Where it happened: College
I can’t believe that I’m going to write about this. I came across your site by accident and I loved reading the entries. For a about three days I couldn’t get ‘my first time’ out of my head and all of the wonderful times we had leading up to that moment. So here goes, I hope those who read it enjoy! Sorry, it seems kinda long.
I’m 36 years old and I lost my virginity just 4 days after my 18th birthday. I had been dating this wonderful girl (Elizabeth) who was my first real girl friend and also a virgin at the time. I married her about 4 years later.
I met Elizabeth in the restaurant where we both worked (we were 17) and we hit it off right from the start. She was preppy (wore Izodd Polo shirts, plaid skirts and sweaters and generally shopped at LL Bean) and had a great figure. Long slender legs, a rear that melded into her thighs, tight stomach and chest that was just right (later learned she was a sweet 34C) a wonderful smile and a great head of light brown hair. She weighed around 110 lb. and was 5′-8″ tall. She came from a good family on the ‘right’ side of the tracks. As for me, I guess I was from the other side. I on the other hand was the Bruce Springsteen type but, very quiet. T-shirts and jeans. I was fairly muscular and slim 5′-10″ tall and weighed about 160 lb. with longer brown hair. Since I will be telling you some of my most intimate secrets, my cock was a respectable 7-1/2 inches (still is) and I has slight body hair and that includes in my pants.
As I said, we met in a restaurant and I couldn’t take my eyes off of her. After a short while we started to go out on dates and fairly quickly turned into an item. She had the use of her parents car and would always drive me home late at night after work. We would stay up most of the night talking about ‘stuff’ and eventually began to make out. Nothing big, we were slow starters as neither of really knew what to do. Basically for many weeks that summer it was mostly talking, kissing and caressing, didn’t even include any of the good stuff. One evening we were sitting on the steps in the back yard and while we were kissing she put my hand on her chest. I was stunned! I had never felt a girl’s breast before and I immediately began to caress and massage it as we kissed. I still can remember the feel of her hard nipple through her shirt and bra! My dick was as hard as a rock. But, nothing happened. I stayed on the outside of her shirt and she never touched or entered my pants.
After the ice was broken and we began to experiment more but, still never really went very far. That summer was great but, I’ll skip to the week before we had sex for the first time. (I wish this site had a section for other sexual moments because this is fun to do and I have some great stories to tell!)
Anyway, later that summer, we both went away to college and we were very sad to see the other go but, swore that we would stay in touch. And we did!
In college we were only a few states away and we managed nicely between bus trips and phone calls. When I was there (about every three weeks) we seemed to have developed wonderful closeness and very open with each other about sex and nudity (partial). Again we were slow to start. You’d think that two horny kids away from home would be going at it like rabbits but, not us. We took it slow and until later in the year did we even take off our pants in front of each other. Here’s a story that leads up to our ‘first time.’
At college, Elizabeth had developed a very good friend in her roommate named Susan who, I believe was coaching her in the art of sex. Susan was very experienced, good looking with a great figure and larger breasts than Elizabeth’s and would basically screw anything in site. Anytime I was there she would always be talking about sex. Everything from her escapades (which were numerous to say the least) to how she liked to ‘get herself off.’ At first it was embarrassing since she would always make ‘cock’ jokes at my expense and try to cop a feel. After a while I seemed to get used to it. Susan’s jokes actually seemed to loosen up Elizabeth and me. Eventually Elizabeth and me were rolling around in bed with me in my briefs and her in her panties grinding ourselves to orgasm and making out to almost the point of getting naked and really doing it (Susan was hardly ever in her room). Also, for some reason we all three of us became VERY close friends and started to be much more comfortable with each other. Partial nudity (bras, panties and briefs) became fairly common place. Then all of a sudden, Susan started in with virgin jokes all of the time. She knew about Elizabeth and me being virgins and was trying to coax us into our first experience. Perhaps she thought enough was enough. I’m sure that when I left from my weekend visit all of the details were shared and advice started to flow.
On one visit, we all chipped in for a bottle of wine. It was a pretty big bottle and after a short while we were all fairly drunk. Susan made the suggestion that we play strip poker. She also said that we would be no nudity since there were virgins in the room. I think both Elizabeth and I took offense so we took her up on her idea. After almost an hour I was down to my briefs. Elizabeth still had her top, bra and panties on. As for Susan she was down to a skimpy bra (fairly see through!)and panties. The next hand had Elizabeth’s top off. I was very hard and my briefs were standing up like a tent but, I didn’t care! With more wine were now all very drunk and the last hand needed to be played. To my amazement Susan lost! She stated said, ‘change of rules,’ and since she was not a VIRGIN, removed her top. She reached up and pulled open the front of her bra letting her gorgeous tities spill out. She had large areola and thick nipples. I almost came right there, but there was more! She dared Elizabeth to do the and started in on how I liked to suck on ’em. Elizabeth removed her top!! With that, Susan said nothing, stood up and pulled her very wet panties down and stepped out of them. She was totally naked! She had a very wet, nicely trimmed, light brown pussy looking me right in the face. She said, ‘top that!!’ to us both. Elizabeth and I couldn’t, as I guess it was a bit too much for us at that point. We had never even seen each other totally naked and were not about to start with Susan in the room. Well, she kept taunting us!! She would say things like, ‘Oh, common little virgins, get naked, you have to start somewhere,’ ‘show me that virgin cock, and I’ll show Elizabeth how to make you spurt!’ After a bit, and no response from us, she went to her closet, bent way over exposing her backside and pulled out a dildo, sat on the floor laying back against her bed saying, ‘Here, I’ll show you how it’s done.’ She proceeded to slide the rubber dick between her wet lips lubing it up while telling us how it felt and that we should, ‘get naked cause your missing all the fun!’ Then she opened her legs even wider, parted her lips with her fingers and slowly slid the dick inside until it almost disappeared! I started rubbing my cock through my briefs and I glanced over at Elizabeth and she was mesmerized! Susan then closed her eyes, stopped talking and worked herself a little faster while rubbing her clit! All of a sudden her legs came together and stretched out with the dildo deep inside as she let out a sexy low Ohhhhhhhummmmm and passed out on the floor! The dildo was still between her legs.
Elizabeth and I looked at each other, and I guess we thought she was OK because we covered her up (leaving the dildo where it was!) at the side of the bed. Then we quickly dropped our underwear and fell into bed! I was like magic and that we seemed to know exactly what to do. Elizabeth seemed to know more than me and I remember thinking that perhaps Susan told her what to do or perhaps it was all the times we read Penthouse’s Forum letters and caressed each other while reading. We started with some real heavy, deep kissing and our hands were flying everywhere! I remember Elizabeth kissing me down my chest and down towards my hard cock. She proceeded to kiss and lick my inner thighs and just under my balls. Then she slowly kissed and licked her way up my balls and then up my shaft and circled the tip with her tongue licking some pre-cum out of my hole. Then, for a bit she took my tip between her lips and rolled it and played. I remember feeling her spit sliding down the shaft and through my ass. Then she slid the whole thing in and slowly worked her head up and down!! Oh, the feeling was priceless!!!! My first blow job!! All this time she was laying next to me and I was trying to prod her into a 69 position, finally she flung her leg over and stuck her little tan pussy square into my face! The lips of her pussy were long and folded like the petals on a rose (now my favorite flower) and I could clearly see her puckered little ass. I started licking everything in sight! I loved to watch her squirm and listened to her moans of delight! I noticed earlier that Elizabeth’s panties were soaked and now juices were literally dripping from her pussy and covering my chest. I loved to spread her open and stick my tongue deep in her hole. As I did the tip of my nose would nestle in her ass hole. The taste of her was so exquisite! She seemed to like everything I was doing and I loved her lips around my cock. After a bit she started to buck her hips and grind her pussy into my face when she let out a fairly loud aaaaahhhhhh!!!!!! I was also about to come and I think she sensed it I since started to buck my hips a bit faster. I told her I was about to shoot my load in case she didn’t want it in her mouth, and she stopped sucking and she maneuvered me so I on top of her so my dick was between her cleavage. We quickly lubed her cleavage and I started to hump feverishly! It wasn’t long before I shot all over her neck, chin and hair!! We were both sweaty and reeking of sex and fell fast a sleep in each other’s arms. When we awoke the next morning we were both laying on top of the sheets naked and Susan was gone. That afternoon we talked with Susan about the previous nightÃ¢â‚¬Â¦but, that’s another story.
The next weekend I came back to Elizabeth’s college earlier than I would have normally simply to actually do it!! All that week we spoke on the phone about why’s and how’s of us having sex. We spoke very intimately about the topic which went easier and nicer than I ever thought possible (it was also hard to do since I shared a dorm room). The whole thing brought us even closer since it proved to us both that we cared for each other very much. I was so embarrassed when I bought my first box of condoms.
That week went so slowly when I could actually hop on a bus to get to her. She met me at the bus stop and had such a great smile and kiss. I noticed she wasn’t wearing a bra! That day we prepared the room with candles, perfumes, low lights, music, set the window blinds, added pillows and towels to the bed, etc. and oh yes, the birth control! I had my condoms and she had purchased some sperm-acide gel that she needed an applicator for. Next we headed for a very romantic dinnerÃ¢â‚¬Â¦. at the college cafeteria. After dinner we headed straight back to her room. On the way we ran into Susan. I guess Elizabeth had told her about our planned evening. I was embarrassed, but Susan gave us both kisses and a bottle of wine. She apologized again for the prior evening and said to enjoy ourselves and told me to specifically to take it slow. I smiled and was pretty flushed.
Well when we got back to the room, we opened the bottle of wine and quickly drank half of it. We turned the lights down, lit the candles and looked into each others eyes saying, ‘I Love You’ to the other. Standing there next to the bed we began to kiss. Our tongues probed deeply into the others warm mouth. I gently unbuttoned her shirt and let fall off of her shoulders. I turned my attentions to her shoulders and to the top of her beautiful breasts. I was excited and nervous at the same time. I wanted her so badly! I placed my hands on her chest, feeling her warm globes and then began to lick and suck on her nipples. Elizabeth slowly worked off my shirt and began to caress my chest and back. She had her hands in my hair, and was pushing my head farther down on her breasts. Elizabeth’s hands reached down and unbuttoned my jeans. I gave her a warm smile. Elizabeth bent down and slide my pants slowly down my legs and helped me step out of them. All I was wearing a pair of briefs and I was very hard! I turned to help Elizabeth out of her pants as she did me and I saw that her panties were just about soaked. With that I lifted her to the bed. We kept on kissing and caressing, I massaged her beautiful breasts, cupping each one gently underneath and running my tongue around her nipples. Kneeling beside her, I kissed slowly down from her nipples, down her stomach and stopped to focus on her belly button. I next began to run my fingers under the waist band of her white cotton panties. I kept one hand at the waist band and brought the other from her breast to her pussy, and cupped it. I began rubbing my hand back and forth, her arousal was obvious. She took my hand and helped to guide off her panties. I spread her out her legs some, and she let out a deep sigh. Once completely naked she brought her finger down to her pussy and parted the tender folds while spreading her legs wider. She asked me to eat her pussy and as I hungrily did as she began to rub her clit! Her aroma and taste was so intoxicating!!! I licked and suckled, finally inserting my tongue deep between her lips. I could tell that she was enjoying herself as she squirmed with delight. That made me feel so happy that I was bring her such pleasure! I stopped at one point, looked up at her wanting to make sure what I was doing met with her approval. She sighed, ‘oooohhhh yessss!!!”
With that pause she sat up and said that it was her turn to pleasure me. She reached over and pulled off my briefs maneuvering them over my erection. I laughed as she worked them off. Once I was naked she kneeled in front of me and took my cock in her hand. She gently kissed and circled my tip with her tongue, and licked down the shaft before my whole cock disappeared in her mouth. She went back and forth as I held her head and watched it slide in and out of her lips. I then pulled her head away and I laid her back and began to slide my cock between her soaked pussy lips. I did that for a minute or two and then placed the tip of my cock at the opening of her dripping wet pussy and started to tease her by poking the tip just inside of her opening. After a few more minutes of listening to her sighs of pleasure she said, ‘I want you inside of me, I can’t wait any longer!!!’ I whispered, ‘ then I guess its time,’ and pulled cock away giving her a long wet kiss.
We were both breathing heavy as we fumbled with our contraceptives. And yes, talk about spoiling the mood! I never put one on before and I suppose I should have tried beforehand. I unwrapped one and tore it trying to slid it down my shaft. Elizabeth helped me with the second one. She gave me some quick head and mentioned that she like the smell and taste of her pussy. Then she slid the condom down the shaft effortlessly. As for her, she filled a tube with a gel, inserted and squeezed it in. It was very sexy to watch her do it!
We both took a sip of wine and began to kiss deeply. I laid her back on the bed and she spread her legs about as wide as she could and drew up he legs a bit. I maneuvered myself between her legs and began to kiss her moving between her lips, neck, breasts and belly. We were both very sweaty and I loved her salty taste! I felt Elizabeth take hold of my cock and place it at her opening. I gave her another long kiss with plenty of tongue, pulled away and we both stared into each other’s eyes as I began to push into her. She was very lubed up and I could went in fairly easily to just past my tip. Her pussy was so tight and I loved the warmth. As I slid in, Elizabeth closed her eyes to enjoy the feeling but, waiting for the pain. I could understand her concern. I could only get my cock inside about an inch or so past the tip and then I felt some resistance. I slowly tried to pushed inside of her but, I sensed a bit of pain and discomfort. I kept pushing at her direction. After that did not seem to work, I used smaller, gentle thrusts and after about 10 minutes I felt Elizabeth pull back a bit as I began to tear her hymen. After a bit more I had full penetration and at last she was fully open and we were virgins no longer! Now we both focused only on the pleasure of the moment. After a few more thrusts, Elizabeth said that she wanted to see, so we sat up a bit and maneuvered in such a way that she was sitting on my lap facing each other. She leaned back and we both had a sumptuous view of my cock in her pussy. There was more blood than we expected but the worst part was over. We hugged and smiled at each other. Elizabeth then rolled me over and she was now on top. She guided my cock into her opening and once deep inside, Elizabeth began to slowly bounce on top sliding me in and out from the base to the tip then slowly plunged it back in We began kissing and I held onto her breasts to minimize the bounce. She continued gently pumping, with a very relaxed and fluid rhythm. I kept fondling her breasts and watching my cock slide in and out. I was starting to come! Then I noticed that the condom had torn. I told her I needed a new one. She pulled off me, removed the condom and quickly slid my cock back in. The feeling without the condom was so different and wonderful. With that I began to meet her thrusts and in the middle of my panting I told her I was coming. I guess she had second thoughts and pulled off just as I came! I let out a long aaaaaaaaaahhhhhhhh shooting my load straight up like a geyser. After many large eruptions I looked up and she was covered with cum, we both were! We smiled and laughed. We then both collapsed into each others arms and fell a sleep. Elizabeth didn’t orgasm that night.
The next morning we woke up late and talked about the previous night (we had also forgotten to celebrate my B-Day but, I didn’t care!). When we went to our respective bathrooms to clean up we found a bowl of fresh strawberries and a nice bottle of Champaign with a note that just read Congrats!, Love Susan.
Later that day, I had to leave on the 3 o’clock bus. At the bus stop we kissed good-bye and as we did Elizabeth put my hand up her skirt and placed my hand on her bare, wet pussy and said, ‘come back next weekend, you owe me an orgasm!’ I did indeed return, and early at that!!