Dating Ellen -- My Best Friend's Mom

I confessed that I was 'having feelings' about her. I was seriously understating what was going on in my head. I expected to eventually be rebuffed by Ellen since she was about sixteen years older than me. I was pleased that she let me sustain the fantasy of us being together.

After my confession, we stood at the edge of the surf, Ellen came into my arms and gave me some long and deep kisses in between telling me that she felt the same way. We changed over from holding hands to walking with our arms around each other so that we could be closer. I was sinking fast.

After we'd started to walk I had to address the pressure issue between us before going much further; I asked, "Does our age difference concern you?" I felt sure that it would and my fantasies would implode.

Ellen stopped and kissed me again. She said, "No, but let me explain because I know this will come up again and again in your thinking unless we put it away. I've watched my son and you develop since you were twelve. Age does not correlate with maturity, and you are a lot more mature on that basis than Jake. You're my equal now, at least intellectually. You have life goals and timelines and think ahead, whereas all he thinks about are where his next beer or party is going to come from. You've moved on into adulthood, and he's still living out his teenage years.

"I share almost all the same values that you do, plus I'm a little immature and inexperienced -- witness me having a child when I in my mid-teens and then hiding away since then. That wasn't a terribly smart thing to do although I love him with all my heart.

"My social life happens to revolve around my job at the club. I don't date. I've kept it that way, at least until now. You've seen me at the club, but socially I've kept people, especially men, at a distance. There's nothing at the club for me except lots of friends. You fit in so well with everybody there, too. I know we could have the same friends and lifestyle. Moreover, I'm ready to make a commitment again, at least with you. Age does not enter into the equation."

I kissed her forehead, "So, you're willing to be my girlfriend?"

Ellen hugged me, "Absolutely. Oh, yes, please." She pulled away and looked at me to see whether I was sincere.

I think we both wanted to commit for life, but we both held back in the interest of realism. I had about a million more questions, but I needed to get my act together better to ask them. We went to dinner at a place called the Crab Shack. Ellen had never eaten there and loved the place because it was so informal, yet had a great menu, many entrees with freshly caught fish. We had grouper sandwiches.

I asked Ellen some pointed questions starting with, "Why would you date somebody about sixteen years younger than you are?"

Ellen took my hand in hers and said, "Because I like them -- a lot -- and want to spend time with them. Why do you date at all?"

I nodded and said, "Same reason. What are you doing next weekend?"

She laughed, "Going on a long date with you, I hope. Saturday at noon again, please. I have all weekend from then on. There's nothing special going on at the club."

We talked about what she'd like to do, and planned a couple of excursions. One of them involved looking for a place for me to live now that I was a sure thing to graduate and would have a good-paying job.

I took Ellen home after the Crab Shack asked us to leave because they wanted to close. We'd sat and talked for hours even though we finished dinner. We made out as we parked in her driveway, but I kept things prim and proper. I had a longer-term view of this relationship and didn't want to fuck it up by trying something stupid like making some kind of move on her body.

I was back in classes the next morning, and even more motivated to do well than I had been before adding a 'girlfriend' to my life. That said, my head was filled with thoughts of Ellen, and every single one of them was romantic.

I sent some photos and crazy emojis to Ellen every day during the week, mostly to let her know that she was always in my thoughts. She always responded with the same. I realized that I didn't have any pictures of her, and resolved to fix that over the weekend. Upon request, she did send me at least one nice formal shot of her sitting in her office at the club.

I was at Ellen's door at noon on Saturday, as planned. Her welcome reminded me that she was my girlfriend and that nothing had changed in the days we'd been apart. I got kissed and hugged like she hadn't seen her lover for a year. I liked that.

We had lunch at the Cantina, catching up on what our weeks had been like, and then we walked the beach. Our starting topic was about open, honest communications in a relationship. We agreed that if it wasn't happening naturally, then some kind of routine process needed to be set up to foster opening up to each other. I suggested a weekly time to share feelings and emotions seemed like a good starter idea.

We then had a silence as we walked through the sand, before Ellen asked, "How much sex have you had? Are you quite experienced?"

I shrugged. "I've been with six girls, all in college. Two of them were sort of fuck buddies. We had sex when we went out, but we didn't go out all that often unless we were horny. The last time I had sex was about six months ago. Other than that, I rely on my right hand and the Internet." I blushed at my admission, but I'd given it in the interest of honesty.

"So, you admit that you watch porn?" she teased.

I laughed. "Ellen, you'd have a hard time finding someone my age that doesn't watch porn -- male or female."

I turned the question back on her, "What about you?"

"Oh... errr... well, I had Jake when I was sixteen. Big mistake, kind of. I was married for four years, but Tommy was sleeping around and I wasn't. I tried to be a good wife, but Tom was having none of it. Since our divorce I've been with three other men. I thought each of them had potential but rapidly discovered there was no real chemistry in any of those relationships. Two of them lasted over two years, and the last attempt I made ended five years ago."

"I'm sorry that didn't work out for you. Did you lower the bar?"

"No, if anything I raised it. I've seen some of the men at the club misbehaving, plus more than a few have politely propositioned me in some way. I get hit on almost every week. I guess they figure that a single, divorced woman would be an easy mark. I just shrug and figure that it's part of the job."

I chuckled, "You didn't put enough of a description out there. How about a beautiful, hot, single, divorced woman with a sparkling personality, fabulous fashion sense, empathy, emotional maturity, a great mother, and an even greater girlfriend. Of course, you're going to get hit on. Are you ever tempted?"

That earned me a passionate kiss. "You say the nicest things, and no, I am never tempted. For one, every man that comes on to me is a bore and almost all are married. I don't want a one-night stand or a quickie behind the pro shop at night, and certainly not with a married man. I want a stable long-term relationship with somebody that I like and that I love. I also expect a relationship to last for years. You should know that I'm a one-man woman." She looked at me to see my reaction.

We reached the jetty, and turned around to walk back the mile-plus that we'd come from my car.

"I'm in full agreement with you."

Ellen stated, "For almost all of our kissing and making out, I've been the initiator. I've set the scene and led you into it. Here are some key questions I want you to answer. Why haven't you initiated with me? Why haven't you tried to feel me up -- to paw at my breasts or more? I've all but pushed a naked breast into your body."

I jerked around to look at her. "Ellen, I highly respect you. I feel something great building between us and... well, I just don't want to screw it up by being a dumb college kid that thinks the world and women owe him privileges. I'm not skilled in dealing with a lot of women, as I told you. I don't know your signals that would want me to initiate or to take liberties with you in some way. Worse, I'm not sure I'd know your 'getting worried about what's happening' or your 'stop' signals."

"Thank you. I hadn't considered most of those things. I thought you were still hung up on the age thing."

"I saw it as an issue, but after we talked about it last week, it's no longer at the forefront of my mind. I just think of it as another factor in our adventure in life together. You've made me feel older than I am."

Ellen hugged me to her as we walked, "Then, here's the way I would like for us to be from this point on. First, either of us can initiate making out. If you haven't figured it out, I really like doing stuff with you -- kissing and I hope more. Second, I am assuring you that you have permission to cross what you think are my boundaries regarding feeling my body -- any part. I will tell you forthrightly if we discover some boundary that I don't know about. Third, I assume you'll be discreet and not talk about what we do."

I teased, "Except with you, I assume."

Ellen rolled her eyes. "I will enjoy talking about it with you. Doing that will turn me on. I want you to turn me on. This conversation is already making me wet, and that has nothing to do with the water splashing around our feet."

I gently pulled Ellen to me and we stood still and I wrapped her in a hug and pulled her tightly against my body, pushing my groin against her. I swelled and guessed that she'd be able to feel me. After we kissed, I said, "Just so you know, I like those rules and that they apply in both directions."

We had an early dinner at the Classic Grill. We raced through the meal because it was standing in the way of our Saturday night and whatever would happen now that some barriers to our interaction with each other had been removed.

I drove us back to Ellen's house about eight o'clock. We sat on her sofa, turned on the TV to nothing memorable, and started to make out. I initiated the session to her delight. I got an approving smile and then some very passionate kisses.

I knew about erogenous zones and focused on those with my kissing, licking, touches, and so on, until I thought Ellen was panting slightly. I took that as a sign, so I slid one hand up over her breasts on the outside of her blouse. To my surprise, she appeared to be without a bra, and I was sure she'd been wearing one that afternoon. I felt it through her blouse several times what I stroked up her back. She'd dispensed with the apparel since we got to her house.

Ellen pushed her chest into my palm, and whispered, "Yes, please. Get more physical."

I moved my hand around and felt her nipple harden beneath the material of the blouse. I did the same to the other breast. I then leaned over and sucked on a nipple through the material. Ellen moaned and pushed into my mouth. I spent a few minutes at this new hobby, leaving two saliva-soaked areas on the front of her top, and two hyper erect nipples pushing through those areas.

I asked, "Am I allowed to unbutton things?"

Ellen looked surprised at the question and answered quickly, "Yes, yes, yes, please. You don't have to ask. I want you to feel skin from now on."

I took my time and unbuttoned the six buttons along the front of her blouse. Ellen was panting and pushing into my hand. I even pushed her hand away when she went to help me. She smiled and we went back to kissing or even just allowing our tongues to touch in the hot air between us.

I peeled the blouse away from her upper body, and gently stroked the back of my hand across the entire real estate, enjoying the sensation of her aroused nipples on my hand. I returned to sucking on her teats only with no intermediate barrier. Ellen moaned and held my head to her chest. Occasionally, she'd moan in pleasure.

We crossed another hurdle when I felt her hands pushing off the shirt that I'd worn. I didn't want for her to worry about it being a pull-over. I tossed the shirt aside in two seconds and we brought our chests together as we hurled together in a hot kiss. She felt fabulous, and I had become very aroused.

Ellen also didn't wait to go further. She rubbed the front of my slacks, zeroing in on the hardness there trying to get out and do some mischief. I pushed up into her hand to show my own approval at what she was doing.

Ellen had on Bermuda shorts. I duplicated her move in her private area on the outside of her shorts. I could feel the heat emanating from that part of her body almost like she had an electric heater hidden inside. Again, she pushed into my hand so that I made firmer contact with her sex, albeit over her shorts.

I rubbed and kissed, often revisiting her breasts. She rubbed, and then pulled down my zipper and wormed her hand inside my pants. Oh, fuck, this was heading in an amazing direction. I redoubled my efforts at pleasing Ellen, but she seemed to be ahead of me.

My shorts parted around my groin and Ellen had my raw cock in her hand... and then in her mouth. My God, I was getting a blowjob from the prettiest woman on the planet. I could no longer reach below her waist in our position, so as she bent over me, I stroked her back, her hair, and her breasts. She seemed to be purring around my shaft. I was panting very hard. Where had all the air gone.

I let Ellen work on me for only five minutes, but then I felt as though I might explode. I didn't want that. It was too soon in our evening together. I pulled her up and nudged her back on the sofa. I watched her eyes as I unbelted, unbuttoned, and unzipped her shorts, and then pulled them down her legs. She raised her hips so I could do that. I removed her lacy underwear next, leaving her deliciously nude. She grinned at me and spread her legs wide.

We almost never broke eye contact. The emotions there were intense, yet there was not a doubt on either of our parts about the arc of the evening. We both wanted what was happening.

I stood and shed the rest of my clothes, but then I moved between her legs and used my tongue to make a long swipe from her taint up over her mons. I made sure to bury the tip as deep as I could in her very moist slit. I then came back and started to use my mouth to toy with her labia, sucking in the lips i, and then licking all around when I wasn't thrusting with my tongue into her.

I added fingers to the game, penetrating her and searching for a spot inside her where I'd learned she'd find pleasure. When Ellen jerked and moaned simultaneously, I focused my fingers there as my tongue zeroed in on her clitoris.

Perhaps it was the aromas or the tastes, but my whole being had become focused on bringing Ellen pleasure. She was a piece of fine porcelain china, I wanted her pleasure more than anything. Ellen started to hump my fingers and mouth. I was sure that what I was doing was working for her.

Ellen started talking; swearing actually. "Nobody... has even... oh, fuck... had me so worked up... or so in need of... fucking. I hope you... don't plan to ever go home... you will have to... do this until... the end of time.""

I promised her my undying devotion even into future lifetimes and generations. Ellen orgasmed right in front of me. I was amazed at what I'd done. I'd never had a girl do that before with me. Oh, I'd seen the fake shots in porn movies, but this was something else and there was no doubt that it was real.

Ellen's body almost levitated off of the sofa as she pushed her mid-section up into my hand and my face -- my tongue, really. She had been panting, but that all stopped as all motion of air in and out of her body ceased. What air she had left exhaled by way of a loud and long moan. "Oooooooooh, Joooooossssshhhhh." My name had never sounded so sexy or so good, hearing it from somebody else, somebody that I loved.

I held Ellen and we kissed more and more, with lots of tongue. Our naked bodies writhed together so we could both feel each other's nakedness. She said, "I like the way we taste -- that you taste. Now, we need to complete our union."

Ellen lay back, pushed her pussy to the edge of the cushion and spread her legs wide. She even reached down and spread her labia so that the interior pink of her pussy showed, and even the opening to her vagina.

Ellen said, "Make love to me. Put yourself inside me,"

I did, and it was love, too. My mind, body, and spirit were hers. I'd obey any command she gave me, providing it involved making her happy and giving her pleasure. I moved forward, tentative to be sure of her consent and desire, and then slid my hardness into her soft and warm interior.

I leaned forward and we kissed the most epic kiss of any we'd shared. "I love you," I stated.

"And I love you," Ellen said. "This is... YOU are the best thing that has ever happened to me. Oh, never stop." She had tears of joy in her eyes, and then I realized that I did, too.

We lasted about fifteen minutes, and that only because I withdrew completely for over a minute about midway through rather than end so quickly. I filled up Ellen's little cunny with my sperm. She was joyful about what we'd accomplished.

We kissed some more and then I apologized. "I should have used a condom... and what about birth control... and when I pull away, we'll drip on your sofa and the carpet... and..."

Ellen kissed me to stop me talking. "Stop worrying. I don't like condoms. You never need to use one with me. I'm safe, and I'm on birth control, and lastly, forget about our drips of passion. I want many, many more. Heck, I want them all over the house and especially in my bed."

We made out for a long time. I texted my parents that I was staying over a 'Jake's house'. I wasn't quite ready to announce Ellen to them, just yet. They didn't know that Jake had his own apartment.

We made love twice more that night before going to sleep with Ellen cuddled in my arms atop my body and purring. We'd made a lot more drips. Things kept getting better and better. We also liked our nudity with each other.

* * * * *

We were almost inseparable over the next month, except for my school and her job. I studied at her house just to be near her. We had meals there or went out together. We spent a lot of the time in her bed making love. I wondered whether life could get any better.

"What do we tell Jake?" I asked one evening.

With my best male friend living in town in his own apartment with three other guys, I knew it wouldn't take long for him to get wind that something was happening between his mother and me.

Ellen laughed, "I don't care what he thinks. I only care what you think."

I pecked at her lips and said, "I think I want to never stop loving you."

"Good. I feel the same way. Just to acknowledge it, this is New Relationship Energy or NRE. We're in the honeymoon phase of our relationship. Our feelings for each other are intense and euphoric, and very physical -- which I love. Over time, the intensity of our feelings will diminish and become more stable and balanced. We'll also start to see faults in each other that we'd like to change or eliminate."

"Do we wait for the next phases before saying anything to anybody? I want to be with you every second."

Ellen thought and said, "Eight more weeks -- and that's an arbitrary time period. We wait eight weeks before saying anything to anybody else, other than we have 'someone special' in our lives. What do you think?"

"I agree. I think we can hold them off until then. My parents think I'm over here spending time studying and playing video games with Jake. Jake thinks that I'm wrapped up with my final courses."

The next eight weeks flew by as spring arrived and headed towards summer. Ellen and I saw each other every weekend and most weekday evenings. On the party weekends, I showed up to help her at the club and we ended up going to whatever function the dance or occasion turned out to be.