them chatting about life, vacations, stories about coworkers and friends. The phone in my pocket was silent all night until about 10 minutes before I said good night and it buzzed. I had a message. I excused myself, said it was late, and left to get back to the house.

Went in the house around 10PM, and turned on the laptop which booted up while I went to the bathroom to empty the bladder. When I was back the computer was up, and I opened up g-mail.

Steph's message was there: "Hey, old fart. You there?"

Next message, time stamped 5 minutes later:" Guess not"

Then five minutes later: "Really would like to talk to you. I'll be on for a while, mail me when you get a chance."

I sent a reply, "Hi baby, I'm here. What can I do for you?"

"I really need to talk to you, but I can't from home. Anyone could hear me. I need to meet you for that date I was talking about. OK?"

"Sure. Can you tell me what's bothering you?"

"Yeah, sort of. Tammy told us all about what you guys did last night and I am really jealous. I feel like I should be doing all that with you, but I know I can't or shouldn't because I'm a virgin, and you're so much older, but my pussy really tingles when I think about what you were doing with Tammy and with Lane."

"Tammy said that you told her that you loved me. Is that the problem?"

"Oh, god, she wasn't supposed to tell you. I just blurted it out once, I'm sorry, I didn't really mean it."

"No it's OK. I think we really need to talk, because the way you are feeling, we need to understand each other a lot better. I really never want to hurt you in any way, but I can see the way this is going that there could be trouble."

"You're not going to dump me are you?"

"No way, baby, you're special to me. We just need to work this out carefully, OK?"

"OK. I trust you, but sometimes it's hard to."

"Yeah, I know. So when can we get together to talk?"

"Well, tomorrow, I work in the morning from 10 to 1, then I have a class at 2 until 4. I think the best time would be after 4. I can meet you at the Starbucks, would that work?. You've been there at that time before, so should it be OK tomorrow?"

"Yes, Steph, I can be there at 4. We can take our coffees, and go for a walk. Is that good?"

"Yup, that will work."

"You really did tell Tammy that you loved me?"

"And you put your finger up her butt?"

"So she really did tell you everything?"

"Ooohhh, yes she did. She said it was the best time she's ever had, and that's why I'm so upset and jealous."

"We'll talk about all of that tomorrow."

"Yes. About loving you, I'm not sure how I really feel about you. You know I told you before about us girls, and how I love them like sisters, and would do anything to make them happy. Well I really feel the same way about you. I don't think I love you in the romantic, I want to marry you and spend the rest of my life with you, and have your babies kind of love, but I'm getting really attached to you, you're special to me, don't know how else to say it."

"Steph, I am so flattered by all that. All I can tell you is I feel the same way, and we need to talk this through and understand how we go forward from here. Are you good with that?"

"Yeah, OK."

"See you tomorrow?"

"Yup"

"Good night, love."

"Good night, love"

And there it was. This was going to be tricky to work through. I had my work cut out for me to help her deal with this.

I closed down, went to bed, and thought not about Steph, but about the great time I had with Tammy, and I replayed a couple of the scenes in my mind, with my dick.

Next day went by pretty quickly. I wasn't expecting any messages or calls from Steph or the other girls, and didn't get any.

I finished up work about 3:30, and wandered out to Starbuck's. Got there about quarter to, and got my iced coffee and sat in the corner, started up the iPad, and read about the DNC in Charlotte. Had to chuckle at the rhetoric. Democrats!!!! Though, based on his speech, I could be tempted to vote for Clinton, but just a sec, he's not running.

I didn't even see her come in. I looked up and she was already sitting in the chair on the other side of the small bistro table. "Hey, there. Still smiley?" This was getting to be her standard greeting, and I loved it.

"Yeah, always smiley.... get you a coffee?'

"I'll get it. I do have my own money you know" she said very flirtatiously.

She got up, and went to the bar. About 5 minutes later she was back. "You want to talk here, or should we go?"

"Let's go."

As we got up, her left hand fell into my right, and we walked out the door.

The area was on the fringes of downtown, so it wasn't all concrete and glass, there were smaller buildings, some open space, a neighborhood park or two. There was a small green belt around a stream that fed into the big pond in the park by the community college campus.

We walked toward the green space by the stream. We didn't say much. She told me a little about her part-time job, her classes. I told her about my job, told her that I did have to travel once in a while, so could be gone for up to a week at a time, not often but sometimes.

We got to the green space and wandered down the path until we found a bench under a tree, a ways off the path. It was fairly secluded.

"So, Steph, talk to me, tell me how you feel."

"Its pretty much like I said. I feel close to you just like I feel close to the girls. I call it love, but maybe that's not the right word, I just don't know. You've been so wonderfully kind and understanding and considerate. I mean, you are pretty much the perfect guy."

"OK. I'm totally flattered by how you feel about me. And I can say I pretty much feel the same way about you. But we need to understand I'm, what, 24 years older than you. I'll bet your dad is younger than me."

"Yeah, you'd win that bet"

"So you do understand that there really is no long term future for us. I don't think we could really fall in love, or get married, and have babies, just like you said, but, I think we could be really good, special friends. I'd like to be able to be kind of a, god I don't know the right words. I'd like you to be able to talk to me about anything. I can help you understand boys, and what you are going to run into as you move along. You can ask me about situations you run into, problems you have."

"I have my four, well actually five friends, you haven't met Abby yet. Would it be OK if you kind of become one of our group. I mean it will be weird, it's all girls, and you're a guy, but then you've already fucked two of them, so I guess you've already passed the initiation, if you know what I mean." Big smile on her face.

"Look, whatever works for you guys, and I'll be honest with you, the sex with Lane and Tammy was really good."

"That's what bugs me. I want to experience that too, but I'm a virgin, and I always had in my mind to hold out and have sex the first time with a boy I really cared about, that I loved."

She stopped suddenly, I think realizing what it was that she had uttered.

A very pregnant pause ensued and then she said, "Oh, god, I've just told you that I want to have sex with you."

"Yes you did."

A moment or two passed, and then she said, "OK. I think that's the right thing to do, but I can't do it right now. I mean, somehow, I need to work up to it. I can't just bend over the bench here and have you stick it in me."

"Oh, Steph, I'd never do that. First time should be really special, and if you want to go ahead and do it, then I will do everything I can to make it as special and memorable as I can possibly do."

She dropped her head on my shoulder, put her arms around my chest and just squeezed really hard. I could feel her sob a little.

"Hey, I need to think about this seriously, and maybe talk to Lane and Tammy. Would you be OK with that?"

"If you trust them, then so do I. Let's get back. Do you need a ride somewhere?. My car is about two blocks from Starbucks."

"My car is back on campus, so you can drop me there."

We walked, we drove, I stopped, she left, and I was dizzy. This was so far outside of my comfort zone, but I cared for her so much, because of her honesty, and naiveté, her youth, and so much the promises of her future,

Monday night passed with no contact. I didn't really expect anything after the bombshells from the afternoon.

Tuesday went by the same way.

Wednesday afternoon just after 4, I got a call from our receptionist, saying that a Ms Pearson is on the line regarding her project for her business course.

Ah, yes, the luscious Ms Pearson, a.k.a. Kelly. I took the call, and said, "Good afternoon, Ms Pearson. How can I help you on this fine day?"

"I need to do a follow-up interview with you to expand on some issues that I discovered when I analyzed your responses from our previous interview."

"My schedule is fairly open, so I think it should be pretty easy to find time to meet."

"Can I come by your office again? What time would be convenient?" she said in her most adult, professional sounding voice.

"Anytime, you can come over now if you like."

"I thought so, what time is your office open 'til?"

"The doors stay open until the last person leaves, but most are gone by 5"

"OK -- I'll be there by then."

At about 10 of 5, Teri called to tell me I have a visitor. I went down the hall, and Kelly was there, again dressed very professionally business like for a student. Skirt a couple of inches above the knee, light blue blouse, with a light sweater over the top.

She followed me back to my office, sat in the side chair opposite my desk, with her back to the open door. The first thing she did was undo a couple of buttons of her blouse, so I could see a couple of inches of her frilly, powder blue matching bra. There was also a very nice expanse of cleavage visible.

"Be sure to tell me if anyone is coming this way, OK?"

"No problem. I do like what you have there."

"Thanks, I knew you would. You are totally a dirty old man."

"Completely guilty. That I am."

"So, Steph tells me that she wants you to kind of be part of our group, to be one of our friends."

"Yes that's what we talked about."

"You know that we have this special bond between us, that we play with each other and make each other feel good."

"Yes, she's told me all about that."

"That means that you have to make me feel good, and I get to make you feel good as well."

"I can certainly try. Hey, Teri is coming down the hall." And Kelly quickly did up one of her buttons.

Teri popped her head in the door, "Gene, I'm done for the day, and it looks like you're the last one here. Do you want me to lock up?"

"Sure, that would be great. We're almost done here as well."

As Teri went down the hall, Kelly asked "So we're alone here now, everyone is gone? Goody"

She then leaned back in her chair, spread her legs apart a bit, and stated undoing her buttons.

"I'd really like to show you what's under all of this. Do you want to see?"

"Oh, yes. Let me close my door just in case."

I got up, shut the door and turned the lock.

I went back and sat on the edge of my desk, looking at Kelly, who by know had all of the buttons on her blouse undone and pulled the sides apart to show me her nice cleavage covered in her lacy blue bra. It was thin enough that I could see the points of her nipples.

"I wore this just for you. It's the sexiest one I own. I know it's not VS, but it's what I can afford, and I really like it, especially when my titties are excited. Do like them? Come and help me take it off. It clips in front."

I went over to her and put my hands on her bra cups, and gently massaged her tits. They felt wonderful. I unfastened the clip on the front, and she pulled them apart."

"Suck them please."

I knelt down, leaned over and took first her left one, then her right in my mouth, licking, sucking, pinching. She held my head, and gently pulled me closer as I continued to alternate from left to right and back again. She smelled so nice, and sweet, and fresh, truly, amazing.

She let go of my head and shifted in her seat a bit, so I pushed away from her a bit. She was trying to pull up her skirt. She lifted up and her skirt came up past her hips. She had on a matching little blue thong, and she pulled it aside, and started rubbing her clit. She was looking right at me.

"We do this quite a bit. Where we watch each other masturbate and see who can get off first. If you're going to be our friend, then you have to do it too."

"Oh, I don't know if..."

"Come on now, stud, it's only fair."

So I sat back on the desk, undid my pants, fished out my almost fully erect penis, and started stroking it.

"Oh, you have a very nice dick. I may have to try it on for size."

We continued like this for 3 or 4 minutes, and I could see Kelly was getting more and more into it, and getting closer.

"Come here, grandpa, you finish me, then I'll do you, OK?"

I reached down and put my finger on her clit and did the circular motion thing like Tammy showed me. Kelly started rocking her hips and said "Fingers inside please", so I put in two from my left hand and slowly pushed all of the way in to her very wet pussy. I curled my fingers up and touched her g-spot, and massaged it for just a few seconds when she shut her eyes tight, tensed up, and let out a quiet, long moan, then relaxed. I looked down and saw that there was a distinct wet spot on the chair

"You're very good you know. Come here, my turn."

I stood beside her and she wrapped her hand around my cock and started stroking. Before long, she clamped her mouth around the top, and she was good at it. I had no idea how much experience she had. I mean, she said she had fucked three boyfriends, but was there much oral in there, no way to know. But she stroked, she cuddled, she loved, she really wanted to please me, so it didn't take long for the feeling to start deep inside, and I said, "It's coming pretty soon"

"Good," and she put the head back in her mouth, and twirled her tongue around and massaged the underside of the head. Just as I was about to let go, she took it out of her mouth, held the end just above her boobs, and continued to stroke, and I ejaculated on her pert pink breasts. She continued to stroke me slowly, rubbing the head around in the cum that was on her breasts.

"So that is how we help each other out. Welcome to the club." She put the end of my cock in her mouth and cleaned it off, releasing me she said, "There you go, good as new. I need something to clean myself up. I can't get dressed back up like this", swiping a finger across the goo on her tit, and then licking her finger. "I guess I should have swallowed, and saved the cleanup, oh well -- next time."

I handed her the box of tissues from my credenza and she wiped up, tossing them in the trash. She straightened up her panties, pulled her skirt down and re-clasped her bra. As she was buttoning up her blouse, I asked, "Does Steph know you're here with me?"

"Not exactly, but I will tell her. She might be just a little pissed, but then I didn't fuck you, and we only did what I and the others do ourselves anyway. I think, though, if we are going to fuck, we probably should tell her, don't you think?"

"Yeah, that's a good idea. She's getting a little attached to me it looks like."

"Yes, I know. It shows. So you only have the two virgins left. I really think that you'll have to play with them too. I'll bet we could set something up where you could get them both at the same time,, that would pretty cool, no?"

"Only if Steph is OK with it, I don't want to get her upset."

"Don't worry, we'll figure something out."

She finally finished getting herself all arranged "Everything look OK?" she asked.

"Perfect", I replied. She leaned forward and planted a big kiss on my lips, along with a lot of tongue. "Thanks, that really was fun. We'll definitely have to do it again. All done? Then let's go, I need to get home soon."

And we walked out of my office, down the hall, into the elevator and out.