My Journey – The First Time

My Journey…. The First Tim

In high school I was shy, kinda nerdy and studious and did not attract or was certainly unaware of attracting any boy attention. I did look at the boys, the cool or popular ones and think I had no chance of having any of them notice me. Add to this growing up in a Christian house that involved church every Sunday and youth group on Thursdays and the result was I was not exposed to anything racy or overtly sexual. I did hear my parents a few times with some noises coming from their room late when I was sneaking reading a good book however; they never really showed any outward affection aside from a quick kiss hello when dad got home from work. So I left high school a virgin having never been kissed and really having never even touched myself.

At college studying to be a legal secretary (I was not confident enough to apply for law school even though I had always been interested in legal stories and movies), I met my first boyfriend. He was a “nice” boy and had lived a similar high school life as I. We were both inexperienced to say the least lol. We dated and neither of us made much in the way of advances to more contact we were awkward physically and I really only knew the basics. Once he finally got his nerve up to touch me with some petting over my clothes and then slipping hands under I was even more confused. It was ok but not really enjoyable and I was conflicted with my church upbringing. At the end of the school year he was done his course and I was alone again.

Just before my graduation, I was introduced to an older guy through our church and my mother (my future ex husband). I was an old fashioned arranged thing but I thought I was in love for the first time. He was more advanced than I and a lot less shy about sex but it took me time before I could open up such as it was. We were married within a year and I finally lost my virginity at 23 to a man 12 years older. We having regular sex, if you could call it that. Our sessions were him pretty much getting on top, pushing into me and cumming. There was no romance, foreplay, touching, talk or oral to speak off. He was raised more Christian than I was and I think he wanted to rebel but could not really cross the line which left him confused. I was supposed to care for him and bare him children which we tried to do for several years but I was unable to get pregnant and gave up. Eventually he stopped showing me any physical attention, even to snuggle or hold me and we started to drift more apart and my depression started. We finally divorced and I fell into more depression and moved back home with my parents.

While still living with my parents and my mother’s religious overtones I took a job in a small law office working as a secretary to two general practice lawyers. I had not been there long when Frank came into the office. He was running a small diesel repair company and was friends with one of the lawyers. He would drop into the office for work related things and just to visit. When he was there he would always stop at my desk to say hello and I found him pleasant and friendly but did not feel or see anymore than that. One day he showed up and had a coffee for me which he placed on my desk as he walked past. Bringing me coffee and stopping to chat at my desk began to become a normal thing every couple of days for a few weeks and I found myself looking forward to his visits. I was still very awkward socially and especially sexually so I had no idea how to show my new feelings. After a couple of weeks, he asked my out for a coffee after work. We met at a local cafe and had a coffee and chatted about more personal things. He was divorced as well, ran his business but was thinking of selling it and had his own home a bit outside of town. At the end he walked me back to my car and we said goodnight. When I arrived the next morning to work – there was a single rose on my desk. I was shocked – the note said “very nice to get to know you”. We went out for coffee again that Friday – he was gentleman holding the door to the cafe open for me and as I passed placed his hand softly on the small of my back to usher me in. I felt a wave of energy flow through me at his small touch and felt an excitement inside. When I got home I was surprised to find how damp my panties were.

He did not come into the office until late the next week which was making me a bit crazy waiting to see him. I thought about calling him but I did not have it in me to be so forward. When he came in he asked if I would have dinner with him on Friday. I did not hesitate. I was nervous to tell my mother I had a date as I did not need any negativity so I told her I was working late to finish some typing. We had a lovely dinner and then went for a walk together. As we walked he would touch me slightly when he would let me walk in front of him. When we got back to my car the wind was up a bit and blew my hair across my face – he reached up and very gently brushed it back into place – his fingers touching my face as he did it. His hand lingered and he leaned in and kissed me a soft quick kiss and then opened my car door and said good night. He waited a few days to drop by the office again and again I was wanting to see him. We went for dinner again on Friday and then for a walk but this time he took my hand in his as we walked. I had not had a man treat me like this before – tender and showing affection toward me. I blushed and he asked if he made me nervous – I answered yes a little. He stopped and kissed me and it lasted longer than the first one – our lips together right there on the street with people seeing. We circled back to my car and after another kiss he closed the door behind me and I drove home. When I got home my panties were again very damp.

He was amazing at building anticipation and I was thinking about him all the time and even masturbating over him which was something I had never really done since a few times in high school. I was awkward at it and unsure of what really felt good the first few times until I started learning my own body more. We had not even mentioned sex in any of our talking but he had somehow planted the idea in my mind. The dating and office visits continued for a couple of weeks with Frank bringing me coffee and flowers and taking me for walks and dinners. The hand holding, opening doors for me and kisses good night were also the norm. When we walked or nosed around a store together he would slip his arm around me and give me a kiss sometime lingering longer and I could feel people looking some of the time. I would blush and he would wink and smile at me. He was enjoying making me crazy I think as much as I was enjoying the growing feelings I was having but for the most part he was the true gentleman I had always wanted to meet. Finally, one morning after we had been spending time with each other for about six weeks, I found an envelope on my desk when I got to the office. It simply had my name written on the outside in his hand writing. My heart raced with nervousness and excitement as I turned the envelope over and tore it open. The card was a pictures of flowers on the outside and blank on the inside aside from his message – he invited me to come to his house on Friday after work for dinner. I don’t think I had ever smiled so big in my life. I had never had a man cook for me and although I tried to control my excitement I am sure everyone I talked to that day could tell. Friday came and the day seemed to last forever! I told my mother that morning that I was going to be working a bit late and then getting dinner with the law clerk who worked with me. I did not need to hear her scorn for going to a man’s house. I worked a bit late to kill the time before going to his house, locked up the office and drove over. He greeted me with a hug and kiss and then led me into his living room. It was a small house but very neat and organized just like Frank himself. He poured me a glass of wine and then excused himself to see to things in the kitchen. I looked around and the dinning table was set simply with folded napkins and candles. After lighting the candles, he asked me to come sit, pulling out my chair to seat me. I was so nervous waiting there at the table alone before he brought in our plates and joined me. Dinner was great and we chatted easily like we always did. After dinner I went into the kitchen to help with the dishes and clean-up and later we sat on the sofa and he gently put his arm around me and pulled me closer while we chatted. He slipped a hand under my chin and kissed me. It was soft and gentle like all the others we had shared at first but the passion built. The kiss turned into many and our tongues found each other and his hands wove into my hair. I just let it happen – let him kiss me until I felt his hand on my side and moving – he cupped my breast waiting for a protest that did not come. After some kissing and his hands sliding over me pulled back and asked if I was ok.

I told him I was scared and then confided in him my lack of experience with anything more than quick missionary sex with my ex. He smiled and told me we would proceed at my pace and then he kissed me again while touching my cheek so very softly. We kissed more and I was heating up. When we separated I quietly asked him if he would like to go to his bedroom. I was shocked I asked but I was ready to explore more with him.

He led to his room by the hand, pulling me along nervously. My eyes scanned the room – manly decor, black metal bed with a high headboard and lower footboard. He turned taking me in his arms, sensing my nervousness. He kissed me softly reassuringly reminding me to speak up if I wanted to slow down or stop. “Use the word pepper and I will stop emmiately”. It struck me so odd to have a code word but I did not request ion out of naivity. He slowly undressed me without really even looking at me and layed me down on his bed, telling me to lay on my stomach. His hands touched my bare skin for the first time, caressing and massaging my shoulder to help me relax. It felt incredible and I wanted his hands on me more. He touched every inch of my back working lower avoiding my butt to knead the muscles of my legs. Soft moans escaped me as my mind wondered rushing ahead to what he might do to me.

<span;>His hands crept higher again across the insides of my thighs, one making me jump slightly as he started to caress my backside. “Are you ok” he asked looking for my approval which I granted with a week yes. His other hand moved higher between my legs cupping my vagina, his own soft moan liking the wetness he found. “You’re very wet Ms. Casullo” he said with a cones as his finger worked to spread my labia. Feeling me tense he was very gentle working his finger inside me – the first thing to enter me in two years. He whispered in my ear to relax that he would be gentle as he began to move in and out – his lips on my neck and shoulder kissing me till I turned my head and kissed him with a new passion I had never know before. He slipped his hands under my hips and raised me up onto my knees. I felt so incredibly exposed and closed my eyes tightly in an attempt to remain calm and not call out pepper. He moved behind me kissing my butt as he squeezed and spread my cheeks before running his tongue up and down between my cheeks and lower to my pussy – the first time I had been licked there. I was grabbing the sheets and biting the pillow not wanting to scream from excitement and fear. After his tongue worked between my lips and over my clit he had me turn onto my back so I was totally exposed to him from head to toe. I crossed my arms over my chest embarrassed but he reached up and took my wrists and spread my arms pinning them to the mattress. He kissed all around my breasts and nipples before sucking and gently biting my nipples. Finally, he stood and stripped standing at then foot of the bed – I could not believe how hard he was as he crawled back onto the bed and over me – his cock trailing up my leg and he moved between my legs and kissed me as he pushed inside me. He made slow gentle love to me pushing deep in slow rhythmic trusts – his breathing increasing with his lips on mine. I was feeling things I had never felt and was suddenly over come by the first real orgasm I had ever had and then another until he was ready to explode and came inside me. He held me kissing me and caressing my hair till he erectness subsided – I could not believe the wetness that came with him as he slipped out and I loved the feeling of the mess.

We lay together snuggled and kissing softly till it was time for me to dress and head home to my parents.