I “lost my virginity” when I chose to have sex, at 19 years old. To some, 19 may seem a bit late. And perhaps it was. But I was never in a hurry to give up my innocence. I never just wanted to get my first time over with. Not only was I a bit scared by the events of my past, but I wanted my first time to be absolutely perfect.
And it was. It was totally magical.
I gave my virginity to a 41 year old man.
You’re probably thinking, ewww! But I can assure you, it was quite the opposite. We’d known each other for over 3 years. When we finally decided to have our first official “date,” I promised myself nothing would happen that night. I wasn’t the type to have sex on a first date. And yet, I found myself shaving and waxing extra carefully the morning before. Maybe somewhere deep inside, I knew he would be the one. I knew I couldn’t resist him.
We met around noon in a hotel parking lot. We had a casual lunch at a quiet restaurant nearby. Afterward we went to a local museum. Then we went back to the hotel. I was a bit nervous as he laid down on the king size bed and said “Come here, Cuddles.” But I laid down next to him and as I began stroking his shirt-clad chest and stomach, I felt completely at ease. I laid my head on his chest and felt his pulse and his breathing. He stroked my hair gently and smiled when I looked at him. I would ask what he was thinking and he would say, “Just how pretty you are….”
That lasted about 30 minutes, but I’d wished it was longer. It felt like 10. But we had to get ready to go. He was a Catholic, so we attended Mass together. Once that was finished, we came back to the hotel again to get ready for dinner. I went into the bathroom while he changed into a dress shirt and pants. I changed into an outfit I’d picked out almost a year ago. Interestingly enough, I’d chosen it specifically with our first date in mind. I guess I always did know it would happen. It was a ruffly, sheer black skirt that came down to about mid thigh. My top was creamy white and felt like smooth, flowing silk. I touched up my makeup and went back into the room. He told me I looked wonderful. I put on a pair of deep purple satin peep-toe pumps. I felt perfect in my classy yet sexy outfit. And he looked amazing too. On the way out the door, a middle-aged woman complimented one of us. He insisted she was talking to me, but I was sure it was meant for him.
It was during dinner that I really started to think about sex. I thought about what would happen when we got back to the hotel for the night. He was 41 years old, but could easily pass for 31. He was very old fashioned, and the most gentlemanly person I’d ever known. He reminded me so much of Cary Grant.
After dinner we stopped at an ice cream shop. He got a vanilla cone and I got a hot fudge sundae to go. Back at the hotel, we watched a sitcom episode. I sat in his lap while he sat in the arm chair. When it was over, we looked at each other. I asked what we were going to do. He must have sensed I was a bit nervous, so he suggested just cuddling on the bed again. I was all for that. We cuddled again in the same position as before. This time though, I kept looking at him expectantly. Finally he rolled me over onto my back, climbed onto me, and kissed me. Passionately. I responded quickly and we were soon sucking each others’ tongues, gasping for breath. He kissed and sucked my neck. I was not shy with him. Still completely clothed, he rubbed his erection up and down along my thigh. I felt very hot. I reached down and un-tucked my shirt from my skirt. He pulled it upward and stared at my bare stomach and my white bra. Then he gently pulled my bra down and began to suck my hard nipples. It felt so great. After just a few minutes, I had an orgasm. He touched my body perfectly.
He began to slide a hand under my skirt and caress my thigh. Then he put his fingers underneath my black satin thong. I felt him tracing my clit and pussy lips. For a second I thought I should tell him to stop. But I didn’t care. It felt too good. Then I remembered I was on my period. I told him, but he just whispered that it was okay. I told him I had a tampon in, but he’d already felt it. We kissed a bit more as he just felt along the outside of my body. Then I went to the bathroom and took out the tampon, and we took a warm bath together in the dark bathroom. We both agreed that the bright lights were not sexy in the least. We sat in the bath together for almost an hour. I sat between his legs, leaning back against his chest. He rested his hands on my breasts.
After the bath, we went back to the bed again. Luckily my period was very light and I didn’t bother putting in a tampon again. He gave me oral sex, not even caring about the traces of blood. I was in heaven. I sucked his cock eagerly. Though I was inexperienced, he was beyond patient. He just smiled down at me the whole time, stroking my hair or pinching my nipple.
He rolled me onto my stomach and lotioned up my little butt. As he did so, I relaxed. Then I noticed a slightly warm feeling inside me. Staying still, I noticed it was inside my butt. Very slowly and carefully, he fingered my butt for several minutes. I almost didn’t want him to stop. But then he climbed on top of me and slid his cock up and down the crack of my butt. Not inside me, just against my smooth skin. I liked it very much. In a few minutes, he ejaculated onto my back. I loved feeling the warm fluid on me. After I tasted it, he wiped it off. It was a strange yet sweet taste.
We did some more oral and fell asleep spooning. I woke around 5:30 the next morning. I turned toward him and felt for his cock in the darkness. It was hard. I put my fingers inside me and rubbed my fluids onto the head of his cock and began stroking. After a few minutes, he was awake too. We took turns using the bathroom and brushing our teeth. Back in bed again, he gave me more oral. That was when I decided I was ready. I told him. And he didn’t even question it. He got up, opened a fresh box of condoms from in his overnight bag and slipped one on.
He teased me, sliding his cock up and down between my pussy lips. Until I begged him. He slid in gently. Though I was very wet and aroused, I was still so tight. My pussy burned slightly with the stretching. But after a few minutes that was gone. He lifted my legs up over my head and went in deep. We both had orgasms. Afterward, he didn’t pull out right away. (By the way, proper use of a condom means withdrawing immediately and throwing away the condom. But I was on birth control pills at the time, so the condom was just an extra precaution) He laid on top of me for a few minutes. Then he got up and wiped himself off with a tissue. I went to use the bathroom and when I came back, I saw him pulling at the sheets. There was quite a large spot of fresh blood on the white sheets. I had completely forgotten about my period. I immediately said I was sorry, but he said he wasn’t bothered. I knew he wouldn’t be; I was more worried about incurring an extra cleaning fee. Somehow blood ended up on the white comforter too, and on a pillow and several towels. He didn’t care.
I gave him oral again, this time feeling his soft penis harden in my warm mouth. When it was fully erect, he got up and rolled on another condom. I climbed on top of him. I suddenly realized I really didn’t know what to do. But he helped me. We kissed and he guided my hips up and down. I was so excited. I had an orgasm within a few minutes. My legs tired and he told me to get on my hands and knees. That’s when he started pounding into me doggie style. It felt so good, I had to try hard to keep from screaming. It didn’t last long. After just a few minutes he ejaculated again. We laid down, him on top of me, his chest against my back. Again, he stayed inside until he began to soften.
Then we showered together. He washed my body and my hair so tenderly. And I washed him in the same way. For quite a while we stood under the hot spray. He closed his eyes while I kissed him and caressed his entire body. I knelt down and began licking his soft penis. I liked how it felt, even when it was soft. I even bit it a little, amazed at how soft and spongy it felt.
We got out and got dressed. As we finished packing up our things, I sat down on the bed and cried silently. He sat next to me right away and handed me a tissue. I threw my arms around him. I didn’t want to go. I wanted to stay with him forever. He rubbed my back and whispered his soothing words. If it hadn’t been almost checkout time, I would have refused to get up. But we had to go. Down at the front desk, the clerk asked him if he’d enjoyed his stay. He gave me a sly smile and said yes. He put my things in my trunk and we hugged goodbye. We kissed again, long and slow. I already knew I couldn’t wait to see him again.
I regret nothing of my first time. Nothing about him being more than double my age felt perverted to me. It still doesn’t. No one has ever treated me better.
I consider myself extremely lucky. My first time was with someone I truly loved. It wasn’t awkward. I wasn’t shy about being naked or touching him. Usual thoughts like, “What if I look fat?” or “What if he doesn’t like what I’m doing?” never came to mind. I felt so sure that it was the right thing. My hymen had broken long ago, so there would be no memories of any pain. He was experienced, so he lasted a long time. Long enough for me to fully enjoy it. And I had a total of 7 orgasms over the course of about 14 hours. Almost all the girls I knew said they didn’t have a single orgasm their first time. Most of them said it was painful and lasted just a few minutes. I had no complaints.
I liked that we did it in the morning instead of at night. Somehow the light of the sunrise gave the whole experience a very pure feeling. And I prefer not to speak of it as “losing” my virginity. Nothing was taken from me. I gave it to him willingly. It was so wonderful. He didn’t mind my inexperience at all. He was always a serious relationship kind of guy. He didn’t believe in one night stands or having sex just to have sex. He was the committed type. I was only his third partner. And I was his first virgin. It had been 6 years since he’d had sex, and so for him, sex felt new all over again.
Later when I asked him his favorite part of our date, he told me it was when I cried before leaving. He told me how much it meant to him that he’d made me so happy. That made me feel special. I’d also cried after the first time we both orgasmed. He told me he’d never known a woman to cry from orgasm before. That made me feel special too.
I would change nothing about my first time. It was more than I could have imagined. But I know that I would be in the minority. Many people have regrets about their first time. Maybe it was the wrong partner, or the wrong time, or something embarrassing happened. So I count myself lucky. It has been burned into my memory forever. I will never forget it.
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