Best Friend Stacy

I was lucky enough to have a most incredible experience, and it was all because of my best friend Stacy. Remember the TV show Will and Grace? Well, that was us, just the opposite. I am the straight guy and Stacy was my gay roommate. Stacy and I met in college, became friends after freshman year when we lived in the same dorm, and throughout school, just remained best friends.

We would hang out together all the time, console each other through dates gone bad, and help study together. We just had a connection and perhaps because there was no sexual tension between us, we just clicked in a different way. Sure we scoped out women together, but we had different tastes and agreed not to compete for a mate.

Now Stacy was no slouch. She was all of 5'10", lean and long, wavy brown hair. She had pretty brown eyes that sparkled when she talked about her favorite subjects, like music, art, cooking. And she was very fit. Always went to the gym and sometimes we would go to the gym together. I think some people in college thought we were a couple, but I knew from day one that she was not into guys, and she was a bit scared to tell people, so her status was not that openly gay. And she trusted me with everything and I came to trust her as well.

We both did great in school and ended up landing jobs in Boston after. We decided to live together to help with expenses, and found a great two-bedroom apartment in the North End. Of course we were single upon leaving college and decided to help each other out finding a significant other. We hung out in some cool restaurants, shops, gym and bookstores, and had an occasional date here and there. But our dinner conversation frequently dealt with our perpetual single status and little luck with women.

I think the fact that Stacy was a bit insecure with her sexuality made it a bit difficult for her to find someone. And I was so busy trying to climb the corporate ladder, that finding time to cultivate a relationship was my limiting factor.

"What are we going to do Jason? We're going to be a couple old maids together, aren't we?" Stacy mused, one evening hanging around watching tv after dinner and long days at work.

"Don't worry Stace...we'll find someone." I continually tried to reassure her as well as myself, but the nights and lack of sex were just getting old.

"Maybe we're hanging out in the wrong places?" Stacy said.

"I don't know...all the magazines say to go to places where there is someone with common interests. Like classes, bookstores and gyms. But it's so cliché...no one wants to be picked up at the grocery store or gym. Everyone is so busy and wants to get on with their lives." I tried to sound convincing for both of us.

"Well, I have to start a class for work, and maybe I'll find someone there..." "Yeah, maybe you will Stace...I don't know why you aren't hooking up. You're quite the catch. I told you this before, that I'd do you if you were into guys. Guys are always checking you out."

"You're sweet Jace...guys just aren't my thing. That's probably why we get along so well together, because there isn't that sex thing between us."

"I agree. That would ruin our friendship."

"But this BOB thing is getting old." Stacy said. She knew I knew that this was her battery operated boyfriend. We had this joke for years.

"Need some new batteries perhaps? Let me help you out there. Get it for me and I'll change the batteries."

"Very funny guy. I can quite do that myself, thank you," Stacy said, giving me one of those looks.

"You know Stace, it's just hard for guys to compete with complicated female sexuality. You have access to the equipment 24/7, and guys have to figure that shit out."

"Perhaps. Guys are simple, right? Just a quick screw and you are happy, is that it?"

"I'd take that now, that's for sure. But we're not all pigs, you know."

"I wouldn't know. I just always knew I love women. That's my destiny, I guess."

"I love women too. And I love you Stace. I'm going to bed. See you tomorrow."

"Good night Jace. And I love you. You're my best friend."

And so it went for a few months in our new lives in the big city. One weekend, some friends from work were going out and about 10 of us went out to a jazz club. One of the women in our group named Chris brought a friend, Megan. Now Megan was quite the looker. Blonde, curvy and dressed to show off all her assets. Short skirt, boots, sleeveless blouse with some exposed cleavage.

I tried with some success to sit near her. Chris and I work together, and so it seemed natural that we hang out. And luckily since Megan knew just a couple people in the group, that she sit near us too. And even more lucky, Megan and I seemed to hit it off. We talked, laughed, listened to the music and had some drinks. She had this habit of reaching out and touching my arm when she made a comment, or leaned in close to talk over the music. It was very sexy. And she smelled so good. I was definitely attracted to her and wanted to ask her out.

Which I did after the party broke up and she said yes!

I told Stacy of course, and she was very happy for me. She asked me all about her and I couldn't stop talking about how she looks and how we talked effortlessly about things and how she agreed to go out with me the next night. Stacy said she'd love to meet her and I told her I might bring her by after dinner the next night.

We made plans to go to dinner the next night, and what a night we had. An Italian dinner that I knew nearby was outstanding. Great food, abundant Chianti and then a stroll afterwards, arm in arm. Again, Megan looked fabulous. Again with a skirt and blouse, heels and cascading hair down her shoulders that she played with when she talked.

I told her about Stacy and that she was my roommate, and that she was gay. I wanted Megan to know that she wasn't my girlfriend, but best friend for years. So we wound our way back to our apartment and Stacy wasn't home.

"Would you care to stay for a drink then? I'm sorry Stacy isn't around. Perhaps she'll be home later. I'd love for you to meet her."

"Sure Jason. That'll be great. What do you have?"

"We have a pretty well stocked bar. Do you want a drink drink, or wine perhaps?"

"How about a night cap drink. Do you have brandy?"

"Sure do. I traveled to France in college, and spent time in the area that specializes in brandy, so we do have a couple good choices. Let me pick one out for us."

"Sounds good. Tell me about your time in France."

I picked out a nice Corvoisier brandy and we sat on the sofa and chatted more, sipping our drinks and shared our histories and family stories. She was just so nice and easy to talk to and pretty to look at. I couldn't believe my good fortune having this beautiful woman in my apartment.

"Excuse me for a moment Jason. I need to use the ladies room."

"Down the hall and to the left." I stood, and pointed the way.

While she was gone, I dimmed the lights a bit, put on some classical music and hoped she was thinking what I was thinking.

"Hmmmm, what have we here? Are you trying to seduce me Jason?" Megan asked softly, returning to the living room. I wasn't sure, but it seemed as if there was a button more open in her blouse.

"That's a distinct possibility my dear Megan. You are a beautiful woman and I would love to kiss you." Megan walked slowly towards me and we looked at each other, both emboldened by the evening and a bit of the brandy, and I smelled the intoxicating aroma of her perfume, and the brandy on her breath.

"Well, what's stopping you then?" She whispered rather rhetorically, and closed her eyes just before we kissed. It was tentative at first, our hands around each other's shoulders, and then after a couple moments of the most incredible first kiss I've ever had, we leaned apart, looked into each other's eyes, and smiled.

"That was a great kiss," Megan said, again allowing me to inhale her scent and caress her hair.

"Shall we sit?" I edged us towards the sofa again, and we sat down, this time much closer than just before.

I put my arm around her and drew her nearer so we could kiss again. Her lips and her touch were electric. I know it had been a while, but she was so incredibly feminine and the combination of the dinner, the drinks and her smell got to me. We kissed again, a bit more firmly and I felt her tongue at my lips. Her hands drew my face to her and we spent the next 10 minutes kissing like teenagers. I broke apart to breathe and to kiss her ears and her most wonderful and sensuous neck.

"Oh god...Jason...that feels so good. It's been a long while since I've been with a man like you. So kind and smart and funny"

I just murmured my agreement and kissed and bit her neck, trying to find the most sensual place on her body. We were both breathing quite hard and I wanted to find more and more erotic zones on this wonderful creature. I kissed my way back up to her mouth and we hungrily devoured each others' mouths in lust-filled kisses.

Then we heard the door open, and Stacy walked in. I'm sure we looked a bit of a mess, and the atmosphere in the room was quite apparent.

"Hey Stacy...I wanted you to meet Megan." I said, in a rush.

"Hi Megan, nice to meet you." They shook hands and I tried to make like nothing happened, though I don't know that I needed to explain anything.

"Sorry to have interrupted you guys...I'll just head off to my room," Stacy said, with a knowing look and a wink to me as she sashayed down the hall.

"Well, that was a rather awkward first greeting," Megan said, obviously a bit embarrassed by this introduction.

"Oh, don't worry. We'll get to talk with her later. Where were we then?" I asked, reaching out to stroke her hair and leaned in for another kiss.

"Wait Jason. What if she walks in again?"

"She won't. We'll be fine." I kissed her neck and nibbled at her ear. I felt the mood returning and hoped that Stacy's entrance wasn't a total deal breaker.

"That's were we were I think. Keep doing that Jason. That feels so fine. Mmmmm..." Megan moaned in my ear.

I caressed her arm while biting softly at her neck and down to her collar bone. I felt goose bumps on her arm and reached to feel her breast, hoping not to get stopped. Instead she pushed into my hand and moaned again as I felt her soft, full breast. Her hand came to mine but not to pull me away but to draw me in and pulled me harder to her chest.

I kissed her soft lips again and she ran her hands over my chest and arms and hair. Now it was my turn to moan as she touched my body.

"Jason..." she whispered, short of breath."

"Yes."

"I have to tell you something."

"What?" I said, kissing her neck some more. God, she had an incredible neck.

"It's that time of the month for me...we can't...um..."

"It's ok...there's other things we can do, right?" I looked at her smiling and caressed her breasts, feeling her nipple through her scanty bra.

"That's true. Most guys are kind of grossed out and done with that issue."

"That's too bad...but I happened to be turned on and I know there are some things that we could find that would be almost as fun."

"I think so too...I get so horny sometimes with the hormones. And this is one of those times."

"I think that's good...very good." I reached forward to unbutton her blouse and she sat back and smiled and looked at me with a lusty grin. "God, you're so beautiful Megan. I can't believe you're single. Any guy would kill to be with you."

"You're so kind...I guess you're the lucky guy tonight. And I think I'm the lucky girl."

I exposed her chest and she helped me the next step releasing the front clasp of her bra..

"Now that's convenient. Saves me fumbling in the back." I sat mesmerized as the flesh of her firm tits came into view and I reached to hold the weight of them in my hands and stroked the soft skin on the sides and undersurface. Megan sat back and looked down at my hands on her and then back to me, her eyes now half open.

I felt her nipples harden further under my hands at their exposure to the air and to my touch. I stroked them softly and marveled at her beauty. I leaned forward and kissed the top of one breast and kept my hand on the other, squeezing, pulling and caressing her nipple. I kissed my way down to her nipple on the other side and heard her moan louder in my ear as I took it into my mouth and sucked, softly at first and then harder, struggling not to bite as I wanted. Her hand wrapped behind my head and her fingers kneaded my neck and pulled me to her wanting body.

I let my other hand go further south and felt her legs and pulled up her skirt, exposing her bare thigh above her stocking. Her legs parted and I felt the heat emanating from her core. I stroked her bare inner thighs, still sucking on her nipple, trying to find the right pressure and location that would elicit the most response from her. She was very telling in her moans and words in my ear, telling me, 'oh yes...right there...just like that...keep doing that...oh god...' That was pure music to my ears as I continued to tease her and held off going right for the goods.

I stopped for a moment to let her catch her breath, and continued to stroke her thighs.

"Why are you stopping Jason? Please...don't stop"

"Oh, I'm not stopping. I'm just taking in all this. You are so incredible, how you smell, how you feel and how lucky I am."

"Please continue to show me then..." She hungrily pulled my face and mouth to her neck and breasts as my hand brushed up against her panties. That elicited another strong moan and she slid down on the sofa to give me better access.

I let my thumb caress her outer lips and felt her wetness, still sucking on her tits. I slid her panties aside to stroke her pussy and she was so incredibly wet. She was breathing shallow, short breaths as my fingers probed and caressed her center.

"Oh god...there...more...right there...yes!" She said, as my finger found her clit which was protruding proudly and aching for attention. I knew she didn't probably want any penetration going on, but she was so aroused by what I was doing that I thought she would come any minute.

I continued to rub her clit and suck on her nipple as she was grabbing my head with one hand and squeezing my arm with the other that was behind my back.

I continued to do what I was doing and she held my head to her tits and her other hand held tight to my wrist, as if I was going to stop doing what I was doing. I held her lips open with a couple fingers and with the other softly stroked her clit slowly and gently and then alternatively circling around, trying to find exactly what and where she liked it. And sure enough, I found the right move.

"Oh yes...there...like that...there...yes...yes..." she moaned and I knew she was close. I didn't stop doing anything that I was doing and then in a few more moments of this same thing which she clearly liked, she came with a cry. I could barely breathe, being smothered by her incredible tits and her legs squeezed together trapping my hand to her spasming pussy. I held her there as she came and kissed my way up her neck to her face and mouth, holding her tightly as she climaxed and then calmed, feeling her breathing return to normal.

"Oh god Jason...that was so needed you don't know, especially when I'm having my period. But I was just so horny and you just made me feel so special..." She was tearing a bit from the emotion, I guess having a good orgasm plus the hormones of her cycle.

I held her close and told her how beautiful she was and how turned on she made me and how I loved making her come like that. After a few minutes, she relaxed her grasp and said, "Now perhaps there is something I can do for you?" She looked at me with that lusty look again and ran her hand over my chest and arms.

"Now what might that be dear lady?" I asked, still stroking her hair and taking in the sight of her state of partial dress and hoping she was thinking what I was thinking.

"Seems I can think of something to repay the favor," she said, reaching for my thighs and stroked my legs. "You've been a very good boy and good boys get rewards."

"I like rewards."

"I think you'll like this one." She reached for my groin and at the touch of her hand to my hard cock, it was my turn to moan into her ear. "What do we have here? Is this the kind of reward you had in mind," she asked, rather rhetorically, stroking my hardness, feeling my length, gauging my erection. The first touch of her hand on me was just electric and I could hardly speak.

"Definitely...oh Megan...it's been a long time for me too."

"Just relax dear Jason. I think I know what might make you feel better." With one deft hand, she started to unbuckle my belt and then pulled the other hand from behind my back and sat sideways to me so she could open my pants and then she reached one hand inside my pants and felt my cock through my briefs.

I gasped again at the feel of her hands one layer closer to the skin of my aching cock. She caressed there more until I was almost going to come right then.

"Anxious, aren't we?" she said softly, seeing a spot of wetness emerge through the cloth of my underwear. "Would it be better if we got these off?" She reached her hand under the waistband of my shorts and I raised my hips off the sofa so she could pull them off some. She still hadn't touched my cock directly and I was so close to coming it wasn't funny. "Now that's better". She stroked my inner thighs and held my balls with one hand, feeling them tight with need. "What a beautiful cock dear Jason...so hard...so ready..." She kept talking softly to me, staring at my cock and I too was staring at her hands nearing my cock.

"Please...Megan...please..." I began to beg.

"Please what Jason? Tell me..."

"Touch me...please"

"You mean here?" she said as she stroked my thighs and balls.

"Yes...and..."

"Or here?" she said, as she drew her fingertips starting at the base of my cock, pointing straight up to the ceiling. "Or here?" she said, painfully slowly inching towards the tip of my cock. "Or like this?" she said, finally encircling my cock with her hand, softly yet firmly making strokes up and down.

"Oh yes...like that...that's good. It's not going to take long Megan..."

"It might take a little while. I'm rather enjoying this." She started stroking firmly up and down my cock with one hand at a time, and then both hands at the same time, as if to size my length by how much of the tip stuck out as both hands grasped side by side.

"I can't take it much longer...that feels so good...your hands are so soft, so good...god...please"

"Begging now are we? I like when I can make a man beg with just my hands."

First, both hands went up and down, alternating. Then each hand one at a time going up, and then both hands on the down stroke. I was panting and starting to sweat. This woman knew how to give a hand job. Then she stopped stroking up and down and used only the tip of her thumb at the sensitive tip and just stroked there. That was so crazy I could hardly stand it.

"Oh god...that's amazing." I gasped.

"Feels good there? Like this?" She was really studying what I liked best. She kept stroking the groove on the undersurface of my cock until I was positively squirming and leaking. She kept taking the drops that came out and rubbed them into the skin at the tip of my cock, creating the most pleasurable friction imaginable. Her other hand was stroking my balls, gauging my arousal and encouraging my impending climax.

She resumed stroking at a deliberate rhythm, not a fast jerk off, but a knowing build towards an inevitable end. Her strokes were firm and steady, and she looked up at me and I at her, as she knew my orgasm was close.

"It's close, isn't it? I can tell...you can come now Jason...come for me...I want to see you come," she said breathlessly, watching my face intently and I struggled to keep my eyes open staring at her hand slowly and firmly stroking my cock, getting ready to explode. That combined with her words edging me on set me over the edge. I came hard, shooting my cum up to my shoulder and chest, and then the next spurts landing with an audible sound onto my stomach and then lower down and my orgasm subsided, coating her hand with my hot fluid.