Tiffany's Ultimate Prize - Pt. 01

Or how I got pregnant

Greetings, one and all. I have decided to tell you about my life and all its little secrets.

This story takes place in the early 1960s in Massachusetts. The Comstock Act and Puritanical laws at that time made disseminating Birth Control information or devices to unmarried individuals a serious crime. You can Google it if you need to.

Firstly I want to give you my details so that you can picture me in your mind. I am five foot 4, have green eyes, and am slender with long legs. I have red hair. It is the color of a newly minted penny. My hair is currently in a tight ringlet style about mid-back length. My white skin is covered with a million freckles. My B cup breasts have half-dollar-sized aerolas and always perky nipples that have a brick red coloring. I have very pronounced Montgomery glands. I later learned that men called nipples like these "Puffies".

I never wanted more up top. My breasts suited me and my overall shape. When I was eighteen I learned that a hot shower on my breasts and especially the nipples would get my vagina wet and ready for play when I went to bed. I hope that with this information, you can visualize me.

My mother passed on her version of the "Birds and Bees" three separate times, once at twelve, then at fifteen, and the final one at eighteen. It was the "Protect yourself and don't get pregnant speech."

I was popular in school and never lacked a date for any function or event.

After graduation, I worked at the local Burger joint, where I met Lenny, the cook. We started dating quite a bit. Our dates became increasingly intimate, longer, and more steamy.

After six or so dates, I was ready for the big deed. I was prepared to go all the way, and when he produced a rubber that he stole from his father's dresser, I knew I was about to become a woman.

After work, Lenny picked me up in his dad's 1963 station wagon. The back seats were folded, and I saw several sleeping bags. My panties were getting wetter by the minute as we drove out to Lover's Lane.

I wanted this to happen as much as he did. Tired of necking and fingering or rubbing each other at the movies only to have to go home and masturbate silently in my room so that my parents would not hear me through the wall.

My first time was not what I had expected. Although there was lots of passionate kissing and groping, the thrill of actually getting naked in the car was like a line to be crossed. I waited for him to put the rubber on, and he asked me if I was sure I wanted to do it.. I nodded my head and pulled my knees up and spread myself wide for him. Lenny mounted me and thrust several times missing my vagina completly. I had to reach between us and told him to be still as I guided him to the appropriate location. "Slow, Lenny, slow." His warm rock hard cock sank into me. The feeling of fullness was incredible. There was just a bit of pain as that was the largest object ever inside me.

Lenny bottomed out, and it was about ten strokes when he moaned in my ear, "AHHHH, Tiffany, OH MY God". He withdrew and, still kneeling between my splayed legs, stripped the rubber off and tied it in a knot. Then he threw himself down beside me.

We dressed without another word until we returned to my house, where he said, "I am ready to do it again. Let's go steady. I will get another rubber tomorrow."

I felt down and mumbled, "Ok, see ya."

Dad was up, and I tried to sneak up the stairs, but he called me down. "Tif, are you still hanging with that useless Lenny character? He's nineteen going on twenty and still flipping burgers. When is he going to step up and get a real job? I still can't see what you see in him. All he has to do is ask, and I will get him on at the shipyard."

"Ok, dad, I will tell him that. Good night."

"You too, sweetie." and he kissed my forehead.

My panties were soaked, and I dropped them in the bathroom and kicked them into the corner. There was just a trace of blood when I wiped. I ran the shower hot and tried to relax. I allowed the hot water to prick my breasts and nipples for a long time slowly reawakening the tingling in my pussy. I was still aroused and getting more so now as I recalled the events of an hour ago. I put in a tampon just to be safe and went to bed. Spreading my legs and pulling up my knees was almost an automatic response. I had a glorious orgasm by rubbing my clitoris and pinching my left nipple hard at the same time.

The next day, Lenny got me in the storeroom. "Listen, babe, I went to buy us some rubbers this morning, and Mr. Polinski has them behind the counter, and you gotta ask him for them. I can't because he and my dad are good friends. I got us one more for tonight. See if your dad has any when you can."

I said, "No, Mom still uses the diaphragm, but I might be able to buy some jelly closer to Boston where they don't know us. Let's go on Saturday morning." Lenny pushed me against the wall, crushing my breasts into him, and we parted with a deep tongue thrusting kiss that made my pelvis throb.

As I was getting ready to go out that night, Dad asked me if I had asked Lenny 'The Question. I said, "No, but I will tonight." He gave me the stink eye and shook his head.

When we settled in together, I told Lenny we needed to go slower, but the results were about the same. That night, we cuddled, and when he rose to the occasion about twenty minutes later, I was still so aroused, but I did see that the rubber was still on as I guided him into myself. Well, he was able to last and last, and his thrusts became heavier, and I was climbing the ladder to my orgasm. It hit me, and I screamed out. That scared him, and he stopped deep inside me. My vagina spasmed and that brought him off as well. When he withdrew he said "Oh shit, wheres the fucking rubber?" As he flopped over beside me I distinctly remembered seeing his penis wilting and wet in the moonlight. I reached down and was hoping that it was on the outside, but there was nothing but a considerable amount of wetness on my vulva. "Take me home NOW," I screamed at him.

When I got in, Mom and Dad were watching the news. Mom inquired, "Is everything alright? You are in early." I said, "Yes, Mom," and rushed to the bathroom.

I stripped off my skirt, which was full of the evidence of my transgression, and sat on the toilet. I franticly dug in my vagina with two fingers and finally felt the rubber up against my cervix. I cried as I dropped it in the bowl and flushed it away.

I was torn between asking Mom for help and praying that I would be spared the wrath of my parents.

Our Saturday junket was not a happy time. We were rejected at the first three pharmacies we stopped at. Lenny was red-faced and nervous when he left the car. One older man asked him if he knew what they were used for and laughed in his face. He was getting frustrated and told me to get the jelly I discussed at the next one. Well, I saw it on the shelf but froze up when it came time to face the pharmacist to pay. Ultimately, we never needed to worry about getting pregnant because...

Eight weeks later, I was at the gynecologist's office and holding my mother's hand as I submitted to the pelvic exam. I had to answer all the questions about my last period and the suspected date of the 'mishap'.

I cried during the internal exam, not from pain but from embarrassment. My mother ever the stern one told me to suck it up, that this was only the beginning.

A week later, the tests confirmed that I was with child, as they used to say back then.

My father exploded. He ranted, raved for hours, and then demanded that I tell him where Lenny lived.

He returned several hours later and calmly told me my husband would start at the shipyard in a week.

Following that, he never spoke directly to me again, always using my mother as a relay.

We were never allowed to spend time alone until our wedding night, a quick and quiet affair at the V. F. W. with just the required people.

No flowers, my old prom gown, and a homemade cake. It was over in thirty minutes.

Mom had paid for a motel in the next town for our Honeymoon. We had sex like never before, naked all over the room without a care in the world. No rubbers are needed.

After our third attempt, we both fell asleep. I was sore and had difficulty walking the following day, but I was happy--or so I thought.

Lenny started talking about how we would skip town and get an apartment now that he was making good money. I told him that it was crazy talk and that we would be together in my room for a while.

Lenny did not adapt to life at the shipyard very well. The first week, he made only a few dollars because they took all the safety gear out of his check. The work as a grinder was hot, heavy, and dirty, and having my father as his boss and having to live with him in the same house weighed on him. He was afraid of heights and came home exhausted.

Living headboard-to-headboard also dampened our sex life to almost zero as I could not get into it with my parents listening to our exploits.

I, on the other hand, was going through all the hormonal changes related to pregnancy. Breast size increased, I was wetter and needed to get off more than ever, Mom made me read many books and pamphlets that explained all the changes. The breasts were even more sensitive than before, and the cup size increase meant new bras and maternity clothes.

As summer turned to winter, the belly protruded well as I entered my seventh month. All tests were routine, but our positions for sex had to change when we had it. I was much more comfortable being entered from behind. I loved it when Lenny grabbed my hips and slammed into me. We had become proficient in having silent sex, which was not an easy task.

One Saturday, Lenny drove me and Mom to an O. B. appointment during my eighth month. He was terrified, sitting next to me in a waiting room full of pregnant women, so much so that he was sweating. I was trying to show him the large book that illustrated what was happening inside me. Then I flipped the page to the delivery sequence. That is when Lenny bolted from the office.

He stole the car, which was recovered in Albany, New York, with an empty gas tank.