A highly respected and well trained female therapist helps her young male client with his problems with women in a way only she can…
The first thing I was taught, and mentored on countless times since, is to not have any romantic attractions to my patients. But as an older woman, how can I not feel drawn to such a handsome young man when his very problem is being single? In my 20’s I studied to become a therapist and since then I’ve helped many people overcome their problems. Now I’m in my late 30’s and am more than capable at my job. I’m not married currently, my husband left me for my secretary of all people if you can believe it, but I still have my son in grade school. Perhaps it’s my motherly instinct, or my desire for a man, that has me so invested in this young man’s problems. His name is James, and he’s just barely 20 years old, but he came to me saying no matter what he’s tried to do, he seems unable to find a woman that’s attracted to him. He feels completely ignored by most people, most of all women, and that he just wants to find one to be happy with. I sit and listen to his problems in our sessions, and I try to keep a neutral expression, but secretly I want to walk over to the couch and ride his cock till it explodes inside me. If I did I’d surely lose my license and any respect in my field. “Don’t fuck the patients!” is what my male mentor always told me.
I have another session with him this afternoon, and I hope he’ll come to me with better news, because last night I went on a first date for the first time since my divorce and it was terrible. To start, we met online, and in my profile I only have face shots of me. Usually I hear that’s something overweight women to to catfish, but I do it because my body attracts the kind of guys that only want to fuck me, and it’s easier to avoid them if they don’t know what my body looks like. So I went to dinner with this guy and as soon as he sees me, I can tell his entire game plan for the night turned to trying to fuck me. He didn’t come off as interesting to me, nor I to him most likely, and we called it off early. Honestly though I might have let him get lucky simply because it’s been so long since I have, but I want to feel like there’s more than just your need to rail me in order for you to do so.
So I sat in my home office, the area of my apartment I keep most of my books to make my patients feel like it’s more professional than just my living room. My secretary, the new one obviously, knocked on the door and said James is here to see me. I thanked her and had him sent in. I also said she’s free to leave since she has to pick her kid up from school before we’d be done. As soon as James sits down I can tell he’s not doing better as I hoped. In our last meeting he seemed happy that he finally gotten a girl’s number and I presumed they had been talking and gone on a date since last week. Instead of a smile he has a blank expression, like the happiness of life has been drained out.
“Hey there, James. I see you don’t look to happy this afternoon. You want to tell me what happened since last time, I remember you left here pretty happy.” I told him.
“I’m just feeling like it’s not fair anymore.” he responded.
“What do you mean by that?” I asked.
“So this whole time I’ve been telling you my problems, I’ve always had the thought that if I was simply more “dominant” or “masculine” as they say I”d have better luck. So I eventually manage to get a cute girl to give me her number like I told you, right? She’s not like a super model or anything, but she’s cute enough. Not like I’m gonna complain. But we talk for a few days, everything’s fine. I’m genuinely surprised at how easy this seems to be, like once it happens it’s as easy as breathing, so I suggest we meet in person. She agrees and is excited like me, and we met for a classic dinner and movie. The dinner went as perfect as I though it would, nothing I saw went wrong. But at the movie she ran into a old friend from highschool and it derailed the date as she became more focused on her friend than our date.” he explained.
“So this friend she ran into, was it another girl or a guy?” I asked him.
“A guy. Nothing special I though, but she seemed like I was her source of entertainment until he came along then she dropped me to focus on him. When the movie started she came back and apologized to me for going off like that so I thought no harm done necessarily. She came back, and said sorry, so I won’t be mad. Later that night I dropped her off and she invited me up to her apartment. I play it cool and agree, so we head upstairs. It looks like I’m finally going to get some action when she takes my pants off and then she freezes.” he continued.
“What happened then?” I asked.
“She said, and I don’t know if this was a lie to make me feel good or the truth, that my dick was “too big” for her and she thought it was going to hurt her. All these years I’ve heard over and over that women chase after men like that, only to have that very thing be the excuse for not getting any. She kissed me, and I left right after. I told her I had fun and that we can just forget about the ending the next morning, but she’s ghosted me since then. Worse still this morning I saw her posting pictures of her and that guy she ran into on a date but nothing of us two together.” he finished.
“That is pretty rough.” I responded before he started speaking again.
“I’m just confused as to what a woman actually wants, you know? I hear one thing over and over so I make myself like that, then suddenly women don’t want that. I just don’t get it.” he said. I felt so bad for him. Even as a woman everything he said makes sense. I just wants to lay his head on my boobs and rub his hair. We kept talking and that feeling only got worse for me. I could see my diploma and my license hanging side by side on the wall behind me in the mirror on the opposite wall. Then I looked back down at him and wondered if one time would really hurt? I knew damn well that there was nothing I could say to make him feel better. It doesn’t take a fancy degree or any training to know the best therapy for a man is pussy. I listened to him vent his frustrations as the room went silent to me. I spaced off thinking of just jumping on him went I was brought back to attention by the shadowy figure of my secretary walking past the frosted glass of my door on her way out. The situation couldn’t be anymore in my favor. We were at my home office, no one else here, and I was turned on by my motherly drive to help this poor boy.
I reached behind me and untie my ponytail and let down my long flowing chocolate brown hair. In the middle of him speaking, I without listening, got up and walked over to him, unbuttoning the top two buttons of my blouse as I went. I put one leg on his side and the other on the other, sitting on his lap firmly straddling his legs between my own. I brushed my hand through his hair, with my own falling around his face as I got right up to his.
“Ssh… Don’t worry about that silly little girl anymore. Let me take your mind off her, okay?” I said rubbing my boobs against his chest.
“Okay..?” he replied in a horny state of confusion, “Are you supposed to be doing this, Ms. Havelock?” he asked.
“Don’t you worry about me. We’re in my home remember, no one else has to know.” I whispered in his ear as I kissed him passionately. For a boy who has no female attention, he responded very well in kissing me back. His instincts were better than I thought, as he ran his hands up my back, then slowly back down settling around my ass which he grabbed tightly as I dry humped his lap. Fuck I was so horny right now, after he helped me remove my blouse I ripped my own bra off in heat, letting my big tits hang out in his face.
“Do these make you feel better?” I asked as I squeezed them together right in his face. My response was him sucking them like a baby. I wormed my way getting his shirt off before I stood up and unzipped my skirt, the long dress I had on, letting in fall to the floor. I kept my panties on for now, but I got on my knees in between his now spread legs and grabbed hold of the waist line of his pants. Pulling them down, I took his underwear with me. “Let’s see how big this cock really is…” I thought to myself as it sprang up out of his pants. If only I could have seen the look on my face, I probably looked like one of those ridiculous expressions those girls in porn make, but even still it was justified. His dick was actually very big. The fact that a man with such an impressive cock has been treated this harshly by the women in his age range is a travesty in my opinion. I guess it takes a milf to see the truth.
“It’s not too big is it?” he asked me.
“No… It’s perfect!” I replied as I took him in my mouth. God he even tasted good. At east he had been following my earlier advice on grooming, I never thought I’d be the one to be appreciative of it though. I got his cock nice and wet with my mouth sucking on it, groping his balls and just generally whoring out on it. Even a prim and proper, college educated, middle aged woman likes to act like a slut now and then.
“Oh my God, Ms. Havelock! You do that so well!” he moaned as I sucked him off.
“Please, call me Katie, and let me show you something I can do that those silly little teens can’t.” I replied as I moved up and wrapped my big, soft tits around his long, hard, wet shaft and squeezed them together. Moving them up and down, looking at his eyes the whole time. I almost thought I saw him start to cry as the soft skin of my tits massaged his sensitive cock. I got up further, this time sliding him down the couch so that he’s more so laying than he is sitting, and climbed on top of him fully. I wasted no time in sitting back on his cock, letting it fill my dripping wet pussy. He didn’t even have to finger me or go down on me, I was hot and wet as soon as he sat down. Fuck I needed this so bad. I needed him so bad. Thank God his instincts took over and he knew how to fuck me, cause that would be the biggest shame of all having such an great cock and not knowing how to use it. My hands couldn’t remain still on his body for very long. Him simply charging into my pussy was enough to send pangs of orgasmic pleasure through my body like lightening. I rode him, but his hands held my ass ensuring I slammed down hard on his waist to his liking. Neither of us spoke words, we were to horny, I squeaked and squealed desperately and he moaned under his intensified breathing.
I was never much of a sexual woman back in the day, I had one boyfriend that took my virginity before my husband, but after them I was too busy with work and raising my son to really “sleep around” like other women do. The repressed need for sex in both of us, him only 20 but so intense because of his youth and hormones, and me because I haven’t been fucked in almost 5 years, exploded together in a display of desperate intensity that can’t be captured on porn. We were fucking like a couple reunited after years apart. Like newlyweds that had waited until their wedding to have sex for the first time. In fact, we fucked more closely than I’ve ever been. I was to nervous and too in pain the first time, and my husband was always so bland, but right now we vented our collective frustrations into each other’s bodies. Kissing and groping and grinding and moaning. I probably felt myself orgasm at least a half dozen times before one big one hit. As soon as the big orgasm hit, I sank down deep on his cock and held myself there convulsing as he held me tight to him. He knew as well as I did that I was ok, and not only that, but I wanted more.
Grabbing my waist tight in his arm he slid off the coach onto the floor, sitting down on the rug as I dropped myself repeatedly onto his thick shaft. God damn I couldn’t get enough of this boys cock. I couldn’t believe I was loosing myself so thoroughly to him even though I was on top the entire time. I was a respected therapist, and now I’m on the floor practically masturbating myself with this boy’s cock. Our warm bodies rubbing together as we spent almost no time apart. My nipples I don’t think ever left contact with his chest nor his cock head leaving my pussy since I first sat back on him. I could only grab his head in both arms and pull his face tight into my chest as I rode him like a slut. My pussy tightening around his cock like a vise grip. He moved to the side and laid back, laying flat on the floor now at the foot of the couch as he wrapped his hands around my back. I was still on top, but he was fucking me with the same intensity that I was fucking him. His mix a precum and my juicy wet pussy began to make a mess of our lower regions, filling my office with sounds of gushy, squishy pussy being filled by cock. I had given no thought to how long we had been going at this for. I didn’t really care by this point, in fact I hoped it never ended.
That feeling was solidified in my mind forever when he finally flipped me over on my back, holding my legs back towards me in the air and began to drill my cunt like an oil rig worker. I couldn’t fucking help but scream and squeal as his cock did things to my pussy that nothing before has ever done. Trust me I’ve gotten by with toys at night, but nothing in the world could match this feeling. The longest, hardest most intense orgasm of my life hit me like a train as he fucked me with the longest, hardest, most intense cock.
“Oh fuck Katie! I’m gonna fucking cum!” he grunted out, the first words in so long.
“Don’t you fucking dare pull out you hear me! Fucking fill this Goddamn pussy all the way up! I fucking need this cock in me!” I moaned back. I meant every word. I couldn’t spend another second with his cock deep inside me, I don’t care what the cost might be. I needed him to fill me, and fill me he did. As the last and most extreme orgasm hit, sending my body into a numb, yet electrified state as my pussy lost control and shot out a stream of liquid, squirting all over us both as he emptied his load into the depth of my cunt. He had to tell me to breath again slowly as the orgasm sent me into shock, I was hyperventilating under the pleasure he delivered into me. Rubbing my hair as he held he cock inside me he whispered to me, “Ssh, ssh, breath Katie… Just breath. It’s ok, everything will be ok…” he told me over and over. I saw, as I lay naked beneath him, the rest of my life. I saw no need to ever go on another date with a man, nor let myself be hit on by anyone else. As far as I’m concerned this man on top of me right now is more of a husband than any man I’ll ever meet. The only shame I felt is that I’d never get to bear his children, only the child of my boring, cheating husband.
“Fucking Jesus Christ James! You can never leave me! I fucking needed that! I need it everyday! Please don’t ever go!” I babbled to him as we cuddled on my floor, our naked sweaty bodies drenched in pheromones and the smell of sex.
“That was the best experience of my life Katie! I fucking love you so much!” he replied.
“Listen to me and listen good. If this gets out I’ll lose my license and my job, and may even go to jail. I’m going to write that we had a normal meeting today and that you left saying you didn’t want to continue our meetings. For the next few weeks or so, we have to appear as former doctor-patient, but I mean this with all my heart when I say I want you to be my new husband. I need that cock in me like that every fucking morning before I go to work, and everyday before I go to bed again. I will do every whorish thing you can think of in order for you to stay. things those prissy little bitches you’ve been trying and failing to get won’t dream of doing. What do you say?” I told him.
“I couldn’t think of anything better. There’s no way in hell I’ll ever find a pussy better than this right here.” he replied. Fuck me I was so lucky, and so horny. I got up and with my shaky legs, wobbled into the kitchen and made us some food as the cum and squirt leaked out of my pussy onto the floor. It was 3:45pm, my son wouldn’t be home until 5:30, more than enough time to fuck again…
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Credit to Ava Addams whose the model in the pictures for this story. Hope you all enjoyed
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