shy28boy's Blog

Stole this from one of my favorites

1. Do you make your bed everyday? nope

2. What's your favorite number? 28

3. What is your dream job? MC at a strip club

4. If you could, would you go back to school? yup, seeing the coeds running around campus would make it worth it

5. Can you parallel park? Y

6. Name a job you had which people would be shocked to know you had? Tellemarketing credit card application

8. Can you drive a stick shift? Y

9. What is your guilty pleasure? Erotica

10. What's your dream car? C8 Chevy Corvette Convertible

11. Do you talk to yourself? Y

12. Do you like doing puzzles? Y

13. Favorite music? Radio top hits, classic rock

14. Coffee or tea? Coffee

15. Do you hit the snooze button? You bet

16. Love or money? Love

17. Pets? Mix rescue dog

18. First thing you remember you wanted to be growing up?

This happened a long time ago but i still remember it well. I had gone on a weekend with my first true girlfriend and we were staying at a nice hotel. We had a nice round of sex where I had orgasmed. Then we started round number 2 and after a while I was on top pumping away but was not able to cum. I kept pumping and said I really want to cum. My girlfriend wispered back "I want you to cum, cum inside me" I guess that was this spark I needed so i felt my feet tingling and then more of my body and finally a long. extremely pleasurable orgasm! Still smile thinking about it.

Earlier this year, pre covid, we went to St. Marteen. They have a be called sunset beach, it is famous for being right at the end of the island runway and planes come in really close to land.

Any way there are nice bars on both ends of the beach. We go to one and it starts to rain so everyone is crowded together. One of the couples near us has a very attractive woman who is wearing a thong. Now we are sitting at a picnic table (the bar serves food) and thong girl sits on the table we are sitting at wearing her thong. All I could think was a little extra sauce for the next patrons burger....

I just went on a cruise recently and had a lot of fun. One of my favorite parts is going to the hot tub and talking and looking at the lovely ladies in the hot tub in there swim suits. Love the cleavage and then the beautiful legs and asses when the get in an out of the tub! I always am wearing my sunglasses so I can stare without if being so obvious! I get plenty of material to play back in my mind for later masturbation sessions!

I got divorsed (my ex wanted it, I was devasted) and ended up not having sex for a few years. I finally felt better about myself and met someone at a social event. I got her number and we agreed to go out.

The first time was a fun date but things got more interesting on the second date. end

My friend lived in a two bedroom apartment with another lady. After the we got back from dinner and we drove back to her place, I asked if I could come in for a cup of coffee. She agreed and we went to the apartment and she made me coffee while I sat on her couch. She came back with the coffee and after having a few sips I leaned in to kiss her and she responded with a nice kiss back. The kissing turned into her stradling me while kissing and me feeling her beautiful breasts and that was the extent of it that date.

The next date things got a little more daring. I think we started kissing again on the couch and she agreed to go to her bedroom. I believe that we both ended up semi naked, I am sure she got down to just her panties but can't say for sure whether they ever came off or not. They next date was even more interesting. After making out a while we were both naked and horny. For some reason, I was able to put on a condom, I think I said something like if I came while we were fooling around, the cum wouldn't get every where. So while we were fulling around, my cock accidnetially slipped into her wet pussy (it was truely not on purpose!) It was just the tip in a rubber but it felt great. We didn't get furhter that night, I think she ended up jerking me off.

On our next date I was fairly certain that my long dry spell was going to end so I brought the condoms along again. We again ended up naked and horny and this time. We started the makeout session and in due time we were both naked and horny. This time when I put on the condom, she said it was ok to enter her. When i slowly stuck it in it felt so damn great, her pussy snuggly enveleped over my still cock. Your truely never miss something until you loose it and the feeling you have when you regain it again is so fucking great. I think i didn't last too long, had a wonderful orgasm. I had some more condoms with me so after a timeout, we went at it again and I lasted a lot longer that time.

I lost my virginity at 25, not for lack of trying but I think I was a little too shy to close the deal. Anyway, by the time I was 25 I was determined to loose the V card.

I put in a personal add in Boston Magazine (way, way per match/tinder.com) and got a view responses. I went out on one date and it was a disaster. I then went out with a second girl, a blonde who had just graduated from college and had her own studio apartment.

The first date went well, we went out to dinner and had a nice conversation and just a chaste kiss when the evening ended. The second date was much more interesting. We went to dinner or a movie and then back at her place. We started kissing on the couch which turned into breast play, her blouse coming off and eventually both our pants/skirts came off. I was naked and she was done to her nylons on (this was the 80s, the ladies were all wearing them) and panties underneith, sexy look btw. At that point i go my first blowjob to completion which also was the climax of that date.

So we set up another date which i was pretty certain i was going to loose the virginity. I believe we went to a movie, I don't remember what the film was. We got back to her place and the action began. Kissing on the couch which lead to touching and then clothes coming off. We finally ended up completely naked in her bed. At that point, she asked me are you sure you want to do this ? (I had told her I was a virgin earlier) She then went to the bathroom to put in a diaphram. While i was lying there, harder than I think I ever was, thinking to myself it is finally gonna happen.

She came back an slowly mounted me. As I slid into her the lovely feeling of warmth and tightness around my cock, I came immediately! I was so horny and young that I don't think I got soft at all! She went back to the bathroom to put in some more spermacide and then we went at it again, this time I lasted much longer. So mission accomplished in a loving and memoriable way.

This story occured when I was a very horney 20 something just out of college. One of my friends at the time had a girlfriend who was attending college out of state. Several of us convinced her to bring a bunch of co-eds with her that were looking for fun. The girls came up that Friday evening and we started a little drinking, there were 4 girls (including my roomies girlfriend) and 6 guys. The drinking started getting heavier and it was decided to play a game of I never. The game quickly degenerted to sexual questions (I drank myself and was the only one who did when I asked if anyone had used a tool when masturbating. People were getting pretty hammered and things were winding down. One of my friends had sneaked off (to my bedroom) with one of he girls. Everyone else had either passed out or left until there was just my friend and his girlfriend, the 2 other college girls and another friend. My friend tell me they are going back to they are all going back to his apartment and asks if I wanted to come with them. For some reason I still can't explain, I declined. My friend asked again, are you sure? and I again declined?

The next day I heard that my other friend got into a bit of hanky panky with one of the girls and the other girl was left alone! Great thinking on my part! Regrets to this day.