Chapter 2: Trish my first

The middle of the fall of my freshman year when I met a most interesting woman. She was standing at my counter where I was checking out her purchases. She asked, "Your name is Matt, right?"

I said, "Yes," looking down at my name tag and smiled. I question, "And your name is?"

She responded with a big smile and reached out to shake my hand, "Trish." I smiled and wondered why the handshake and the wanting to know my name. Trish said, "Are you gay?"

Caught off guard and said. "No, why would you think that?"

Trish said, "I have not seen you with any girls and just wondered if you like guys?"

I replied, "I have a scholarship, a job which does not allow time for other dating."

Trish said, "Too bad you are a good looking guy and someone might find it fun hanging out with you."

During high school, I was a loner. Not having Billy as my friend affected my social development. I decided I did not need any friends. At college, I have talked with several women but did not find them interesting. Compared to the other women I have met, none were as forward as Trish. None had her take-charge attitude. I said, "Trish, are you asking me out on a date?"

She responded with a twinkle in her eye. "Matt you appear different from other men. All they want is sex on the first date. You do give the impression to be safe to date and just have some fun."

I said, "Oh, thank you, I think?"

Trish continued, "I think I would enjoy your company. There is a film festival over at Union Hall you might enjoy. It starts at 8 pm; I will meet you there tonight."

Trish almost directed me to meet her; she was a forward person. I said, "Yes" but did not know why; I was not looking to date but had just said yes. Maybe it was time. My experience with dating women had not succeeded in losing my virginity. I had dreams what it would be like to have sex with a woman. Maybe it was my subconscious making me say yes. I was conflicted; excited about meeting Trish; anxious about what might happen.

Trish smiled as I noted she was a good-looking woman, did not wear much makeup but looked good without the heavy eye shadow. She was five feet six inches and about 130 pounds and dressed in stylish but tasteful clothes. She had pleasant facial features with kind eyes and an intriguing smile. I wondered why she picked me to ask out.

I met her on time at the film festival; we saw two movies and remained for the review. The reviewer was not noteworthy causing Trish grabbed my hand and led me outside. We strolled along the campus talking but not talking about anything in particular. In retrospect, it was a most enjoyable night. I found Trish an interesting person. We ended at Trish's dorm where we shook hands and said good night.

Walking back to my dorm, I found myself smiling. I had a vision of Trish and me making out. My life had been guarded up to this time. I was not seeking a relationship, but maybe it was time for a change. I had to focus and shake those pictures out of my mind.

Because I have six sisters, I understood dating from their view. If you went on a date, and he did not call the next day, then he was not interested in dating again. Therefore, at eight the next morning I called Trish and told her I had a great time. I did not offer her out because if she did not enjoy my company, I rather not am rejected. She said she had a good time also, and she would like to meet and do something different. She did not say what we would do differently but told me to meet her at the student union at 5 pm at the student union.

I hung up the phone thinking Trish was a take-charge woman, somehow appealed to me. We met at the agreed-on time. Dressed in a sweater top and tight-fitting jeans Trish looked casual yet sexy to me. We went to the cafeteria and used our meal ticket to buy our dinner.

Over dinner, Trish told me more about herself and said she was the oldest of six children all boys but her. I told her about my family with me being the youngest of seven all being sisters. We laughed. She said she had to be in command when her mother was away and did it all, washed clothes, cooking, even changing diapers. She complained the toilet seat was always up. She always looked before she sat and was used to having men around the house. I thought she was understanding of her. I did not know why, but I told her because my sisters and my aunt, I constantly sat so the seat was never up. Trish's smile said was fascinating. We continued to compare our families. She said she had seen her brother naked so have seen her share of penises. I remarked the same to seeing my sisters grow up and develop and again; I did not know why, I told Trish for the first six years of my life. I thought I was a girl.

My dorm was coeducational, and lucky I did not have a roommate. Trish asked if she could see my room, and I said sure. The dorm rules said it was OK to have females in your room until ten P.M. then they had to leave. It was now eight P.M., so there was time to sit and chat. We went inside my room; I left the door open as considering Trish might not like being alone in my room with the door shut. She shut the door, walked up to me and without a word, planted my first kiss from a woman. I felt the kiss from my lips to the tip of my cock. We continue to kiss developed to open mouth Frenching as she pushed me to my bed and forced me down. She was on top straddling me. She took off her sweater revealing her purple lace bra. She then kissed me again rubbing her chest against mine as she fumbles with my shirt buttons. I immediately could feel flesh against flesh. After a few minutes of heavy petting and kissing, Trish stood up and with me lying down; she unzipped my pants pulling off my shoes and pants at the same time. I was almost naked with my boxers remaining. She removed her jeans to disclose her matching purple silk panties with lace and bows, which looked similar to the ones I use to wear. She hopped on top again sitting on my crotch rubbing her panties on my boxers when it happened. Without warning, I came; I flooded my boxers with my cream getting someone her panties. Oh God, this was embarrassing. My first time with a woman and I had a premature ejaculation. Trish looked down at my wet boxers and then at me and smiled and said, "My you are a fast squirter." She leaned forward putting all her weight on my body. She continued French my mouth, kiss my neck and lick my ears. I wanted to get up and clean up my mess, but Trish remained on top enjoying feeling the wetness between us. I realized it was the silk undies she wore that made me shoot so quickly. I was with the condition for years to climax quickly when my cock was rubbed with silk panties. How could I tell Trish about my fetish for jacking off with woman clothing?

Trish asked me if this was my first time with a woman, and I embarrassed said "Yes."

Trish said, "Really, I am surprised there were still 19-year-old virgins out there." She continued, "I had been sexually active since I was 16." With a quirky grin on her face she asked, "Matt, do you want me to teach you about having sex with a woman?"

I said softly, "Yes."

Trish's grin turned into a smile. I smile back at Trish. She got up and started to get dressed telling me tomorrow at night at seven pm, she will return. She said she will teach me what I needed to know. But she added, "Matt, one thing you should know, I am in charge, and you will have to follow my instructions, or the agreement is off. Do you understand?

I responded, "Yes Trish, I will be your student."

Trish responds, "Oh, I do not consider a student, more like a passenger in a car; I am the driver; you go where I take us. Just sit back and enjoy the ride."

I said timidly, "Ok." Standing up I wrapped a towel around my body and pulled off my wet boxers, I asked to be excused and what to the showers to clean up. When I returned Trish was dressed and looking at my photograph album showing me with my long curly hair and looking like my sister. She said I was cute, and she liked cute people, and I had been potential. I did not know what she meant by that statement, just responded with an. "Oh."

The next night Trish arrived on time. She asked, "Matt, are you ready to learn about sex?"

I said with a little excitement in my voice, "Yes."

Trish said, "Matt, in any relationship, one person leads and the other follows."

I said, "That makes scene."

Trish continues, "We are not girlfriend and boyfriend and so there is no romantic involvement. We are merely role-playing two parts; I am the woman, and you are the man. I have the experience, so I am leading, and you will follow, understood?"

I nodded my head agreeing and was wondering what I was about to agree on doing.

Trish told me to go take a shower. I was undressed, my back to Trish, I was still shy about having a woman to see my cock. I wrapped a towel around me, went under the shower. I was in the shower just a few seconds when the curtain open, Trish's naked body entered the shower. Trish followed me into the men's showers and entering the shower stall I with me. I wondered if anyone noticed, I were going to get into trouble. She stood in the stream of water; adjust the temperature to her liking. She grabbed the bar of soap, started to wash my face, neck, and chest. She turned me around, washed my back and behind. Reaching around my body, she continued to soap my stomach, and then I felt her hands on my cock and balls. She lathered me up making sure I was clean all over. She handed me the soap and told me to do wash her body.

I started with her face making sure I did not get soap in her eyes. She rinsed her face so she could watch. I did her neck then to her chest. I touched a woman's breast, the first time. Her breasts were firm yet soft. I could feel her body warmth in my hands as I cupped her breasts. They were soft, her skin smooth giving me a flashback to the first time I touch Billy's cock. I did not think about Billy's cock in years. I spent some time holding her breasts, touched her pink nipples, and felt them respond to my touch. It reminded me of when I would touch Billy's cock head, it would get hard when I touched him there.

I moved down and turned Trish around, washed her back subsequently to her firm and round backside. Reaching around, I washed her stomach then down to her crotch. At this point, Trish took my hand and guided my hand and fingers. She leaned back and said, this my clit as she placed my finger on a lump of hard flesh at the top of her slit. This is my pussy as she pushed one of my fingers into her slit. This is my hole as she moved my hand, rubbing my fingers on her hole. Basic anatomy was over. We dried each other off. Trish ordered me to see if the bathroom and the hallway were clear. I checked and motion her to come; she made it all the way to my room without anyone seeing.

In my room, we sat on the bed, removed our towels. I had a hard on. Trish said my cock was impressive and bigger than her brothers were. She said she spied on them and watched them jacking their cocks. She knew all about what boys like to do. Sitting opposite Trish, I kept staring at her firm rounded mounds and her pink hard nipples. She took my hands and moved them to her breasts where she told me how to hold them, not too hard and do not squeeze them, they were sensitive. She said I would get a reaction if I were gentle. She took my finger and placed one at a time in her mouth then my fingers on her nipples. Her nipples immediately responded. She said softly, "Rubbing my nipples can start me to climax, with the right amount of stimulation." She did the same to my breast and nipples and asked me what I felt when she rubbed my nipples. I told her I felt there was a direct connection with the tip of my cock.

Trish said, "Rule number one, I am in charged. Matt you will have to do as I directed, no questions asked. Just do what I tell you. OK."

I thought, "How could I say no?" I was naked on my bed with a naked woman who was telling me what I had to do when she said.

Trish asked, "Matt do you want to touch my breasts?" I reached out to touch them; she slapped my hands. I was shocked. Trish said, "Matt, I did not tell you to touch them. I asked if you wanted to. Now pay attention." Trish continued, "Matt, do you want to touch my breast?"

I responded with a nod, "Yes Trish, please may I touch your breasts?"

Trish said, "Matt, kiss my toes first." She ordered. I did as she told me, kissing each toe, sucking on them and even putting all of them in my mouth. She said, "Matt that was good you can touch my breast now." I did touch and fondle Trish's firm breasts and marveled at how smooth her breast felt in my hand. Trish reached out and grabs my cock. She said, "Matt, I can feel your body anytime and do not have to ask your permission. Your cock does two actions; you pee and you squirt. You are in charge when you pee, and I am responsible when and where shooting. You will do what I tell you to do. You have to ask permission, do you understand?"

I responded, "Yes, Trish." Trish smiled

Trish reached out to touch my cock; the first contact with another human was ecstatic. I could not believe great it felt, and my insides were turning flips. Trish examined my cock and said, "Let's see what we have here. Do you always get this hard?" She reached into your purse and pulled a tape measure. "Let's see, over seven inches long and five inches around. Head cut." "Yes, Matt, you have a lovely cock, much bigger than my brother and bigger than some of the men I have been with." "I would say you are in the top 10% of all men in size of cocks"

Pleased to hear these words from Trish, I blushed. It was wonderful to know you were above average in the manhood department. I did not know how to respond only saying, "Really."

Trish continues her inspections and comments, "You have a lovely size cock; it is straight and in my hands awfully hard. However, you squirt so quickly. We will have to work on that. Now is the best time to start. Do you masturbate yourself often?" As she starts to rub my cock shaft up and down.

"No Trish, I do masturbate often, but only when I am horny and that is only a couple of times a month." I admitted.

"Strange, I would have thought when you came so quick you would be one of those guys who did it three times a day." Trish started to fondle my cock and balls. One hand was holding my balls and the second hand was rubbing my shaft. Trish paused at the tip of my cock, taking the time to use her finger to run around the cock head. I was just about getting used to the pleasant feeling when out of nowhere, wack, wack as Trish slaps my cock and squeezes my balls. I was beginning to squirt, but took the urge out of climax. I showed surprise at Trish's actions. Trish said, "Matt you have a naughty habit of climaxing quickly. I have to break you of that habit. Do you trust me?"

I nodded my head yes. Trish said, "I am going to jack your cock, and I want you to tell me when you can feel yourself getting ready. I will stop and let you calm down. After a few calm minutes, I will start again. Think of something, which is a turn-off to you, something that takes the urge for sex out of your mind." She continued, "What is your turn off for sex?"

Turn off for sex; I had to think about this. I did not think there was anything which was a turn off for sex. Maybe thinking about having sex with Oprah Wimpy. I was not attracted to a black woman. Thinking of her being overweight was the second turn off, the third was here voice. Oprah was a turn off for having sex. I told Trish, "Oprah."

She smiled and said, "Strange you picked a woman to turn you. I thought you might have said having sex with a guy was your turn off. Matt we are going to have to work on your sexual fantasies."

Trish jacked my cock, in less than a minute I said, "OK; I feel like shooting now. She slapped my cock and squeezed my balls harder. She said, "Now think of that black bitch." Which I did and I wanted to climax resided. We did this ten more times, each time Trish treated me the same way. My balls were aching. I had the desire to climax but fighting the urge to climax. I told Trish, "Ok, I am about ready to shoot." Expecting the same abuse as before, I was ready for the slap and ball crushing.