Katherine is in Charge

Katherine, as she insisted upon being addressed, was a "hard woman" who had the demeanor of a Marine boot camp drill sergeant; a "no nonsense" approach to her career which was that of a mental health professional. I guessed her age to be mid 50s or so. Was her attitude a good approach to someone whose career it was to help people adjust to what had happened in their past and how to move ahead with life's newest obstacles and challenges??? After my first two sessions with her I wondered.

I did pay some attention to Katherine's body; she had extra padding in all the right places; her chest was neither small nor was she overly buxom; they were of a size I could easily hold onto and massage if given the opportunity. Her backside bottom swayed nicely and enticingly enough that I fantasized about doing her doggie style just to feel and watch my boner slide in and out of her. She dressed in such a way as to not bring attention to her body and physical assets. I wondered too...was it a "pussy" or a "cunt" between her thighs?

I could not challenge her thoroughness nor her ability to dig deeply into my past. We talked at length about my frustrations and challenges; I never met a breast I did not want to have fun with nor a nipple I did not want to suckle like the Energizer bunny; my lack of self confidence with women...because I had average looks and more because I was less than average size.

Katherine asked me about my physical experiences with women, so I began by telling her about Jeanne who was six years older than me. I lived with my parents on the second floor of an old four flat apartment building that relatives owned. One summer afternoon after my sophomore year of college I was leaning over the second floor railing when down below appeared this red head with an abundantly buxom bosom. Instant boner! When Jeanne walked anywhere her bosom got there ahead of the rest of her. I had to find a way to get a better look! During winter break, shortly after my 19^th b-day, I made up an excuse to visit Jeanne; her man had gotten her a puppy for Christmas. We sat at the kitchen table while we made small talk and I played with the puppy. Just as I was leaving I reached out and squeezed Jeanne's breasts with my hands and asked her if they were real? Her reply was "Come back around noon tomorrow." When I knocked ever so lightly on her door the following day, she opened it barely enough to let me in then locked the door shut immediately after. She greeted me in bare feet and wearing a sheer yellow mid thigh teddy and matching sheer yellow panties. We went to the one bedroom where she had been watching TV. The irony of it all was that she had a show on and the highlight of the show was the Grand Prize Game. I sat on the bed next to her and after a few awkward moments she took off her teddy. "Are these what you wanted to see?" They were amazing. I don't recall their exact size, all I remember is that each breast was more than a wonderful handful; my first time seeing and touching bare breasts. I was in heaven; my brain had turned to mush. I had what I wanted...her breasts; Jeanne had other plans.

After a few minutes of having her breasts fondled and massaged and played with, she asked if I wanted to see more. HUH? Did I hear what I thought I had heard? Off came her panties, she got comfortable on the bed and spread her thighs apart. I got on my knees on the floor in front of the bed, forgot about her breasts and got my face so close to her that I could inhale her scent. I knew nothing about cunnilingus then. DARN! That is when I got the real surprise, she asked me if I wanted to try putting it in her. I had never seen a pussy in person before that afternoon, let alone got invited to go all the way. My head was spinning; I was soooooo nervous; I could not get my clothes off quickly enough. My inexperience was my downfall; I could not get it done. At least Jeanne was the first woman to handle my package. Because of all that happened that afternoon, I explained to Katherine that Jeanne is the one woman from my past that I would like to have met again later and had a one on one talk with, simply to understand her motivation for doing what she had done. I wanted to play with her breasts; she wanted my virginity. Because she was two to three months pregnant at the time, Jeanne was OK with my being bareback and depositing my seed in her body. What I wondered about and noted to Katherine also...if Jeanne was OK with me depositing my seed in her, were there others with whom she had made the same choice???

Katherine got me to talk about my adult frustrations. I told her I had been satisfied and content except for one constant nagging matter; I had become focused on wanting to explore oral sex and whenever I had asked my partner to take me in her mouth, playtime ended immediately and did not happen for sometimes a week after. My partner had no desire to take me in her mouth, no matter how much I asked and begged and even tried to bribe her, let alone let me cum in her mouth. She probably would have gone back to her mother had I cum in her mouth, she was that opposed to giving me oral pleasure. That frustration kept getting more difficult to deal with; I was over 40 years old by this time and had never experienced oral pleasure of any kind. I made the selfish decision to find a woman who would take me in her mouth even if that is all she did, taste me. I did not expect her to let me cum in her mouth and swallow my seed. That is when I connected with a married couple a few hours drive from where I lived. She was willing to take me in her mouth; not let me cum in her mouth. She was a couple years older than me and had a great chest. She was an X-ray tech at a local hospital; he was an EMT. They were into the swinger lifestyle years before the Internet came into existence. I was both eager and nervous.

The outcome, as I explained to Katherine, was not what I ever could have anticipated. I could have had Dee Anne bareback a half a dozen times at least yet it bothered me finding out how many men and couples they had played with without protection and at a time when AIDS was starting to get out of control. I learned a very hard life lesson from knowing that married couple...not everything is what it seems, and all the thrill and fun and games can come at a cost, a cost that one cannot undo and can change lives forever. The wife played along with the swinger lifestyle just so she could attract a "chivalrous knight" with whom she could ride off to start a new life of her own. I got way too emotionally involved with her to the point it nearly ruined my life in ways that never could have been undone. Lesson learned...never get so involved just for breasts and physical pleasure that you cannot walk away and minimize the hurt of the connection made. It took me several years to get over my relationship with that swinger woman. After that, if I got involved with another woman for pleasure purposes my emotional investment was shallow at best.

I shared my involvement with a single mom and with a gorgeous nurse who was also a regional supervisor for the nursing department of the state she lived in during another therapy session.

The older single mom took what the swinger woman had done but went all the way; she introduced me to amazing oral pleasure, twice. I was her late night snack and her breakfast treat. Guess how it felt to get woken up by a woman who is trying to suck out my brains through my cock? She drained me in more ways than just giving me oral pleasure and she licked me clean; my legs were like rubber when I left St Louis; I had to stop at a rest area and take a nap. She was soooooo good at sucking cock, she could have given lessons, and she amazed me by suckling her own nipples. OH MY!!!

The nurse, around 50 years young, on a scale of one to ten she was between an eight and a nine when it came to her looks. She was "out of my league" as the saying goes. She might have been higher maintenance as well? What she did introduce me to was cunnilingus. When we got back to my hotel room and, after she got done teasing me about her pierced nipples and flirting, she undressed, got comfortable and said in a very "I'm the one in charge" manner...."Eat my pussy!" I had never tasted pussy before. My reward for eating her, she sucked me off and swallowed my entire load. I called her a week or so later, her husband answered the phone and told me never to contact her again. HUH??? That raised all kinds of questions in my mind. They had presented themselves as experienced swingers who played together and played alone. I had to wonder if this nurse had met me without telling her husband what she was going to do???

After two sessions I began to wonder what Katherine was doing with all the very personal data I was sharing. In ways I felt a catharsis, a cleansing of my mind and soul during and after each "confession". What I didn't reveal to her was that sharing all this was also stimulating. In a way I felt she was like a voyeur??? She asked about any emotional involvement with those ladies and I admitted that there always was some; that I was not wired to just get it up and have sex like you see in porn videos. I made it a point to never get involved with more than one woman at a time. I was interested in knowing some of each woman's story especially because all of them were older than me and most all were attached and not getting much or any attention at home. A couple of them revealed that they felt emotionally abused by their life partners. One in particular was a 67 year old grandmother who craved affection more than sex. To get to first base with her I had to hug and kiss her and make her feel genuinely wanted and desired. I guess I made a good first impression; the first time we met, in a Walmart parking lot, after a while she discreetly undid part of her top and offered me one of her breasts. I had never seen nor touched such a gorgeous mound before, she told me her bra size was a 48E and had been as large as 52E. WOW! It took two hands to caress just one of her beauties. I did appreciate the opportunity to see and play gently with her breast and gave her nipple some attention. I could tell that she was enjoying the contact as well because her bud was getting more and more erect and when we kissed our kisses were lasting longer and longer. Next time we met I got to taste her nipples. She invited me to come for a visit, she had a place she could host. Whenever we got together I would greet her with a kiss, kiss her with passion and desire and give her breasts a nice squeeze; I wanted her to feel good being with me. The few times she hosted, we got into bed and she would let me suckle all I wanted as long as she got plenty of kisses.

Like every woman before and after, whose breasts I got to have fun with, they helped themselves. My small sized package did not seem to matter; they wanted to at least touch and feel and play with me down there; I was happy to let them have their way and I never disappointed, I ejaculated for all of them at least one time every date. A few of them especially liked to play and watch and found it stimulating when they popped my cork. None of these flings ever lasted more than a few months with one exception and that affair went on for nearly three years until we almost got busted by her neighbor who happened to be driving through the same park where we were meeting. This same woman, also a new grandmother, wanted to feel physically desired and I was happy to oblige her. She had a fun naughty side. One fall afternoon we met up at a state park and walked one of its trails. The park was empty. We were out by the lake overflow dam; she was leaning on the railing; I was directly behind her giving her blue jeans covered ass some groping; then started to dry hump her from behind. She in turn pushed back against my bumping and grinding. We continued our walk and I continued to playfully grope her ass. Along the trail she abruptly stopped, turned to face me, put her hand into my sweat pants and proceeded to fondle me until my knees buckled because I had made a sticky creamy mess in my boxers. She gave me a big satisfying smile. I nearly ended up on the ground my climax was that strong. When we could arrange it we would share the cost of a room for naptime; that was back when some motels had short stay rates. We would be barely modest for naptime; both of us wore thongs that did not cover much but that is what we wanted. She loved baring her breasts and her juicy thick nipples; she was not shy about taking off her thong and exposing herself for me. I would do the same for her. She loved touching and playing with my package and especially enjoyed making me climax, sometimes twice in one naptime session. One particular afternoon we were really trying to nap, we were cuddled up close. She was free to touch me anytime and it was not unusual for her to undress me then have her way with me with her hands. I felt her remove my boxers and start playing; then she caught me completely by surprise. I was not erect yet but she put a lip lock on me and started to suck. All of a sudden I was wide awake; I looked down at her just as I came in her mouth; she swallowed my load, licked me clean and smiled. It was her first time sucking me off although she had talked about doing me orally several times before. It felt so good mostly because we had been seeing each other for almost two years by then. I wish she had sucked me off more than once.

Katherine spent almost one whole session listening and asking about feelings and more when we talked about my brief fling with a retired social worker. Colleen was a sweet Irish Catholic who had raised five children by herself, her husband had run off with his secretary. Colleen was 66 when we connected, ten months older than me. I liked our age difference because we had grown up at the same time so had lots in common that we could have good conversations. She also had lots grandkids; she loved talking about them and showing me pictures; this made time together pleasant and interesting for both of us.

I explained to the therapist that my involvement with this particular grandmother was unique in a lot of ways. First, the lady had not been on a date with a man in over twenty years, so she had not had any physical contact with any man either. When we connected it was like she started going thru puberty all over again; she was nervous and self conscious about her appearance. At one point she called and started to cry; she knew I liked breasts and she was depressed that I would reject her just because she had had a boob job and her 38Ds were not natural. I took my time and as calmly as possible talked her "off the ledge" and did my best to convince her that everything would work out. When we finally did meet in person for lunch, we spent an hour or so at a park just getting acquainted. Her favorite phrase was "Hugs and Kisses, OH MY," so I hugged her and we kissed a little to "break the ice." We had a large blanket wrapped around ourselves for both privacy and warmth; that is when she did something I never expected; she slipped my hand inside her coat and under her sweater; next thing I felt was one of her nipples, perky and erect, poking the palm of my hand. It was such a nice thing on her part; I made sure she knew how much I enjoyed that little bit of intimacy.

me back to our booth flushed in the face because she had walked into the MENS room instead of the LADIES room. Was she nervous or what??? There was so much to like and look forward to spending time with this lady; she wanted a man in her life now and she wanted both emotional pleasure and physical pleasure. When we finally got to spend an entire day and night together she let her libido take over; she wanted physical pleasure as much as if not more than emotional pleasure; she was down to only her panties and ready to take them off as well not long after we got to our suite when I gently suggested she relax and slow down, that we had the rest of the evening and night ahead of us. I am not sure I hurt her feelings suggesting she take it easy. Eventually she wanted me to come down to her apartment; she wanted us to spend a couple of days and nights getting a whole lot more acquainted; her ultimate intent was that we would consummate our friendship in her bed. She also hinted that when we might be out for a ride together she might not be wearing any underwear; that we might find a discreet location to park and she might just expose herself. I confessed to the therapist that even years later I still got aroused thinking about this particular grandmother; that this grandmother was the first woman I was with whose pubic hair was the same color as the hair on her head which was a gorgeous silver gray; that this grandmother was so tight I had to be careful easing two fingers into her. I dreamed how it would feel to have my erection in her and have her squeeze me like a vise with her body.

It was at this point Katherine put down her notes, asked me to step over where she was seated, which I did, not knowing why nor questioning why; after all she was a professional doing what she was trained to do. Katherine looked at me directly then asked "Are you stimulated in any way simply talking to me about these particular events in your life?" I did not verbalize my response but knew she knew the answer. She reached out with her hand and placed it on the front of my pants; her touch made me nearly pop my cork. "Let me see" she said, in a way that sounded more like a command than a request. I obeyed her and shortly my pants were down around my ankles. She immediately noticed the small wet spot on the front of my briefs; she took her index finger, touched the wet spot then pushed against it. My knees nearly buckled. "I want to see more" she commanded. She hooked her fingers on the waist band of my briefs and tugged them down past my knees. I was both embarrassed and aroused at the same time; embarrassed because of my size; aroused because the tip was glistening with precum.

She looked into my eyes, "So this is the source of so many of your feelings of inadequacy?" I said nothing, too embarrassed to talk. She gently touched the tip of the head where another drop of precum was glistening; she spread the drop around. I closed my eyes tightly and willed myself not to pop my cork, at least not yet. She moved her attention away from the head to my sack which she cupped with her hand and massaged. I was relieved she had stopped touching the head. I spread my thighs so she could feel me better. She said nothing, just fondled me for a while. I rested my hands on her shoulders to steady myself. Was I being "molested" by my therapist? Was this right? Was this professional? I was not the one who started this, she did. Silently I asked myself these question; yet I did nothing to stop her. Was I giving my consent by not objecting?

There was a long pause, just long enough for me to feel a slight chill on my exposed package; that chill caused my cock to shrink and withdraw. Katherine took matters into her own hands. She pinched her thumb and index finger on the loose skin and pushed back, exposing the head fully. With her other hand she pressed the base of my cock against my pubic mound and tried to stretch my shaft to its full length. I was aroused but not yet erect. Her touches and caresses and fondles made my knees weaken again. She squeezed the base of my shaft and made my semi flaccid shaft flail around and waggle. I was glad she had stopped touching the head; I was way too close to popping off...again. She seemed to take delight in waggling my semi hard shaft, making my cock wave around. Done with making me waggle, she took to carefully examining the shaft and head of my cock, especially the head. Her fingers expertly touched and caressed every part, paying special attention to the rim and the opening that was leaking another drop of precum which again she spread all over the head.