My first time ever having sex wasn’t all that good, actually. I was nervous. My first girlfriend was 3 years older than me. (21 to my 18) She did not want to get pregnant so she insisted on condom usage. She had been with a half-dozen guys before me, so she knew what she was doing more than I did.
Anyway, That Friday night when the time came, she put the condom on me, guided me inside of her… and about 15 seconds later I felt myself ejaculating into the condom but without having an orgasm. I stopped moving and she asked what was wrong.
:I think I’m done already." I told her. She reached down, squeezed the base of the condom and had me back out and sure enough, I was going soft and the condom was full.
I apologized, she said not to worry, first times are usually awkward, etc. So the next afternoon, I stop over before work, sit down at the kitchen table with my girlfriend and her mom, (she had recently moved back in with her parents to save some money) and the first thing out of her mom’s mouth is, "So, I hear you’re not a virgin anymore."
That was a little awkward. I didn’t know what to say. Then she says, "Don’t worry, it gets better after the first couple of times."
So there I sat, a little embarrassed for a while. Who knew she’d share the details with her mom?
So that night, after work, we went back to her house and tried it again. It started the same way… and pretty much ended the same way. I might have lasted a whole minute this time. Sex just felt different than I expected, I guess. My only experience so far had been masturbation and I couldn’t really feel a whole lot with the condom on, and I guess that combined with being nervous led to my being premature.
The next weekend I stopped over and she let me know she had her period and not to expect any bedroom activities that weekend. I hadn’t masturbated all week in case that was the reason for my lack of an orgasm with her. I continued to abstain from masturbation for the following week just in case. (I was 18 and really had no clue)
The following weekend, I stopped over at her house on Friday. They didn’t use the front door at her parent’s house but rather a back entryway that led to the garage and driveway so I usually just let myself in and said hello since they wouldn’t be able to hear anybody knocking. When I got there that afternoon, My girlfriend and her mom were in their enclosed front porch that doubled as a storage area and didn’t hear me come in. I sat down at the table and could hear them talking.
I heard her mom say, "If you find that spermicide, you really should let him try doing it without a rubber. I bet that’s why it hasn’t worked for you guys so far. Since you just finished your period, you should be fine if you use that foam stuff, too."
My girlfriend replied, "I’m not as worried about getting pregnant as I am about just doing it that way. I can’t stand having it ooze out of me all night afterwards."
Her mom said, "Why don’t you just ask him to pull it out at the end. You know, a lot of guys like doing it that way anyway."
"That would be kind of awkward, mom," She said, "Besides, I think he’s nervous enough about doing it already. I wouldn’t want to give him more anxiety by having to worry about that, too."
"Well, you never know if you don’t ask him." Her mom said as she walked out of the front porch.
As I heard her coming towards the kitchen, I got up and acted like I was just walking in. Just then I heard my girlfriend say, "I found it!"
"Found what?" I asked, to which her mom replied with a wink, "You’ll find out later tonight." as she walked by.
So later that night, after work, we went back to her place again. We started kissing, touching, caressing, etc. As we got undressed, my girlfriend said, "Tonight we’re going to try something a little different for you. Hopefully it will feel better for you. She brought out the package of spermicidal foam and said, "With this, we’ll be able to try it without a condom so it should feel more natural for you."
"Sounds good to me." I said. She then proceeded to turn of the lights. I heard her doing something with the spermicide, and then after a little while, she pulled me over on top of her and said she was ready. I was really looking forward to feeling what it felt like sliding it into her without a condom.
She had me get into position, rub it against her pussy a few times, and…
The next thing I knew. I was balls-deep inside her without a condom on.
Wow. A million times better than the last two occasions. It felt so much warmer, so much wetter. I started slow, thrusting at a steady rhythm. I was finally doing it right, and I was lasting more than 5 seconds. We actually kept at it for about 15 minutes until I started to feel that tingling sensation that tells me I’m about to explode. I remembered earlier in the day how she told her mom that she hated having it ooze out afterwards and how her mom said to just have me pull out, so as I felt it was just about to happen, I reached down, pulled it out, and just let it spray out all over her.
The lights were off and it was dark in the room, so I couldn’t see where I was aiming, but after I was done, she reached over and turned the bedside lamp on.
Oops. It still ended up being pretty messy. But she just grabbed the shirt she had been wearing and used it to wipe all of it up.
"I wasn’t sure if you wanted all of that inside you or not," I explained as she was cleaning it up.
"That was just fine." She replied. Then she asked, "Did it feel good for you this time?"
I replied that it did. She then said, "I figured it did, considering what a mess you made. That was a lot."
I was just happy to finally have had regular sex that lasted for more than 15 or 30 seconds.
I never spent the night there, since she still lived with her parents, so I made my way home a little while later.
The next day, I stopped over, and sat at my usual spot at the kitchen table.
When my girlfriend sat down, her mom asked, "So did it work for the two of you last night?"
"Oh, yeah." My girlfriend replied. Her mom asked me, "Did you like it better that way? Were you able to… You know? have a normal ending?"
"I did." I replied. She then asked me, "Was it good for you?"
"I’ll answer that and say it was." My girlfriend replied. "You can definitely tell he’s 18. You know what they say about 18 year old boys."
"Was it too messy for you?" her mom asked. "Or did you break down and ask him to pull it out at the end?"
"I didn’t ask him to," said my girlfriend, "He did it all on his own. And it ended up all over me, from my belly button all the way up to my neck."
"Oh, wow!" Her mom replied. "Well, I’m glad you two had fun anyway. Are you planning on doing it again tonight?"
"Maybe," She answered. "I think there’s enough spermicide left for one more try."
So after work, we ended up in her bedroom again. We tried it again pretty much the way, with pretty much the same result, only not as much came out at the end.
But that weekend was the last time she let me do it without a condom. After that, it was condoms every time for the next 3-1/2 years until we split up.
But at least I got to enjoy that weekend and my 3rd and 4th time.
The end.