Male and Virgin at 29

I almost made it to 30 years of age before losing my virginity. Almost.

In high school I was a nerd, hanging out at the science building and building rockets on the weekend. I was too shy to socialize with girls. I was very much afraid of doing something that might accidentally offend. Somehow this turned into a very rigid inhibition, a sort of 'Good boys don't'.

And that is how I lived my life; never flirting or making physical contact with women except for obligatory hugs with one lady friend. I was not happy that I could possibly face a life of celibacy, but I was too shy, inhibited and socially inept to change it.

I think I knew that some women liked casual sex, but they hung out with jocks or people who were good at socializing, not in my part of the world.

Then a trip to San Francisco began a year that pushed my boundaries and sent me into free fall.

Meagan

When I left the Air Force I hired onto a swing shift job in Orange, California. After work I would stop in at the local clubs where a friend's cover band was playing, catch the last set or two and join the band for 'breakfast' at a local chain restaurant. The band had a drummer, bass guitar, my friend on keyboard and a female vocalist named Meagan.

Meagan was short with dark curly hair, well proportioned and looked hot in the outfits she wore on stage. I socialized with her a bit once or twice, driving her from the gigs to restaurants in my old Triumph GT6+ and once inviting her to dinner at a very nice restaurant in South Coast Plaza. It was all very arms length and proper.

I do not remember how it came about, but one night as I drove Meagan from a gig to a restaurant I admitted I was virgin. I still have a visual of that moment.

A month before my 30th birthday the band had a gig at a hotel near San Francisco airport and I decided to join them. We planned that I would room with my pianist friend so I could afford the stay.

Here the plot thickens.

My brother and his wife, Laurie, learned I would be in San Francisco and asked me to pick them up at the airport two days after I arrived there. I was to drive them down to Carmel and Monterey where we would stay a couple of nights while I showed them around the area.

I was puzzled that they knew of my plans as I had not told them and they did not socialize with the band members.

So I drove up to the hotel at the San Francisco airport, settled into my friend's room and went to watch the band play, grab a bite to eat and have a drink. As I sat sipping the drink, three women approached and asked if they could sit at my table. That was slightly curious as there were empty tables, but I welcomed them. The woman who had asked to sit at the table introduced herself as Betty.

As I settled back to watch the band, Betty began making very unsubtle advances. I politely deflected. After about thirty minutes of this she seemed frustrated and asked me to take her to her room. I thought briefly that being virgin I didn't have the slightest idea of what to do if I were to take her to her room. It was just too much for this shy nerd and I was looking for an out when Meagan came over to the table.

Meagan had finished her sets with the band and joined us for some small talk. After 30 minutes or so Meagan rose to go to her room and placed something on the table next to me. As she walked away I looked down to see she had left a key to her hotel room.

I felt instant panic. This could not be real. Why would these two women invite a shy, up tight man like me for casual sex? I thought I must be misunderstanding something. I felt that I had to go to Meagan's room out of courtesy, but I was sure I was misreading her intent and would end up looking like a fool.

I got in the elevator and all the way up repeated in my mind, "I know what's happening, but I must be misunderstanding something," over and over like a mantra.

When I got to Meagan's room I did not use the key to open the door. I knocked.

Meagan opened the door and invited me in, an unreadable expression on her face. I entered and went over and sat on the foot of the bed. Meagan sat near the head of the bed and looked at me, waiting. I sat there with my mind in a mess, trying desperately to think what to say.

After a while Meagan came to me at the foot of the bed, embraced me and gave me a long kiss full of promise. I had never before had a sensual kiss. I hadn't misread Meagan's intentions; she was going to have a virgin tonight.

As we undressed I stared at Meagan's trim small body and pert breasts. My eyes dropped to the top of her thighs. I had never seen a nude woman other than in photos. I forgot to breathe and then breathed deep anxious breaths.

We got in bed and held each other. I had no idea what I was supposed to do so I copied Meagan's moves, very slowly running my hand down her back to her firm tush, down her thighs, back up over her back and neck, and into her hair while holding her close.

Meagan put her hand on my penis and found I was not fully aroused. She said softly that we should go to sleep and see what happens in the morning.

Meagan probably thought I'd had too much to drink to become aroused. Actually it felt unreal to me that these two women were asking me for sex. My tidy, sterile little world was imploding and I felt somehow vulnerable.

Sleeping with Meagan was one of the most beautiful experiences of my life. I'd never slept with another person, never cuddled. As she lay next to me I could feel the warmth of her and the curves of her body.

I felt my barriers slipping away and cuddled closer. I fell asleep.

When I woke in the morning Meagan had one hand caressing my chest, her other hand around my very rigid penis. It had awakened before I did for my usual morning erection and they were patiently waiting for me.

We held and stroked each other for a few minutes then Meagan pushed against my chest and told me to lay on my back. She rose up, put one leg over me and straddled over my very firm erection, her breasts swaying ever so slightly as she moved. I looked at Meagan and every nerve in my body begged to feel her touch.

I took my penis by the base and moved it toward her. As I touched her, Meagan laughed softly and said, "Not THAT hole." She pushed my hand away and held my erection and moved it to her. I don't know whether she did it intentionally, but as she moved me to her she seemed to touch every possible sensitive spot.

I watched and felt the tip of my penis brush the lips of Meagan's vagina and then a sense of warmth, moisture and caress as I began to enter. Internally I was writhing with passion. Meagan lowered herself onto me, taking me into her. I felt I was going to explode.

Less than half way in I did explode.

For some reason I sort of apologized that it would be a few minutes before the next climax. Meagan continued to lower herself until she sat down on me fully, the weight of her body pushing me deep, deep into the moist warmth of her while her labia spread to embrace the base of my erection.

Saying, "You must've read a lotta books," she laughed softly and appreciatively and continued to use me to pleasure herself, grinding her clitoris against my pubic bone.

My body tensed up, all my attention on Meagan and my sense of her vagina around my penis. My hips twisted slightly and my legs moved to increase the pleasure. As I watched, Meagan seemed to focus on some private place deep inside her, tense up, quiver slightly, sigh and relax.

Then Meagan gave me a warm embrace and kiss and said, "If I didn't make a move, nothing would happen." It was a question.

"No," I replied.

Meagan laid down to go to sleep, but every part of my body was still screaming. I had to masturbate to relieve the tension.

This experience had turned my world upside down. I was very confused. Women actually wanted to have casual sex with me. What did Meagan expect now? I understood she maybe wanted to experience a virgin, but where did we go from there?

A friend of Meagan's named Holly had also been staying with the band. Later in the day Holly asked me to drive her to the airport and on the way I asked Holly if she knew why Meagan had sex with me. She gave no direct answer but, as we pulled up to the gate, Holly looked me in the eye with a sincere expression and told me not to get stuck on Meagan, to be open to other women.

Sherrie

As planned, the next day I went to the San Francisco airport to pick up my brother and Laurie for our stay in Monterey and Carmel. When they came down the corridor from the airplane there was a woman with them I'd never met. Laurie introduced me to Sherrie, one of her co-workers at the Huntington Beach police department.

We piled into my car and I drove down to Monterey where Laurie had reserved rooms. When we arrived at the motel, Laurie went to the desk to register our group. After the paperwork was done Laurie came over and gave me and Sherrie a key to the room we were to share.

THAT was unexpected!

I had that now familiar feeling of panic and confusion. I thought it was rude of Laurie to ask Sherrie to share a room, but I thought that I could be a gentleman and make sure everything worked out okay for Sherrie.

As Sherrie and I began walking towards the room, Laurie said, "Oh, I think the room has only one bed." I glanced at Sherrie and had dark thoughts about how Laurie could be so thoughtless as to put a friend of hers in a stranger's bed. How could she expect her friend to be good with that?

Having just lost my virginity I was still no genius in these matters. Obviously. After a while it began to dawn on me that Sherrie might be in on this surprise blind date. We had spoken little on the trip from San Francisco to Monterey so I had no clue.

That night as we readied for bed, Sherrie was not shy or modest. I tried not to stare at her full figure as she stood nude before slipping into bed, breasts swaying. We spoke little and Sherrie made no advances towards me so I climbed in between the covers where I would not touch her if she were not part of the plan.

The next morning we were all off to explore Monterey and Carmel. I had lived in the area and enjoyed showing them around.

While we were checking out the shops on Ocean Avenue in Carmel, Laurie took me aside and told me that Sherrie had asked whether I did not like her. Laurie told me that Sherrie was disappointed that I didn't have sex with her.

Sherrie was disappointed a total stranger didn't have sex with her?

I should have expected this, but I still managed to feel some surprise and disbelief. I was getting an engraved invitation. I was still feeling very shy and awkward, but I admit I did want more of what I'd experienced with Meagan.

That night Sherrie and I lay in bed nude. Meagan had taught me nothing about foreplay, what to say, what to do, so I floundered more than a bit. I ran my hands over Sherrie's ample breasts and lowered myself for my first taste of a woman's breasts since infancy. I licked and sucked Sherrie's firm nipples while she held me close, enjoying the sensation.

Then I dropped down and down for my first taste of a woman.

I ran my tongue between the soft labia, over Sherrie's clitoris and down into her vagina, feeling and sharing her pleasure as Sherrie responded by putting her hands in my hair and guiding me. Her inner labia lifted and spread as if proudly showing off Sherrie's vagina. Like arms wide open inviting me in.

I had long before become rock hard. Sherrie took me and guided me into her. For the second time I felt the warm, moist caress of a woman.

We shared a long and leisurely night, both of us enjoying orgasms. As I had with Meagan I found that being with Sherrie kept me so highly aroused that I could keep going without pause. This pleased Sherrie. She seemed insatiable.

When Sherrie finally turned over to go to sleep we went into the spoons position. I stayed inside, feeling her body changes as she fell asleep. Her vagina relaxed and her cervix came down to kiss the tip of my erection. Oh, my God. Oh. My. God.

As my body wound down for sleep, dozens of questions began crowding my mind, making sleep difficult. I tried to figure out why my very manipulative and controlling sister-in-law, Laurie, had set me up and how she had known about the trip.

Did Laurie know Meagan planned to take my virginity? Did Laurie intend to 'protect' me from Meagan by putting me in bed with Sherrie?

I've never gotten any answers. I still don't know how I should feel about the thought of women plotting about my virginity.

I drifted off to sleep.

After we had all returned to Southern California I saw Meagan only socially, but I frequently stayed with Sherrie. I learned about women's bodies and how to please women. I learned about foreplay. We had public sex on the balcony of Sherrie's apartment overlooking Huntington Beach.

I did not learn about flirting or seduction.

I did have my first experience with oral sex.

I enjoyed the feeling of the many small nubs on the surface of Sherrie's tongue teasing the pleasure points on my penis. For the most part it was just part of foreplay and casual. Then one day Sherrie seemed to be more aggressive about it. She ran her tongue over my erect penis in a way that surprised me.

This was something new. I became more and more aroused, twisting my hips at the feeling, knowing I was heading for an orgasm. I warned Sherrie that I was having trouble not climaxing, but she continued with even more intensity until I exploded in her mouth.

After a while Sherrie got up and said, "I have my period today. We don't both need to do without." I settled back amazed at this new experience.

As I've mentioned, Sherrie always seemed insatiable. One day I decided to push her all the way and give her as much pleasure as she was capable of receiving. I wanted to leave her limp with satisfaction.

I normally do not focus on orgasms for myself; I just enjoy the feeling of arousal and the orgasms happen when they happen. But that night I decided to focus on my orgasms to learn how far I could go.

It was a marathon session of sex. I had an orgasm each time Sherrie did. After the spasms of the fourth orgasm faded I said softly, "Wow, I've had the same number of orgasms as you."

This was the wrong thing to say. Sherrie said she was done. Then I realized that Sherrie was not actually insatiable, but felt obligated to be there for her man.

Oh.

Cindy

About this time I also realized what was behind the endless articles on premature ejaculation and desensitizing creams: not all men keep an erection through a series of orgasms. In fact I could not find information on men who do.

I began sometimes not so subtle questions to co-workers about their sex patterns. One co-worker decided to question my claim that some men have serial orgasms. He and his girlfriend set up a blind date with a young lady named Cindy who was to sleep with me, take notes and report back.

I agreed to the date, picked Cindy up after our swing shift and took her to a nearby restaurant on top of a hill in Orange. They were no longer serving food so we sat on the deck overlooking the Orange city lights and had a drink. We sat next to a fire and chatted and got to know something about each other.

We did not talk of sex or the reason for the date so I began to be unsure whether Cindy was really in on it. We left the restaurant and as I drove Cindy to her apartment I asked her if she wanted a visitor for the night. She said she did.

I don't remember much of Cindy's apartment other than her bedroom. A bedside lamp cast a pool of light across the pillows as we undressed without conversation.

I decided that if this date was to take notes on my performance I was going to give her something to report. I walked up behind Cindy where she stood taking off her bra, pushed my hands down into her panties and held her buns. I slid my hands around her hips to run my fingers between her labia. I was surprised to find them very wet and the crotch of her panties soaked.

Well! Meagan had been matter of fact, Sherrie had been available, but not an initiator. Cindy was something new: eager and hungry. My education was clearly not done.

I nuzzled into Cindy's neck and ran my hands upward over her very nice, slim body. Her proud and pert breasts welcomed my touch with erect nipples. Then slowly back down over her belly, down her thighs and to the insides of her thighs to let my fingers enjoy the sensation of stroking the soft and wet labia.

We went to the bed and Cindy lay on her back with her knees raised. I spread her knees and slowly ran my cheek along the inside of her thighs and down to kiss her clitoris. Cindy was eager for the touch, arching her back and pulling my face into her. I responded to the feel of her labia on my tongue and pushed in closer.

Then I moved up and Cindy pulled me into her. She grabbed my buttocks and demandingly pulled me all the way in. She pushed my hips away slightly and then forcefully pulled my buttocks in again and again. Then Cindy spread her legs wide and I raised up a bit on my hands and knees so I could watch myself plunging into her.

I fell into Cindy's rhythm while she kept her hands firmly on my buttocks. I exploded with one of the strongest orgasms I'd had while Cindy arched her back and again pulled on my buttocks with a new, more urgent, almost violent rhythm that released her own orgasm.

Cindy began a more relaxed rhythm and massaged her clitoris as we both again went to orgasm. Then she seemed to relax and give her body to me for my pleasure. I could sense she was luxuriating in the touch, her body making languid, almost dance like responses to my every move. I took my time and savored every sensation as I explored deep in Cindy's vagina, moving around slowly, staying all the way in rather than thrusting until I reached an orgasm so strong I didn't even notice whether I had ejaculated.

In the morning I caught a look at myself in a mirror as I was leaving. I was a mess, but had to go. I kiddingly asked Cindy what the neighbors would think seeing me leave her apartment so disheveled. Her reply was, "That you got what you deserved."

I have never figured out what Cindy meant and have never seen her again to ask. Nor did my co-worker ever tell me what Cindy reported.

Ann

I had always felt sex should be part of a relationship and not something casual or for recreation. I was grateful to Meagan for helping me lose some inhibitions, but began feeling that the casual sex was getting in the way of learning how to develop a deep, meaningful relationship.

About six months after my night with Meagan, I became interested in Ann, a co-worker I'd often chatted with at the office. Ann is a beautiful woman who could have her pick of the guys in the office, but somehow we found that we enjoyed chatting. Maybe because we were both sort of oddballs or black sheep.

Ann felt special to me. Our casual relationship was relaxed, honest and open. After a while I knew I wanted to have a deeper, intimate relationship with her. I didn't want to do anything to offend Ann or make her uncomfortable about being with me so I reverted back to my "don't flirt, don't touch" behavior.

We began seeing each other outside work and I invited Ann on an overnight date to the Renaissance Pleasure Faire in Novato. After she accepted the date I realized I had not told Ann we would be staying in separate rooms and panicked. I didn't know whether Ann would expect casual sex in an overnight date and, like Sherrie, be disappointed if we did not have sex.

We drove up to Novato early and spent most of the late morning and afternoon at the Pleasure Faire, enjoying the forest setting, the costumes, the music, the artists' wares and the rasty behavior on the stages. By the late afternoon we were beat from the long drive and hours of walking around the Faire's dusty forest setting. We headed to the motel where I had reserved two separate rooms for the overnight stay. All went well.